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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (1) Show 5 proteins XML

enzymes (4)transporters (1) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:43 UTC

HMDB ID

HMDB0014744

Secondary Accession Numbers

HMDB14744

Metabolite Identification

Common Name

Cyclothiazide

Description

As a diuretic, cyclothiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like cyclothiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of cyclothiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. Cyclothiazide is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. It is also indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effectiveness of other antihypertensive drugs in the more severe forms of hypertension.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014744
     RDKit          3D
Cyclothiazide
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.2302    1.2480    0.3513 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7176   -0.3788    0.6783 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.3575   -1.3414   -0.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -0.6967    2.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635   -0.4465    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139    0.6887    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.5421    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2607   -0.6756    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -1.8153    0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -1.6789    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3604   -3.0937    1.2013 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1541   -0.7670    0.4920 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    0.0269   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -0.5040   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    0.2123   -1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968    0.3928   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.9509   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.4267    0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764   -0.4585    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    0.8461    0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    1.4179   -0.1225 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.9072   -0.0344 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.9263    2.8385    1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    2.6821   -1.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    1.8831    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228    1.5102   -0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127    1.6351    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -2.7740    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.4419    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5416   -0.1073   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -1.5723   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    1.2219   -1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -0.4083   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2420    1.0670   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -1.4611   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847   -2.3067    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379   -0.5058    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549    1.7012    0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4882    0.9675    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622    2.0226   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  2  0
 10  5  1  0
 19 14  1  0
 22  7  1  0
 20 16  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

606
  Mrv0541 02231214482D          

 24 27  0  0  1  0            999 V2000
    8.5685    0.7911    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7726   -0.8120    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5685   -0.8311    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.1686   -1.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3766   -1.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9672   -0.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1698   -1.5154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867   -0.4160    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7726    0.7719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2529   -1.2298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4009    0.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708    0.3620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1849    0.7580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1959    1.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0473    1.7208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698   -1.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -0.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4585    0.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4585   -0.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665    0.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1665   -0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8842   -0.4325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8842    0.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 24  1  0  0  0  0
  2  4  2  0  0  0  0
  2  5  2  0  0  0  0
  2  8  1  0  0  0  0
  2 20  1  0  0  0  0
  3  6  2  0  0  0  0
  3  7  2  0  0  0  0
  3 10  1  0  0  0  0
  3 23  1  0  0  0  0
  8 16  1  0  0  0  0
  9 16  1  0  0  0  0
  9 19  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 11 16  1  0  0  0  0
 12 15  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 18  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014744

> <DATABASE_NAME>
hmdb

> <SMILES>
NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)

> <INCHI_KEY>
BOCUKUHCLICSIY-UHFFFAOYSA-N

> <FORMULA>
C14H16ClN3O4S2

> <MOLECULAR_WEIGHT>
389.878

> <EXACT_MASS>
389.027075102

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.09544582533753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{bicyclo[2.2.1]hept-5-en-2-yl}-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

> <ALOGPS_LOGP>
1.32

> <JCHEM_LOGP>
0.9439138553333333

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.772778408192679

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.061499967049983

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5425274919414873

> <JCHEM_POLAR_SURFACE_AREA>
118.36

> <JCHEM_REFRACTIVITY>
92.6485

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclothiazide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014744
     RDKit          3D
Cyclothiazide
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.2302    1.2480    0.3513 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7176   -0.3788    0.6783 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.3575   -1.3414   -0.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -0.6967    2.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635   -0.4465    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139    0.6887    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.5421    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2607   -0.6756    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -1.8153    0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -1.6789    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3604   -3.0937    1.2013 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1541   -0.7670    0.4920 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    0.0269   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -0.5040   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    0.2123   -1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968    0.3928   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.9509   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.4267    0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764   -0.4585    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    0.8461    0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    1.4179   -0.1225 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.9072   -0.0344 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.9263    2.8385    1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    2.6821   -1.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    1.8831    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228    1.5102   -0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127    1.6351    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -2.7740    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.4419    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5416   -0.1073   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -1.5723   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    1.2219   -1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -0.4083   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2420    1.0670   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -1.4611   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847   -2.3067    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379   -0.5058    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549    1.7012    0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4882    0.9675    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622    2.0226   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  2  0
 10  5  1  0
 19 14  1  0
 22  7  1  0
 20 16  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 606                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      15.995   1.477   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      10.776  -1.516   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0      15.995  -1.551   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0      11.515  -2.796   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.036  -2.796   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      16.739  -0.274   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      15.250  -2.829   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       9.495  -0.777   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      10.776   1.441   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      17.272  -2.296   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       8.215   1.441   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.359   0.676   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.078   1.415   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.832   2.869   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.822   3.212   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.495   0.702   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.237  -2.033   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.957  -1.293   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.056   0.702   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.056  -0.777   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.377   1.492   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.377  -1.567   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.717  -0.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.717   0.733   0.000  0.00  0.00           C+0
CONECT    1   24                                                            
CONECT    2    4    5    8   20                                             
CONECT    3    6    7   10   23                                             
CONECT    4    2                                                            
CONECT    5    2                                                            
CONECT    6    3                                                            
CONECT    7    3                                                            
CONECT    8    2   16                                                       
CONECT    9   16   19                                                       
CONECT   10    3                                                            
CONECT   11   12   14   16                                                  
CONECT   12   11   15   17                                                  
CONECT   13   14   15   18                                                  
CONECT   14   11   13                                                       
CONECT   15   12   13                                                       
CONECT   16    8    9   11                                                  
CONECT   17   12   18                                                       
CONECT   18   13   17                                                       
CONECT   19    9   20   21                                                  
CONECT   20    2   19   22                                                  
CONECT   21   19   24                                                       
CONECT   22   20   23                                                       
CONECT   23    3   22   24                                                  
CONECT   24    1   21   23                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0014744
HETATM    1  N1  UNL     1       6.230   1.248   0.351  1.00  0.00           N  
HETATM    2  S1  UNL     1       5.718  -0.379   0.678  1.00  0.00           S  
HETATM    3  O1  UNL     1       6.357  -1.341  -0.253  1.00  0.00           O  
HETATM    4  O2  UNL     1       6.202  -0.697   2.078  1.00  0.00           O  
HETATM    5  C1  UNL     1       3.964  -0.446   0.613  1.00  0.00           C  
HETATM    6  C2  UNL     1       3.214   0.689   0.334  1.00  0.00           C  
HETATM    7  C3  UNL     1       1.851   0.542   0.303  1.00  0.00           C  
HETATM    8  C4  UNL     1       1.261  -0.676   0.538  1.00  0.00           C  
HETATM    9  C5  UNL     1       2.013  -1.815   0.818  1.00  0.00           C  
HETATM   10  C6  UNL     1       3.365  -1.679   0.851  1.00  0.00           C  
HETATM   11 CL1  UNL     1       4.360  -3.094   1.201  1.00  0.00          CL  
HETATM   12  N2  UNL     1      -0.154  -0.767   0.492  1.00  0.00           N  
HETATM   13  C7  UNL     1      -0.935   0.027  -0.448  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.333  -0.504  -0.427  1.00  0.00           C  
HETATM   15  C9  UNL     1      -3.283   0.212  -1.365  1.00  0.00           C  
HETATM   16  C10 UNL     1      -4.497   0.393  -0.478  1.00  0.00           C  
HETATM   17  C11 UNL     1      -4.950  -0.951  -0.046  1.00  0.00           C  
HETATM   18  C12 UNL     1      -4.114  -1.427   0.906  1.00  0.00           C  
HETATM   19  C13 UNL     1      -2.976  -0.458   0.930  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.784   0.846   0.811  1.00  0.00           C  
HETATM   21  N3  UNL     1      -0.836   1.418  -0.122  1.00  0.00           N  
HETATM   22  S2  UNL     1       0.821   1.907  -0.034  1.00  0.00           S  
HETATM   23  O3  UNL     1       0.926   2.839   1.157  1.00  0.00           O  
HETATM   24  O4  UNL     1       1.252   2.682  -1.229  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.763   1.883   1.034  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.923   1.510  -0.613  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.713   1.635   0.153  1.00  0.00           H  
HETATM   28  H4  UNL     1       1.512  -2.774   1.003  1.00  0.00           H  
HETATM   29  H5  UNL     1      -0.626  -1.442   1.171  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.542  -0.107  -1.477  1.00  0.00           H  
HETATM   31  H7  UNL     1      -2.335  -1.572  -0.745  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.946   1.222  -1.650  1.00  0.00           H  
HETATM   33  H9  UNL     1      -3.546  -0.408  -2.246  1.00  0.00           H  
HETATM   34  H10 UNL     1      -5.242   1.067  -0.825  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.821  -1.461  -0.444  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.285  -2.307   1.482  1.00  0.00           H  
HETATM   37  H13 UNL     1      -2.338  -0.506   1.777  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.155   1.701   0.582  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.488   0.968   1.636  1.00  0.00           H  
HETATM   40  H16 UNL     1      -1.262   2.023  -0.859  1.00  0.00           H  
CONECT    1    2   25   26
CONECT    2    3    3    4    4
CONECT    2    5
CONECT    5    6    6   10
CONECT    6    7   27
CONECT    7    8    8   22
CONECT    8    9   12
CONECT    9   10   10   28
CONECT   10   11
CONECT   12   13   29
CONECT   13   14   21   30
CONECT   14   15   19   31
CONECT   15   16   32   33
CONECT   16   17   20   34
CONECT   17   18   18   35
CONECT   18   19   36
CONECT   19   20   37
CONECT   20   38   39
CONECT   21   22   40
CONECT   22   23   23   24   24
END

HMDB0014744
     RDKit          3D
Cyclothiazide
 40 43  0  0  0  0  0  0  0  0999 V2000
    6.2302    1.2480    0.3513 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7176   -0.3788    0.6783 S   0  0  0  0  0  6  0  0  0  0  0  0
    6.3575   -1.3414   -0.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2023   -0.6967    2.0777 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9635   -0.4465    0.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139    0.6887    0.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8510    0.5421    0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2607   -0.6756    0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0127   -1.8153    0.8183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3651   -1.6789    0.8508 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3604   -3.0937    1.2013 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1541   -0.7670    0.4920 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9349    0.0269   -0.4477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329   -0.5040   -0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2826    0.2123   -1.3649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968    0.3928   -0.4776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9496   -0.9509   -0.0462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1140   -1.4267    0.9063 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764   -0.4585    0.9296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    0.8461    0.8108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8359    1.4179   -0.1225 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8208    1.9072   -0.0344 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.9263    2.8385    1.1574 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2525    2.6821   -1.2290 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7634    1.8831    1.0339 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9228    1.5102   -0.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127    1.6351    0.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5117   -2.7740    1.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6259   -1.4419    1.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5416   -0.1073   -1.4768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3346   -1.5723   -0.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9462    1.2219   -1.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5455   -0.4083   -2.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2420    1.0670   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -1.4611   -0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2847   -2.3067    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3379   -0.5058    1.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1549    1.7012    0.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4882    0.9675    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2622    2.0226   -0.8590 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  2  0
  2  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 13 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  2  0
 10  5  1  0
 19 14  1  0
 22  7  1  0
 20 16  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
  9 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide	ChEBI
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide	ChEBI
6-Chloro-3-(2-norbornen-5-yl)-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide	ChEBI
Ciclotiazida	ChEBI
Cyclothiazidum	ChEBI
Anhydron	Kegg
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide	Generator
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-7-sulphamoyl-1,2,4-benzothiadiazine 1,1-dioxide	Generator
6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide	Generator
6-Chloro-3-(2-norbornen-5-yl)-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide	Generator
Ciclotiazide	HMDB

Chemical Formula

C₁₄H₁₆ClN₃O₄S₂

Average Molecular Weight

389.878

Monoisotopic Molecular Weight

389.027075102

IUPAC Name

3-{bicyclo[2.2.1]hept-5-en-2-yl}-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide

Traditional Name

cyclothiazide

CAS Registry Number

2259-96-3

SMILES

NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2

InChI Identifier

InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)

InChI Key

BOCUKUHCLICSIY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thiadiazines

Sub Class

Benzothiadiazines

Direct Parent

1,2,4-benzothiadiazine-1,1-dioxides

Alternative Parents

Substituents

1,2,4-benzothiadiazine-1,1-dioxide
Secondary aliphatic/aromatic amine
Aryl chloride
Aryl halide
Organosulfonic acid amide
Benzenoid
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Aminosulfonyl compound
Sulfonyl
Secondary amine
Azacycle
Organic oxide
Amine
Organopnictogen compound
Organosulfur compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzothiadiazine (CHEBI:31448 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014744)
Membrane (HMDB: HMDB0014744)

Source

Exogenous

Exogenous (HMDB: HMDB0014744)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Cyclothiazide Action Pathway (PathBank: SMP0000103)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	227 - 228 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.28 g/L	Not Available
LogP	1.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	1.32	ALOGPS
logP	0.94	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.06	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	118.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	92.65 m³·mol⁻¹	ChemAxon
Polarizability	37.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	173.407	30932474
DeepCCS	[M-H]-	171.049	30932474
DeepCCS	[M-2H]-	204.922	30932474
DeepCCS	[M+Na]+	180.061	30932474
AllCCS	[M+H]+	182.7	32859911
AllCCS	[M+H-H2O]+	180.1	32859911
AllCCS	[M+NH4]+	185.0	32859911
AllCCS	[M+Na]+	185.7	32859911
AllCCS	[M-H]-	175.5	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.36 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2405 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1928.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	267.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	130.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	116.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	401.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	496.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	348.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	997.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	368.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1209.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	311.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	356.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	392.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	296.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	188.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclothiazide	NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2	4918.5	Standard polar	33892256
Cyclothiazide	NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2	3242.8	Standard non polar	33892256
Cyclothiazide	NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2	3655.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclothiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	3656.1	Semi standard non polar	33892256
Cyclothiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	3371.2	Standard non polar	33892256
Cyclothiazide,1TMS,isomer #1	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	4671.0	Standard polar	33892256
Cyclothiazide,1TMS,isomer #2	C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	3548.1	Semi standard non polar	33892256
Cyclothiazide,1TMS,isomer #2	C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	3429.8	Standard non polar	33892256
Cyclothiazide,1TMS,isomer #2	C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	4851.3	Standard polar	33892256
Cyclothiazide,1TMS,isomer #3	C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O	3497.1	Semi standard non polar	33892256
Cyclothiazide,1TMS,isomer #3	C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O	3378.2	Standard non polar	33892256
Cyclothiazide,1TMS,isomer #3	C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O	5022.9	Standard polar	33892256
Cyclothiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	3519.3	Semi standard non polar	33892256
Cyclothiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	3576.3	Standard non polar	33892256
Cyclothiazide,2TMS,isomer #1	C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	4637.7	Standard polar	33892256
Cyclothiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O	3512.7	Semi standard non polar	33892256
Cyclothiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O	3505.8	Standard non polar	33892256
Cyclothiazide,2TMS,isomer #2	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O	4274.6	Standard polar	33892256
Cyclothiazide,2TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O	3496.5	Semi standard non polar	33892256
Cyclothiazide,2TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O	3487.4	Standard non polar	33892256
Cyclothiazide,2TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O	4588.4	Standard polar	33892256
Cyclothiazide,2TMS,isomer #4	C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C2	3414.0	Semi standard non polar	33892256
Cyclothiazide,2TMS,isomer #4	C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C2	3527.7	Standard non polar	33892256
Cyclothiazide,2TMS,isomer #4	C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C2	4718.9	Standard polar	33892256
Cyclothiazide,3TMS,isomer #1	C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	3442.9	Semi standard non polar	33892256
Cyclothiazide,3TMS,isomer #1	C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	3708.5	Standard non polar	33892256
Cyclothiazide,3TMS,isomer #1	C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	4207.8	Standard polar	33892256
Cyclothiazide,3TMS,isomer #2	C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O	3485.7	Semi standard non polar	33892256
Cyclothiazide,3TMS,isomer #2	C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O	3706.6	Standard non polar	33892256
Cyclothiazide,3TMS,isomer #2	C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O	4538.0	Standard polar	33892256
Cyclothiazide,3TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O	3387.9	Semi standard non polar	33892256
Cyclothiazide,3TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O	3654.1	Standard non polar	33892256
Cyclothiazide,3TMS,isomer #3	C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O	4234.3	Standard polar	33892256
Cyclothiazide,4TMS,isomer #1	C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C2	3420.4	Semi standard non polar	33892256
Cyclothiazide,4TMS,isomer #1	C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C2	3875.1	Standard non polar	33892256
Cyclothiazide,4TMS,isomer #1	C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C2	4213.2	Standard polar	33892256
Cyclothiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	3921.4	Semi standard non polar	33892256
Cyclothiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	3634.1	Standard non polar	33892256
Cyclothiazide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	4739.8	Standard polar	33892256
Cyclothiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	3835.8	Semi standard non polar	33892256
Cyclothiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	3662.0	Standard non polar	33892256
Cyclothiazide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	4956.9	Standard polar	33892256
Cyclothiazide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O	3756.9	Semi standard non polar	33892256
Cyclothiazide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O	3627.3	Standard non polar	33892256
Cyclothiazide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O	5121.7	Standard polar	33892256
Cyclothiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	4031.5	Semi standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	4078.3	Standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O	4703.2	Standard polar	33892256
Cyclothiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O	4019.4	Semi standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O	4015.2	Standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O	4349.7	Standard polar	33892256
Cyclothiazide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O	3942.8	Semi standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O	4023.9	Standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O	4657.7	Standard polar	33892256
Cyclothiazide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C2	3906.6	Semi standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C2	4041.5	Standard non polar	33892256
Cyclothiazide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C2	4813.4	Standard polar	33892256
Cyclothiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	4165.8	Semi standard non polar	33892256
Cyclothiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	4470.5	Standard non polar	33892256
Cyclothiazide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C2	4300.7	Standard polar	33892256
Cyclothiazide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S1(=O)=O	4128.8	Semi standard non polar	33892256
Cyclothiazide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S1(=O)=O	4490.8	Standard non polar	33892256
Cyclothiazide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S1(=O)=O	4601.5	Standard polar	33892256
Cyclothiazide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O	4068.1	Semi standard non polar	33892256
Cyclothiazide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O	4453.6	Standard non polar	33892256
Cyclothiazide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O	4364.0	Standard polar	33892256
Cyclothiazide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C2	4299.9	Semi standard non polar	33892256
Cyclothiazide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C2	4908.6	Standard non polar	33892256
Cyclothiazide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C2	4357.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclothiazide GC-MS (Non-derivatized) - 70eV, Positive	splash10-016u-9133000000-93e2b7d86e56b630140d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclothiazide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclothiazide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 10V, Positive-QTOF	splash10-0006-0009000000-a75423eac08147027ff0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 20V, Positive-QTOF	splash10-0596-0629000000-2e3acef52ea168edcc37	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 40V, Positive-QTOF	splash10-0uei-3691000000-be00a0c434bc4cd8b71b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 10V, Negative-QTOF	splash10-059i-0009000000-be104b4d7d376f5e3166	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 20V, Negative-QTOF	splash10-00fr-9707000000-ad653225ea24c021e331	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 40V, Negative-QTOF	splash10-004l-9000000000-2690cb233bbed98f3652	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 10V, Positive-QTOF	splash10-0006-0009000000-64cd4a4b5b37d098a23a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 20V, Positive-QTOF	splash10-0006-0009000000-6253f7a477fe74bfc21d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 40V, Positive-QTOF	splash10-052f-9644000000-7357e78e11d940fc0f75	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 10V, Negative-QTOF	splash10-000i-0009000000-733060bf4799a6320f93	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 20V, Negative-QTOF	splash10-000i-2009000000-66e570b5f08162e4e541	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclothiazide 40V, Negative-QTOF	splash10-004i-9640000000-f157eafa7f76c2f8ea73	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cyclothiazide Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00606	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00606	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00606

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2807

KEGG Compound ID

C12685

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyclothiazide

METLIN ID

Not Available

PubChem Compound

2910

PDB ID

Not Available

ChEBI ID

31448

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Carbonic anhydrase 1

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:: CA1
Uniprot ID:: P00915
Molecular weight:: 28870.0

References

Rammes G, Zeilhofer HU, Collingridge GL, Parsons CG, Swandulla D: Expression of early hippocampal CA1 LTP does not lead to changes in AMPA-EPSC kinetics or sensitivity to cyclothiazide. Pflugers Arch. 1999 Jan;437(2):191-6. [PubMed:9929558 ]
Rammes G, Swandulla D, Collingridge GL, Hartmann S, Parsons CG: Interactions of 2,3-benzodiazepines and cyclothiazide at AMPA receptors: patch clamp recordings in cultured neurones and area CA1 in hippocampal slices. Br J Pharmacol. 1996 Mar;117(6):1209-21. [PubMed:8882618 ]
Fleck MW, Bahring R, Patneau DK, Mayer ML: AMPA receptor heterogeneity in rat hippocampal neurons revealed by differential sensitivity to cyclothiazide. J Neurophysiol. 1996 Jun;75(6):2322-33. [PubMed:8793745 ]
Pirotte B, Podona T, Diouf O, de Tullio P, Lebrun P, Dupont L, Somers F, Delarge J, Morain P, Lestage P, Lepagnol J, Spedding M: 4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2, 4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors: design, synthesis, pharmacology, and structure-activity relationships. J Med Chem. 1998 Jul 30;41(16):2946-59. [PubMed:9685234 ]
Larson J, Le TT, Hall RA, Lynch G: Effects of cyclothiazide on synaptic responses in slices of adult and neonatal rat hippocampus. Neuroreport. 1994 Jan 12;5(4):389-92. [PubMed:8003661 ]

Enzyme Details

2. Carbonic anhydrase 2

General function:: Involved in carbonate dehydratase activity
Specific function:: Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:: CA2
Uniprot ID:: P00918
Molecular weight:: 29245.895

References

Liljequist S, Cebers G, Kalda A: Effects of decahydroisoquinoline-3-carboxylic acid monohydrate, a novel AMPA receptor antagonist, on glutamate-induced CA2+ responses and neurotoxicity in rat cortical and cerebellar granule neurons. Biochem Pharmacol. 1995 Nov 27;50(11):1761-74. [PubMed:8615854 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. Carbonic anhydrase 4

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:: CA4
Uniprot ID:: P22748
Molecular weight:: 35032.075

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Enzyme Details

4. Sodium/potassium-transporting ATPase subunit gamma

General function:: Involved in ion channel activity
Specific function:: May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase
Gene Name:: FXYD2
Uniprot ID:: P54710
Molecular weight:: 7283.3

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

Enzyme Details

1. Solute carrier family 22 member 6

General function:: Involved in ion transmembrane transporter activity
Specific function:: Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:: SLC22A6
Uniprot ID:: Q4U2R8
Molecular weight:: 61815.8

References

Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. [PubMed:10991988 ]

Showing metabocard for Cyclothiazide (HMDB0014744)

MOL for HMDB0014744 (Cyclothiazide)

3D MOL for HMDB0014744 (Cyclothiazide)

3D SDF for HMDB0014744 (Cyclothiazide)

3D-SDF for HMDB0014744 (Cyclothiazide)

PDB for HMDB0014744 (Cyclothiazide)

3D PDB for HMDB0014744 (Cyclothiazide)

SMILES for HMDB0014744 (Cyclothiazide)

INCHI for HMDB0014744 (Cyclothiazide)

Structure for HMDB0014744 (Cyclothiazide)

3D Structure for HMDB0014744 (Cyclothiazide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

Transporters

References