Tizanidine (CHEM002250)

Record Information
Version1.0
Creation Date2009-07-21 20:27:26 UTC
Update Date2026-05-14 16:46:22 UTC
Accession NumberCHEM002250
Identification
Common NameTizanidine
ClassSmall Molecule
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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Adrenergic alpha-2 Receptor Agonist
  • Adrenergic alpha-Agonist
  • Amide
  • Amine
  • Analgesic
  • Anticonvulsant
  • Drug
  • Metabolite
  • Muscle Relaxant
  • Muscle Relaxant, Central
  • Muscle Relaxant, Skeletal
  • Neuromuscular Agent
  • Organic Compound
  • Organochloride
  • Parasympatholytic
  • Synthetic Compound
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazoleChEBI
TizanidinaChEBI
TizanidinumChEBI
SirdaludKegg
5-Chloro-4-(2-imidazolin-4-on-2-ylamino)-2,1,3-benzothiadiazoleHMDB
ZanaflexHMDB
Tizanidine monohydrochlorideHMDB
5-Chloro-4-(2-imidazolin-2-yl-amino)-2,1,3-benzothiadiazoleHMDB
Acorda brand OF tizanidine hydrochlorideHMDB
Novartis brand OF tizanidine hydrochlorideHMDB
Sanofi synthelabo brand OF tizanidine hydrochlorideHMDB
Tizanidine hydrochlorideHMDB
Chemical FormulaC9H8ClN5S
Average Molecular Mass253.711 g/mol
Monoisotopic Mass253.019 g/mol
CAS Registry Number51322-75-9
IUPAC Name5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
Traditional Nametizanidine
SMILESClC1=C(NC2=NCCN2)C2=NSN=C2C=C1
InChI IdentifierInChI=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 KeyXFYDIVBRZNQMJC-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiadiazoles
Sub ClassNot Available
Direct ParentBenzothiadiazoles
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1.33e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.6ALOGPS
logP2.02ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)7.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.2 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.77 m³·mol⁻¹ChemAxon
Polarizability23.97 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityTizanidine reduces spasticity by increasing presynaptic inhibition of motor neurons through agonist action at a2-adrenergic receptor sites.
Metabolism Route of Elimination: Approximately 95% of an administered dose is metabolized. Half Life: 2.5 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of increased muscle tone associated with spasticity
Minimum Risk LevelNot Available
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
SymptomsNot Available
TreatmentShould overdose occur, basic steps to ensure the adequacy of an airway and the monitoring of cardiovascular and respiratory systems should be undertaken. In general, symptoms resolve within one to three days following discontinuation of tizanidine and administration of appropriate therapy. Due to the similar mechanism of action, symptoms and management of tizanidine overdose are similar to those following clonidine overdose. (2)
Concentrations
Not Available
External Links
DrugBank IDDB00697
HMDB IDHMDB0014835
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTizanidine
Chemspider ID5287
ChEBI ID63629
PubChem Compound ID5487
Kegg Compound IDC07452
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Pavel Hradil, Lubomir Kvapil, Martin Grepl, Jan Novotny, “METHOD FOR THE PREPARATION OF TIZANIDINE HYDROCHLORIDE.” U.S. Patent US20110263863, issued October 27, 2011.

MSDSNot Available
General References
1. 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.
2. 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.
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21317414
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21733633
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21982341
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22196407
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22223284