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enzymes (5) Show 5 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015325

Secondary Accession Numbers

HMDB15325

Metabolite Identification

Common Name

Brinzolamide

Description

Brinzolamide, also known as azopt, belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms. Brinzolamide is a drug which is used for the treatment of elevated intraocular pressure in patients with ocular hypertension or open-angle glaucoma. Brinzolamide is a very strong basic compound (based on its pKa). Due to the abundance of readily-bound erythrocytes and minimal known metabolism, Brinzolamide's whole blood half-life is very long (111 days). Following ocular instillation, the suspension is systemically absorbed to some degree; however the plasma concentrations are low and generally below the limits of detection (less than 10 ng/mL) due to extensive binding by tissues and erythrocytes. Inhibition of carbonic anhydrase in the ciliary processes of the eye decreases aqueous humor secretion and thus lowers the intraocular pressure in the anterior chamber, presumably by reducing the rate of formation of bicarbonate ions with subsequent reduction in sodium and fluid transport; this may alleviate the effects of open-angle glaucoma.The recommended frequency for topical application is two times per day. Brinzolamide is a carbonic anhydrase inhibitor (specifically, carbonic anhydrase II). This combination may be more effective than either medication alone. Use for the treatment of open-angle glaucoma and raised intraocular pressure due to either excess aqueous humor production or inadequate drainage of the humor via the trabecular meshwork. While definitive sites of metabolism have not been firmly established, there are several metabolites worthy of note. Brinzolamide is excreted primarily unchanged (60%) in the urine, although the renal clearance rate has not been definitively determined. N-Desethylbrinzolamide is also found in the urine along with lower concentrations of the inactive metabolites, N-Desmethoxypropylbrinzolamide and O-Desmethylbrinzolamide; exact levels have not been definitively determined. Oral administration is less-favored due to variable absorption from the stomach mucosa and an increased side-effect profile versus ophthalmic administration. N-Desethylbrinzolamide is an active metabolite of the parent compound, and thus exhibits carbonic anhydrase inhibitory activity (largely carbonic anhydrase-I, when in the presence of Brinzolamide) and also accumulates in the erythrocytes. Brinzolamide (trade names Azopt, Alcon Laboratories, Befardin, Fardi Medicals, ) is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

Structure

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

HMDB0015325
     RDKit          3D
Brinzolamide
 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.6848    3.9984    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313    3.3307    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    1.9696    0.2388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    0.9645   -0.1373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1853    0.8896    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.3077   -0.2201 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008   -0.1374    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501    0.4421    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.1751   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1492   -1.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809   -1.8723   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660   -0.9514   -1.2467 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.6248   -0.5665   -2.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321   -2.1647   -1.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.3668   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -2.7421   -0.7300 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -2.0605   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9174   -2.8460    0.3586 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.6652   -3.4846   -1.0321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7901   -1.9353    1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5455   -4.0256    1.2506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214   -0.7532    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -0.3947   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.6447    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2922    4.1129    0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030    3.8900    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    3.6092   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4018    1.8349    1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8259    1.1734   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038    0.2461    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499    1.8730    0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810   -1.2649    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    0.0052    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3342    0.0026    1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589    1.5444    0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    0.6758   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    0.7195   -1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2259   -2.9563   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696   -1.8659    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -1.5142   -0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5946   -3.0163   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -3.3638   -1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575   -0.0644    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
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  6 12  1  0
 12 13  2  0
 12 14  2  0
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 23  4  1  0
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 19 43  1  0
 22 44  1  0
M  END

1194
  Mrv0541 02231215182D          

 23 24  0  0  1  0            999 V2000
    5.9370    1.4991    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321    1.3379    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7386    0.6740    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3495    2.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5245    2.2135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7386    1.4991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7386   -0.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0865    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.9760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5636    0.6740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.1510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2224    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4321    0.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9136    0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
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 14 15  2  0  0  0  0
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 16 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 21  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015325

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N3O5S3/c1-3-14-10-8-15(5-4-6-20-2)23(18,19)12-9(10)7-11(21-12)22(13,16)17/h7,10,14H,3-6,8H2,1-2H3,(H2,13,16,17)/t10-/m0/s1

> <INCHI_KEY>
HCRKCZRJWPKOAR-JTQLQIEISA-N

> <FORMULA>
C12H21N3O5S3

> <MOLECULAR_WEIGHT>
383.507

> <EXACT_MASS>
383.064332867

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
37.92896041973152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[3,2-e][1,2]thiazine-6-sulfonamide

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.674520266902024

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.194564077604486

> <JCHEM_PKA_STRONGEST_BASIC>
6.77741557633042

> <JCHEM_POLAR_SURFACE_AREA>
118.8

> <JCHEM_REFRACTIVITY>
87.1995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
brinzolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015325
     RDKit          3D
Brinzolamide
 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.6848    3.9984    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313    3.3307    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    1.9696    0.2388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    0.9645   -0.1373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1853    0.8896    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.3077   -0.2201 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008   -0.1374    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501    0.4421    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.1751   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1492   -1.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809   -1.8723   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660   -0.9514   -1.2467 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.6248   -0.5665   -2.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321   -2.1647   -1.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.3668   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -2.7421   -0.7300 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -2.0605   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9174   -2.8460    0.3586 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.6652   -3.4846   -1.0321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7901   -1.9353    1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5455   -4.0256    1.2506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214   -0.7532    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -0.3947   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.6447    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    5.0864    1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922    4.1129    0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030    3.8900    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    3.6092   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4018    1.8349    1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8259    1.1734   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038    0.2461    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2259   -2.9563   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696   -1.8659    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -1.5142   -0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5946   -3.0163   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -3.3638   -1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575   -0.0644    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 18 21  2  0
 17 22  2  0
 22 23  1  0
 23  4  1  0
 23 15  2  0
  1 24  1  0
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  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  6
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 19 42  1  0
 19 43  1  0
 22 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1194                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.082   2.798   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      13.873   2.497   0.000  0.00  0.00           S+0
HETATM    3  S   UNK     0      16.312   1.258   0.000  0.00  0.00           S+0
HETATM    4  O   UNK     0      11.852   4.132   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.312   4.132   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.414   2.028   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      16.312   2.798   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.312  -0.282   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       9.748   2.028   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      11.082  -1.822   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      17.852   1.258   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      11.082  -0.282   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748   0.488   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.416   0.488   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.416   2.028   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.415   2.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.873   0.019   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081   2.028   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.772   1.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.748  -2.592   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748   2.798   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.748  -4.132   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   2.798   0.000  0.00  0.00           C+0
CONECT    1    4    5    9   15                                             
CONECT    2   15   19                                                       
CONECT    3    7    8   11   19                                             
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6   21   23                                                       
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    1   13   16                                                  
CONECT   10   12   20                                                       
CONECT   11    3                                                            
CONECT   12   10   13   14                                                  
CONECT   13    9   12                                                       
CONECT   14   12   15   17                                                  
CONECT   15    1    2   14                                                  
CONECT   16    9   18                                                       
CONECT   17   14   19                                                       
CONECT   18   16   21                                                       
CONECT   19    2    3   17                                                  
CONECT   20   10   22                                                       
CONECT   21    6   18                                                       
CONECT   22   20                                                            
CONECT   23    6                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0015325
HETATM    1  C1  UNL     1      -0.685   3.998   0.874  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.731   3.331   0.057  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.994   1.970   0.239  1.00  0.00           N  
HETATM    4  C3  UNL     1      -1.104   0.964  -0.137  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.185   0.890   0.591  1.00  0.00           C  
HETATM    6  N2  UNL     1       1.254   0.308  -0.220  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.301  -0.137   0.653  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.650   0.442   0.408  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.183   0.175  -0.944  1.00  0.00           C  
HETATM   10  O1  UNL     1       4.331  -1.149  -1.224  1.00  0.00           O  
HETATM   11  C8  UNL     1       5.181  -1.872  -0.426  1.00  0.00           C  
HETATM   12  S1  UNL     1       0.666  -0.951  -1.247  1.00  0.00           S  
HETATM   13  O2  UNL     1       0.625  -0.566  -2.678  1.00  0.00           O  
HETATM   14  O3  UNL     1       1.532  -2.165  -1.099  1.00  0.00           O  
HETATM   15  C9  UNL     1      -0.993  -1.367  -0.755  1.00  0.00           C  
HETATM   16  S2  UNL     1      -1.977  -2.742  -0.730  1.00  0.00           S  
HETATM   17  C10 UNL     1      -3.378  -2.060  -0.026  1.00  0.00           C  
HETATM   18  S3  UNL     1      -4.917  -2.846   0.359  1.00  0.00           S  
HETATM   19  N3  UNL     1      -5.665  -3.485  -1.032  1.00  0.00           N  
HETATM   20  O4  UNL     1      -5.790  -1.935   1.143  1.00  0.00           O  
HETATM   21  O5  UNL     1      -4.545  -4.026   1.251  1.00  0.00           O  
HETATM   22  C11 UNL     1      -3.021  -0.753   0.169  1.00  0.00           C  
HETATM   23  C12 UNL     1      -1.782  -0.395  -0.211  1.00  0.00           C  
HETATM   24  H1  UNL     1      -0.574   3.645   1.909  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.019   5.086   1.009  1.00  0.00           H  
HETATM   26  H3  UNL     1       0.292   4.113   0.353  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.703   3.890   0.275  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.525   3.609  -1.018  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.402   1.835   1.215  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.826   1.173  -1.232  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.004   0.246   1.506  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.550   1.873   0.889  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.381  -1.265   0.552  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.998   0.005   1.728  1.00  0.00           H  
HETATM   35  H12 UNL     1       4.334   0.003   1.180  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.659   1.544   0.630  1.00  0.00           H  
HETATM   37  H14 UNL     1       3.509   0.676  -1.694  1.00  0.00           H  
HETATM   38  H15 UNL     1       5.162   0.720  -1.071  1.00  0.00           H  
HETATM   39  H16 UNL     1       5.226  -2.956  -0.770  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.770  -1.866   0.610  1.00  0.00           H  
HETATM   41  H18 UNL     1       6.213  -1.514  -0.444  1.00  0.00           H  
HETATM   42  H19 UNL     1      -6.595  -3.016  -1.214  1.00  0.00           H  
HETATM   43  H20 UNL     1      -5.020  -3.364  -1.848  1.00  0.00           H  
HETATM   44  H21 UNL     1      -3.758  -0.064   0.625  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29
CONECT    4    5   23   30
CONECT    5    6   31   32
CONECT    6    7   12
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11
CONECT   11   39   40   41
CONECT   12   13   13   14   14
CONECT   12   15
CONECT   15   16   23   23
CONECT   16   17
CONECT   17   18   22   22
CONECT   18   19   20   20   21
CONECT   18   21
CONECT   19   42   43
CONECT   22   23   44
END

HMDB0015325
     RDKit          3D
Brinzolamide
 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.6848    3.9984    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7313    3.3307    0.0572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9939    1.9696    0.2388 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1036    0.9645   -0.1373 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1853    0.8896    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542    0.3077   -0.2201 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3008   -0.1374    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6501    0.4421    0.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.1751   -0.9438 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3305   -1.1492   -1.2240 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809   -1.8723   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6660   -0.9514   -1.2467 S   0  0  0  0  0  6  0  0  0  0  0  0
    0.6248   -0.5665   -2.6775 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5321   -2.1647   -1.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.3668   -0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -2.7421   -0.7300 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3778   -2.0605   -0.0255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9174   -2.8460    0.3586 S   0  0  0  0  0  6  0  0  0  0  0  0
   -5.6652   -3.4846   -1.0321 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7901   -1.9353    1.1430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5455   -4.0256    1.2506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0214   -0.7532    0.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7824   -0.3947   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.6447    1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0187    5.0864    1.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2922    4.1129    0.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7030    3.8900    0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5255    3.6092   -1.0180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4018    1.8349    1.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8259    1.1734   -1.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038    0.2461    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5499    1.8730    0.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3810   -1.2649    0.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    0.0052    1.7275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3342    0.0026    1.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589    1.5444    0.6300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5087    0.6758   -1.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1616    0.7195   -1.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2259   -2.9563   -0.7705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7696   -1.8659    0.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2130   -1.5142   -0.4435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5946   -3.0163   -1.2137 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0198   -3.3638   -1.8485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7575   -0.0644    0.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  2  0
 12 14  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 18 21  2  0
 17 22  2  0
 22 23  1  0
 23  4  1  0
 23 15  2  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  6
  5 31  1  0
  5 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 19 42  1  0
 19 43  1  0
 22 44  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Azopt	ChEBI
Alcon brand OF brinzolamide	HMDB
Allphar brand OF brinzolamide	HMDB
(R)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno(3,2-e)-1,2-thiazine-6-sulfonamide 1,1-dioxide	HMDB

Chemical Formula

C₁₂H₂₁N₃O₅S₃

Average Molecular Weight

383.507

Monoisotopic Molecular Weight

383.064332867

IUPAC Name

(4R)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-2H,3H,4H-1λ⁶-thieno[3,2-e][1,2]thiazine-6-sulfonamide

Traditional Name

brinzolamide

CAS Registry Number

138890-62-7

SMILES

CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

InChI Identifier

InChI=1S/C12H21N3O5S3/c1-3-14-10-8-15(5-4-6-20-2)23(18,19)12-9(10)7-11(21-12)22(13,16)17/h7,10,14H,3-6,8H2,1-2H3,(H2,13,16,17)/t10-/m0/s1

InChI Key

HCRKCZRJWPKOAR-JTQLQIEISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one sulfur atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Thienothiazines

Sub Class

Not Available

Direct Parent

Thienothiazines

Alternative Parents

Substituents

Thienothiazine
2,3,5-trisubstituted thiophene
Aralkylamine
Ortho-thiazine
Organosulfonic acid amide
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Sulfonyl
Heteroaromatic compound
Aminosulfonyl compound
Thiophene
Dialkyl ether
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:41212 )
thienothiazine (CHEBI:41212 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015325)
Membrane (HMDB: HMDB0015325)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	131 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.71 g/L	Not Available
LogP	-1.8	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	-0.65	ALOGPS
logP	-0.67	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.19	ChemAxon
pKa (Strongest Basic)	6.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.8 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	87.2 m³·mol⁻¹	ChemAxon
Polarizability	37.93 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
DarkChem	[M+H]+	185.556	31661259
DarkChem	[M-H]-	178.798	31661259
DeepCCS	[M+H]+	183.676	30932474
DeepCCS	[M-H]-	181.318	30932474
DeepCCS	[M-2H]-	214.955	30932474
DeepCCS	[M+Na]+	190.962	30932474
AllCCS	[M+H]+	181.3	32859911
AllCCS	[M+H-H2O]+	178.8	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.3	32859911
AllCCS	[M-H]-	177.3	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	178.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brinzolamide	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O	4748.9	Standard polar	33892256
Brinzolamide	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O	3523.1	Standard non polar	33892256
Brinzolamide	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O	3261.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brinzolamide,1TMS,isomer #1	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2	3144.8	Semi standard non polar	33892256
Brinzolamide,1TMS,isomer #1	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2	3109.4	Standard non polar	33892256
Brinzolamide,1TMS,isomer #1	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2	4625.0	Standard polar	33892256
Brinzolamide,1TMS,isomer #2	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C	3055.4	Semi standard non polar	33892256
Brinzolamide,1TMS,isomer #2	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C	3201.6	Standard non polar	33892256
Brinzolamide,1TMS,isomer #2	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C	5402.1	Standard polar	33892256
Brinzolamide,2TMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C	3095.4	Semi standard non polar	33892256
Brinzolamide,2TMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C	3349.8	Standard non polar	33892256
Brinzolamide,2TMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C)S2)[Si](C)(C)C	4330.9	Standard polar	33892256
Brinzolamide,2TMS,isomer #2	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2	3082.3	Semi standard non polar	33892256
Brinzolamide,2TMS,isomer #2	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2	3296.2	Standard non polar	33892256
Brinzolamide,2TMS,isomer #2	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2	4428.2	Standard polar	33892256
Brinzolamide,3TMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C	3134.4	Semi standard non polar	33892256
Brinzolamide,3TMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C	3547.2	Standard non polar	33892256
Brinzolamide,3TMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)S2)[Si](C)(C)C	4160.3	Standard polar	33892256
Brinzolamide,1TBDMS,isomer #1	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2	3361.8	Semi standard non polar	33892256
Brinzolamide,1TBDMS,isomer #1	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2	3378.0	Standard non polar	33892256
Brinzolamide,1TBDMS,isomer #1	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2	4622.3	Standard polar	33892256
Brinzolamide,1TBDMS,isomer #2	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C	3282.7	Semi standard non polar	33892256
Brinzolamide,1TBDMS,isomer #2	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C	3432.5	Standard non polar	33892256
Brinzolamide,1TBDMS,isomer #2	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2)[Si](C)(C)C(C)(C)C	5398.1	Standard polar	33892256
Brinzolamide,2TBDMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3518.9	Semi standard non polar	33892256
Brinzolamide,2TBDMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3859.0	Standard non polar	33892256
Brinzolamide,2TBDMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	4329.9	Standard polar	33892256
Brinzolamide,2TBDMS,isomer #2	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2	3575.5	Semi standard non polar	33892256
Brinzolamide,2TBDMS,isomer #2	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2	3795.1	Standard non polar	33892256
Brinzolamide,2TBDMS,isomer #2	CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2	4408.5	Standard polar	33892256
Brinzolamide,3TBDMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	3794.5	Semi standard non polar	33892256
Brinzolamide,3TBDMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	4287.5	Standard non polar	33892256
Brinzolamide,3TBDMS,isomer #1	CCN([C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)S2)[Si](C)(C)C(C)(C)C	4200.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brinzolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-9363000000-c2ce0727d8312538cab4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brinzolamide 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Brinzolamide LC-ESI-qTof , Positive-QTOF	splash10-000i-3940000000-29878662225bb11586ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Brinzolamide , positive-QTOF	splash10-000i-3940000000-29878662225bb11586ed	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 10V, Positive-QTOF	splash10-00sr-2019000000-988ac9cefa8fb23facba	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 20V, Positive-QTOF	splash10-0fk9-3690000000-c40760f0b6f44cc24c8e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 40V, Positive-QTOF	splash10-00dl-9100000000-f485ec4bc8d717b8b51b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 10V, Negative-QTOF	splash10-017i-6893000000-c3e14fd7fd97db235170	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 20V, Negative-QTOF	splash10-0fb9-7189000000-719789413373ebe82904	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 40V, Negative-QTOF	splash10-004i-9010000000-929e6fe33dd2964ee558	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 10V, Positive-QTOF	splash10-001i-0009000000-3c94e44f36675ba706e3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 20V, Positive-QTOF	splash10-001i-0009000000-986efaaf32a24d0fac0f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 40V, Positive-QTOF	splash10-00lr-0091000000-e7907c2f053f25cc9921	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 10V, Negative-QTOF	splash10-001i-0009000000-de46e421dd0efb4be9dd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 20V, Negative-QTOF	splash10-003r-3119000000-aafd05e736363b690ad1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brinzolamide 40V, Negative-QTOF	splash10-06vi-9378000000-faad917334f371082bf7	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB01194	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01194	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01194

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

62077

KEGG Compound ID

C07760

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Brinzolamide

METLIN ID

Not Available

PubChem Compound

68844

PDB ID

BZ1

ChEBI ID

3176

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

DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. [PubMed:10665514 ]
Iester M: Brinzolamide ophthalmic suspension: a review of its pharmacology and use in the treatment of open angle glaucoma and ocular hypertension. Clin Ophthalmol. 2008 Sep;2(3):517-23. [PubMed:19668749 ]
Kaup M, Plange N, Niegel M, Remky A, Arend O: Effects of brinzolamide on ocular haemodynamics in healthy volunteers. Br J Ophthalmol. 2004 Feb;88(2):257-62. [PubMed:14736787 ]
Ermis SS, Ozturk F, Inan UU: Comparing the effects of travoprost and brinzolamide on intraocular pressure after phacoemulsification. Eye (Lond). 2005 Mar;19(3):303-7. [PubMed:15258611 ]
Iester M, Altieri M, Michelson G, Vittone P, Traverso CE, Calabria G: Retinal peripapillary blood flow before and after topical brinzolamide. Ophthalmologica. 2004 Nov-Dec;218(6):390-6. [PubMed:15564757 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. 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

Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [PubMed:14684332 ]
Herkel U, Pfeiffer N: Update on topical carbonic anhydrase inhibitors. Curr Opin Ophthalmol. 2001 Apr;12(2):88-93. [PubMed:11224713 ]

Enzyme Details

3. 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

Stams T, Chen Y, Boriack-Sjodin PA, Hurt JD, Liao J, May JA, Dean T, Laipis P, Silverman DN, Christianson DW: Structures of murine carbonic anhydrase IV and human carbonic anhydrase II complexed with brinzolamide: molecular basis of isozyme-drug discrimination. Protein Sci. 1998 Mar;7(3):556-63. [PubMed:9541386 ]
DeSantis L: Preclinical overview of brinzolamide. Surv Ophthalmol. 2000 Jan;44 Suppl 2:S119-29. [PubMed:10665514 ]
Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [PubMed:14684332 ]
Boriack-Sjodin PA, Zeitlin S, Chen HH, Crenshaw L, Gross S, Dantanarayana A, Delgado P, May JA, Dean T, Christianson DW: Structural analysis of inhibitor binding to human carbonic anhydrase II. Protein Sci. 1998 Dec;7(12):2483-9. [PubMed:9865942 ]
Ilies M, Supuran CT, Scozzafava A, Casini A, Mincione F, Menabuoni L, Caproiu MT, Maganu M, Banciu MD: Carbonic anhydrase inhibitors: sulfonamides incorporating furan-, thiophene- and pyrrole-carboxamido groups possess strong topical intraocular pressure lowering properties as aqueous suspensions. Bioorg Med Chem. 2000 Aug;8(8):2145-55. [PubMed:11003159 ]
Iester M: Brinzolamide ophthalmic suspension: a review of its pharmacology and use in the treatment of open angle glaucoma and ocular hypertension. Clin Ophthalmol. 2008 Sep;2(3):517-23. [PubMed:19668749 ]
Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [PubMed:14971907 ]

Enzyme Details

4. Carbonic anhydrase 5A, mitochondrial

General function:: Involved in carbonate dehydratase activity
Specific function:: Reversible hydration of carbon dioxide. Low activity.
Gene Name:: CA5A
Uniprot ID:: P35218
Molecular weight:: 34750.21

References

Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [PubMed:14971907 ]

Enzyme Details

5. 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

Vullo D, Franchi M, Gallori E, Antel J, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Inhibition of mitochondrial isozyme V with aromatic and heterocyclic sulfonamides. J Med Chem. 2004 Feb 26;47(5):1272-9. [PubMed:14971907 ]

Showing metabocard for Brinzolamide (HMDB0015325)

MOL for HMDB0015325 (Brinzolamide)

3D MOL for HMDB0015325 (Brinzolamide)

3D SDF for HMDB0015325 (Brinzolamide)

3D-SDF for HMDB0015325 (Brinzolamide)

PDB for HMDB0015325 (Brinzolamide)

3D PDB for HMDB0015325 (Brinzolamide)

SMILES for HMDB0015325 (Brinzolamide)

INCHI for HMDB0015325 (Brinzolamide)

Structure for HMDB0015325 (Brinzolamide)

3D Structure for HMDB0015325 (Brinzolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References

References

References