Tizanidine (CED0005478)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:26 UTC

Update Date

2026-05-14 16:46:22 UTC

SynCED ID

CED0005478

Secondary Accession Numbers

CHEM002250
T3D2862

Identification

Common Name

Tizanidine

Class

Small Molecule

Description

Tizanidine is an exogenous organic compound with the formula C9H8ClN5S and an average molecular weight of 253.71 g/mol. It exists as a solid at room temperature. Tizanidine belongs to the benzothiadiazoles, a class of organoheterocyclic compounds within the organic compounds. Used as a muscle relaxant and an alpha-adrenergic agonist, tizanidine is recorded in healthcare, pharmaceuticals, and veterinary products. It is also found in electrical and electronic equipment, specifically electrically stimulated smoking devices, as well as household cleaning and consumer products such as tobacco smoke filters and non-electric simulated smoking devices. The recorded exposure route for this compound is oral. Tizanidine interacts with seven recorded protein targets. It acts as an agonist of the alpha-2B adrenergic receptor (ADRA2B), alpha-2C adrenergic receptor (ADRA2C), nischarin (NISCH), and alpha-1D adrenergic receptor (ADRA1D), among two other proteins. Specifically, tizanidine reduces spasticity by increasing presynaptic inhibition of motor neurons through agonist action at alpha-2A adrenergic receptor (ADRA2A) sites.

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

MOL SDF PDB SMILES InChI

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 Mass

253.711 g/mol

Monoisotopic Mass

253.019 g/mol

CAS Registry Number

51322-75-9

IUPAC Name

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

Traditional Name

tizanidine

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

alpha-adrenergic agonist ?

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.33e-01 g/L

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4i-3960000000-3aca4c577af73cfa3997	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-03af7132e7796b671fd2	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2090000000-6ed6a84b177d1e4425ad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-014i-9020000000-a1d6e32b00fde6ba39d4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-9ebe0248119b57c01175	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1390000000-5ba6bc72d04cb138d433	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2590000000-0e6b317aeab569aa3c97	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-81fa3242a4171a3e23e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-81fa3242a4171a3e23e8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000l-0930000000-89d08fc212d90d4e75ee	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0090000000-809deeeabd14377046e0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9000000000-c2fa753da65a4bac80a1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9000000000-a9ed1a171086d3aff472	Not Available	View Spectrum
MS	MS Spectrum	splash10-0udi-5490000000-5ee0610f321160b63c82	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
705.0 Log mg/kg [400:1300]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Tizanidine reduces spasticity by increasing presynaptic inhibition of motor neurons through agonist action at a2-adrenergic receptor sites.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Should 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)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000365	Muscle relaxants?Muscle relaxants are synthetic chemicals primarily used to alleviate muscle spasms and discomfort by acting on the central nervous system or peripheral neuromuscular junctions.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000617	Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000618	Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000741	Pigment Pastes?Pigment pastes are concentrated dispersions of pigments used to impart color and properties to materials.	Paper, pulp & fiber products	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Tizanidine

Tizanidine Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Known	Not Available
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	Prediction Confidence Score 0.608 Applicability Domain 1.0 Statistical Significance 4.10e-04 Supporting Reference Compounds 487 E-value 3.19182
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.608 Applicability Domain 1.0 Statistical Significance 3.10e-04 Supporting Reference Compounds 386 E-value 2.41333
Click to view 3D structure	Nischarin	Q9Y2I1	Humans	Predicted (SEA)	Prediction Confidence Score 0.493 Applicability Domain 1.0 Statistical Significance 8.00e-05 Supporting Reference Compounds 37 E-value 0.622794
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.49 Applicability Domain 0.585 Statistical Significance 9.60e-04 Supporting Reference Compounds 340 E-value 7.47353
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	Prediction Confidence Score 0.49 Applicability Domain 0.585 Statistical Significance 0.0025 Supporting Reference Compounds 376 E-value 19.8516
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	Prediction Confidence Score 0.49 Applicability Domain 0.585 Statistical Significance 0.0011 Supporting Reference Compounds 258 E-value 8.79696
Click to view 3D structure	Alpha-1A adrenergic receptor	P18130	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.49 Applicability Domain 1.0 Statistical Significance 4.00e-04 Supporting Reference Compounds 85 E-value 3.11397
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	Prediction Confidence Score 0.465 Applicability Domain 0.585 Statistical Significance 0.0022 Supporting Reference Compounds 298 E-value 17.1268
Click to view 3D structure	Alpha-1B adrenergic receptor	G3HDX1	Cricetulus griseus	Predicted (SEA)	Prediction Confidence Score 0.433 Applicability Domain 1.0 Statistical Significance 2.00e-05 Supporting Reference Compounds 5 E-value 0.155698
Click to view 3D structure	Alpha-2B adrenergic receptor	P19328	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.397 Applicability Domain 0.585 Statistical Significance 1.20e-04 Supporting Reference Compounds 30 E-value 0.934191
Click to view 3D structure	Nischarin	Q4G017	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.354 Applicability Domain 0.585 Statistical Significance 4.60e-04 Supporting Reference Compounds 18 E-value 3.58106
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P19327	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.345 Applicability Domain 0.585 Statistical Significance 0.0246 Supporting Reference Compounds 541 E-value 191.743
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	Prediction Confidence Score 0.323 Applicability Domain 0.571 Statistical Significance 0.0318 Supporting Reference Compounds 565 E-value 247.561
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.32 Applicability Domain 0.585 Statistical Significance 0.0156 Supporting Reference Compounds 208 E-value 121.523
Click to view 3D structure	Alpha-2A adrenergic receptor	Q28838	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.308 Applicability Domain 0.585 Statistical Significance 0.0016 Supporting Reference Compounds 32 E-value 12.4559
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	Prediction Confidence Score 0.3 Applicability Domain 0.571 Statistical Significance 0.0342 Supporting Reference Compounds 308 E-value 266.478
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.297 Applicability Domain 0.585 Statistical Significance 0.0767 Supporting Reference Compounds 953 E-value 597.026
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	Prediction Confidence Score 0.276 Applicability Domain 0.571 Statistical Significance 0.1249 Supporting Reference Compounds 823 E-value 972.648
Click to view 3D structure	Alpha-1B adrenergic receptor	P15823	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.272 Applicability Domain 0.585 Statistical Significance 0.0265 Supporting Reference Compounds 130 E-value 206.3
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	Prediction Confidence Score 0.264 Applicability Domain 0.571 Statistical Significance 0.1999 Supporting Reference Compounds 955 E-value 1556.21
Click to view 3D structure	Alpha-2A adrenergic receptor	P22909	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.261 Applicability Domain 0.585 Statistical Significance 0.0176 Supporting Reference Compounds 42 E-value 136.781
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.218 Applicability Domain 0.344 Statistical Significance 0.5155 Supporting Reference Compounds 593 E-value 4013.21
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.216 Applicability Domain 0.37 Statistical Significance 0.8734 Supporting Reference Compounds 1498 E-value 6799.58
Click to view 3D structure	Solute carrier family 22 member 1	O15245	Humans	Predicted (SEA)	Prediction Confidence Score 0.214 Applicability Domain 0.585 Statistical Significance 0.0157 Supporting Reference Compounds 30 E-value 122.223
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	Prediction Confidence Score 0.213 Applicability Domain 0.231 Low confidence Statistical Significance 0.4569 Supporting Reference Compounds 365 E-value 3556.93
Click to view 3D structure	Nischarin	Q9Y2I1	Humans	Known	Not Available
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Known	Tizanidine reduces spasticity by increasing presynaptic inhibition of motor neurons through agonist action at a2-adrenergic receptor sites.
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Known	Not Available
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00697

HMDB ID

HMDB0014835

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Not Available

General References

Drugs.com http://www.drugs.com/cons/Tizanidine.html
RxList: The Internet Drug Index (2009). http://www.rxlist.com/

Tizanidine (CED0005478)

Structure for CHEM002250: Tizanidine

Structure