Jump To Section:

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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014835

Secondary Accession Numbers

HMDB14835

Metabolite Identification

Common Name

Tizanidine

Description

Tizanidine is a short-acting drug for the management of spasticity. Tizanidine is an agonist at a2-adrenergic receptor sites and presumably reduces spasticity by increasing presynaptic inhibition of motor neurons. In animal models, tizanidine has no direct effect on skeletal muscle fibers or the neuromuscular junction, and no major effect on monosynaptic spinal reflexes. The effects of tizanidine are greatest on polysynaptic pathways. The overall effect of these actions is thought to reduce facilitation of spinal motor neurons. Tizanidine has two major metabolites: (1) 5-chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiazdiazole and (2) 5-chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiadiazole (PMID: 9929503 , 19961320 ).

Structure

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


  Mrv1652305271920112D          

 16 18  0  0  0  0            999 V2000
    2.2413   -0.3751    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.6469   -1.2002    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8695    1.6829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.4499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2021    0.5269    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -0.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1654   -1.8640    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    1.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558    0.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -0.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -1.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -0.7876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703   -2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9558   -1.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  2  6  1  0  0  0  0
  2  7  1  0  0  0  0
  3  8  1  0  0  0  0
  3 10  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014835

> <DATABASE_NAME>
hmdb

> <SMILES>
ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H8ClN5S/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9/h1-2H,3-4H2,(H2,11,12,13)

> <INCHI_KEY>
XFYDIVBRZNQMJC-UHFFFAOYSA-N

> <FORMULA>
C9H8ClN5S

> <MOLECULAR_WEIGHT>
253.711

> <EXACT_MASS>
253.018893678

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
23.96797413243427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
2.0246730729999998

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.494660778520407

> <JCHEM_POLAR_SURFACE_AREA>
62.2

> <JCHEM_REFRACTIVITY>
64.7664

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tizanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1 Cl   UNK     0       4.184  -0.700   0.000  0.00  0.00          Cl+0
HETATM    2  S   UNK     0      10.541  -2.240   0.000  0.00  0.00           S+0
HETATM    3  N   UNK     0       5.356   3.141   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       6.851   0.840   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.111   0.984   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.642  -1.001   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.642  -3.479   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.850   3.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080   2.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.517   1.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.851  -0.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.185  -1.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.185  -3.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.517  -1.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.851  -3.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.517  -3.010   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2    6    7                                                       
CONECT    3    8   10                                                       
CONECT    4   10   11                                                       
CONECT    5    9   10                                                       
CONECT    6    2   12                                                       
CONECT    7    2   13                                                       
CONECT    8    3    9                                                       
CONECT    9    5    8                                                       
CONECT   10    3    4    5                                                  
CONECT   11    4   12   14                                                  
CONECT   12    6   11   13                                                  
CONECT   13    7   12   15                                                  
CONECT   14    1   11   16                                                  
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole	ChEBI
Tizanidina	ChEBI
Tizanidinum	ChEBI
Sirdalud	Kegg
5-Chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiadiazole	HMDB
Zanaflex	HMDB
Tizanidine monohydrochloride	HMDB
5-Chloro-4-(2-imidazolin-2-yl-amino)-2,1,3-benzothiadiazole	HMDB
Acorda brand OF tizanidine hydrochloride	HMDB
Novartis brand OF tizanidine hydrochloride	HMDB
Sanofi synthelabo brand OF tizanidine hydrochloride	HMDB
Tizanidine hydrochloride	HMDB

Chemical Formula

C₉H₈ClN₅S

Average Molecular Weight

253.711

Monoisotopic Molecular Weight

253.018893678

IUPAC Name

5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine

Traditional Name

tizanidine

CAS Registry Number

51322-75-9

SMILES

ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1

InChI Identifier

InChI=1S/C9H8ClN5S/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9/h1-2H,3-4H2,(H2,11,12,13)

InChI Key

XFYDIVBRZNQMJC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzothiadiazoles. These are heterocyclic aromatic compounds containing a benzene ring fused to a thiadiazole ring. Thiadiazole is a five-membered aromatic heterocycle made up of one sulfur atom and two nitrogen atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiadiazoles

Sub Class

Not Available

Direct Parent

Benzothiadiazoles

Alternative Parents

Substituents

2,1,3-benzothiadiazole
Aryl chloride
Aryl halide
Benzenoid
Azole
Heteroaromatic compound
2-imidazoline
Thiadiazole
Guanidine
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Carboximidamide
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoles (CHEBI:63629 )
benzothiadiazole (CHEBI:63629 )

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

Membrane (HMDB: HMDB0014835)

Source

Exogenous

Exogenous (HMDB: HMDB0014835)

Process

Not Available

Role

Industrial application

Alpha-adrenergic agonist (HMDB: HMDB0014835)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Muscle relaxant (HMDB: HMDB0014835)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.13 g/L	Not Available
LogP	1.4	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	149.4	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	1.6	ALOGPS
logP	2.02	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	7.49	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.2 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.77 m³·mol⁻¹	ChemAxon
Polarizability	23.97 Å³	ChemAxon
Number of Rings	3	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]+	147.371	30932474
DeepCCS	[M-H]-	144.976	30932474
DeepCCS	[M-2H]-	178.449	30932474
DeepCCS	[M+Na]+	153.414	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	150.5	32859911
AllCCS	[M+Na-2H]-	150.2	32859911
AllCCS	[M+HCOO]-	150.1	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.	2.26 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3005 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	120.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	963.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	309.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	88.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	74.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	290.0 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	342.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	454.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	703.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	238.6 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	950.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	215.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	557.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	338.4 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	160.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tizanidine	ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1	3476.4	Standard polar	33892256
Tizanidine	ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1	2408.8	Standard non polar	33892256
Tizanidine	ClC1=C(NC2=NCCN2)C2=NSN=C2C=C1	2471.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tizanidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=C(Cl)C=CC2=NSN=C12	2587.9	Semi standard non polar	33892256
Tizanidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=C(Cl)C=CC2=NSN=C12	2368.1	Standard non polar	33892256
Tizanidine,1TMS,isomer #1	C[Si](C)(C)N(C1=NCCN1)C1=C(Cl)C=CC2=NSN=C12	4814.6	Standard polar	33892256
Tizanidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=C(Cl)C=CC2=NSN=C12	2622.0	Semi standard non polar	33892256
Tizanidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=C(Cl)C=CC2=NSN=C12	2484.5	Standard non polar	33892256
Tizanidine,1TMS,isomer #2	C[Si](C)(C)N1CCN=C1NC1=C(Cl)C=CC2=NSN=C12	4332.7	Standard polar	33892256
Tizanidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=C(Cl)C=CC2=NSN=C12)[Si](C)(C)C	2544.4	Semi standard non polar	33892256
Tizanidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=C(Cl)C=CC2=NSN=C12)[Si](C)(C)C	2469.1	Standard non polar	33892256
Tizanidine,2TMS,isomer #1	C[Si](C)(C)N1CCN=C1N(C1=C(Cl)C=CC2=NSN=C12)[Si](C)(C)C	3869.1	Standard polar	33892256
Tizanidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=C(Cl)C=CC2=NSN=C12	2774.6	Semi standard non polar	33892256
Tizanidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=C(Cl)C=CC2=NSN=C12	2604.1	Standard non polar	33892256
Tizanidine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=NCCN1)C1=C(Cl)C=CC2=NSN=C12	4806.4	Standard polar	33892256
Tizanidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=C(Cl)C=CC2=NSN=C12	2849.4	Semi standard non polar	33892256
Tizanidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=C(Cl)C=CC2=NSN=C12	2697.3	Standard non polar	33892256
Tizanidine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCN=C1NC1=C(Cl)C=CC2=NSN=C12	4456.0	Standard polar	33892256
Tizanidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=C(Cl)C=CC2=NSN=C12)[Si](C)(C)C(C)(C)C	2898.4	Semi standard non polar	33892256
Tizanidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=C(Cl)C=CC2=NSN=C12)[Si](C)(C)C(C)(C)C	2909.8	Standard non polar	33892256
Tizanidine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCN=C1N(C1=C(Cl)C=CC2=NSN=C12)[Si](C)(C)C(C)(C)C	3853.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tizanidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3960000000-3aca4c577af73cfa3997	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tizanidine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-5490000000-5ee0610f321160b63c82	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 10V, Positive-QTOF	splash10-0udi-0090000000-03af7132e7796b671fd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 20V, Positive-QTOF	splash10-0udi-2090000000-6ed6a84b177d1e4425ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 40V, Positive-QTOF	splash10-014i-9020000000-a1d6e32b00fde6ba39d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 10V, Negative-QTOF	splash10-0udi-0090000000-9ebe0248119b57c01175	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 20V, Negative-QTOF	splash10-0udi-1390000000-5ba6bc72d04cb138d433	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 40V, Negative-QTOF	splash10-0a4i-2590000000-0e6b317aeab569aa3c97	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 10V, Positive-QTOF	splash10-0udi-0090000000-81fa3242a4171a3e23e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 20V, Positive-QTOF	splash10-0udi-0090000000-81fa3242a4171a3e23e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 40V, Positive-QTOF	splash10-000l-0930000000-89d08fc212d90d4e75ee	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 10V, Negative-QTOF	splash10-0udi-0090000000-809deeeabd14377046e0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 20V, Negative-QTOF	splash10-001i-9000000000-c2fa753da65a4bac80a1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tizanidine 40V, Negative-QTOF	splash10-001i-9000000000-a9ed1a171086d3aff472	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00697	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00697	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00697

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5287

KEGG Compound ID

C07452

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tizanidine

METLIN ID

Not Available

PubChem Compound

5487

PDB ID

Not Available

ChEBI ID

63629

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

Shellenberger MK, Groves L, Shah J, Novack GD: A controlled pharmacokinetic evaluation of tizanidine and baclofen at steady state. Drug Metab Dispos. 1999 Feb;27(2):201-4. [PubMed:9929503 ]
Zhou SF, Wang B, Yang LP, Liu JP: Structure, function, regulation and polymorphism and the clinical significance of human cytochrome P450 1A2. Drug Metab Rev. 2010 May;42(2):268-354. doi: 10.3109/03602530903286476. [PubMed:19961320 ]

Enzymes

Enzyme Details

1. Cytochrome P450 1A2

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423 ]
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 ]
Shellenberger MK, Groves L, Shah J, Novack GD: A controlled pharmacokinetic evaluation of tizanidine and baclofen at steady state. Drug Metab Dispos. 1999 Feb;27(2):201-4. [PubMed:9929503 ]

Enzyme Details

2. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]

Enzyme Details

3. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

References

Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]

Enzyme Details

4. Alpha-2C adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins
Gene Name:: ADRA2C
Uniprot ID:: P18825
Molecular weight:: 49521.6

References

Piletz JE, Zhu H, Chikkala DN: Comparison of ligand binding affinities at human I1-imidazoline binding sites and the high affinity state of alpha-2 adrenoceptor subtypes. J Pharmacol Exp Ther. 1996 Nov;279(2):694-702. [PubMed:8930173 ]

Showing metabocard for Tizanidine (HMDB0014835)

MOL for HMDB0014835 (Tizanidine)

3D MOL for HMDB0014835 (Tizanidine)

3D SDF for HMDB0014835 (Tizanidine)

3D-SDF for HMDB0014835 (Tizanidine)

PDB for HMDB0014835 (Tizanidine)

3D PDB for HMDB0014835 (Tizanidine)

SMILES for HMDB0014835 (Tizanidine)

INCHI for HMDB0014835 (Tizanidine)

Structure for HMDB0014835 (Tizanidine)

3D Structure for HMDB0014835 (Tizanidine)

Experimental Collision Cross Sections

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