Tizanidine

Identification

Name

Tizanidine

Accession Number

DB00697  (APRD00128)

Type

Small Molecule

Groups

Approved, Investigational

Description

Tizanidine is a fast-acting drug used for the management of muscle spasm, which may result from the effects of multiple sclerosis, stroke, an acquired brain injury, or a spinal cord injury ⁹. It may also be caused by musculoskeletal injury ⁵. Regardless of the cause, muscle spasticity can be an extremely painful and debilitating condition.

Initially approved by the FDA in 1996, tizanidine is an Alpha-2 adrenergic receptor agonist reducing spasticity by the presynaptic inhibition of excitatory neurotransmitters that cause firing of neurons promoting muscle spasm ^Label.

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Tizanidine (DB00697)

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Synonyms

• 5-Chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole
• Tizanidin
• Tizanidina
• Tizanidine
• Tizanidinum

External IDs

AN 021 / DS 103-282

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Tizanidine hydrochloride	B53E3NMY5C	64461-82-1	ZWUKMNZJRDGCTQ-UHFFFAOYSA-N

Product Images

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Tizanidine	Tablet	4 mg	Oral	Aa Pharma Inc	2004-11-17	Not applicable
Tizanidine	Tablet	2 mg	Oral	Aa Pharma Inc	Not applicable	Not applicable
Tizanidine Hydrochloride	Capsule, gelatin coated	6 mg/1	Oral	Actavis Pharma, Inc.	2012-02-06	Not applicable
Tizanidine Hydrochloride	Capsule, gelatin coated	4 mg/1	Oral	Actavis Pharma, Inc.	2012-02-06	Not applicable
Tizanidine Hydrochloride	Capsule, gelatin coated	2 mg/1	Oral	Actavis Pharma, Inc.	2012-02-06	Not applicable
Tizanidine Hydrochloride	Capsule, gelatin coated	2 mg/1	Oral	Clinical Solutions Wholsesale	2012-02-06	2017-06-21
Tizanidine Hydrochloride	Capsule, gelatin coated	6 mg/1	Oral	Lake Erie Medical DBA Quality Care Products LLC	2012-02-06	Not applicable
Tizanidine Hydrochloride	Capsule, gelatin coated	6 mg/1	Oral	bryant ranch prepack	2012-02-06	Not applicable
Zanaflex	Capsule	4 mg/1	Oral	Acorda Therapeutics, Inc.	2005-04-04	2019-07-31
Zanaflex	Capsule	4 mg/1	Oral	Stat Rx USA	2002-08-29	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Comfort Pac with Tizanidine	Kit	4 mg/1	Topical	Pd Rx Pharmaceuticals, Inc.	2013-07-09	Not applicable
Mylan-tizanidine	Tablet		Oral	Mylan Pharmaceuticals	2006-02-16	2017-01-09
Pal-tizanidine	Tablet		Oral	Paladin Labs Inc	1999-10-29	Not applicable
Tizandine	Tablet	2 mg/1	Oral	Direct Rx	2020-01-08	Not applicable
Tizanidine	Tablet	4 mg/1	Oral	Proficient Rx LP	2002-07-03	Not applicable
Tizanidine	Tablet	4 mg/1	Oral	St. Mary's Medical Park Pharmacy	2018-07-19	Not applicable
Tizanidine	Tablet	4 mg/1	Oral	REMEDYREPACK INC.	2018-10-26	Not applicable
Tizanidine	Tablet	4 mg/1	Oral	Cardinal Health	2002-07-03	2012-10-31
Tizanidine	Tablet	2 mg/1	Oral	St. Mary's Medical Park Pharmacy	2004-01-16	Not applicable
Tizanidine	Tablet	4 mg/1	Oral	Direct_Rx	2019-09-30	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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International/Other Brands

Cimbrar (Euroetika) / Musant (Actavis) / Myores (Meprofarm) / Navizan (Caber) / Relaxkov (Blaskov) / Sirdalid (Novartis) / Sirdalud (Novartis) / Sirdalud MR (Novartis) / Sizolan (Dr. Reddy's) / Spaslax (Panion & BF) / Telzanine (Nisshin Seiyaku) / Ternelin (Novartis) / Tizadin (ACL) / Tizaflex (Actavis) / Tizalud (Opsonin) / Tizan (Sun) / Zanpeak (Tatsumi Kagaku) / Zitanid (Novell)

Categories

• Adrenergic Agents
• Adrenergic Agonists
• Adrenergic alpha-2 Receptor Agonists
• Adrenergic alpha-Agonists
• Agents producing tachycardia
• Analgesics
• Anticonvulsants
• Autonomic Agents
• Bradycardia-Causing Agents
• Central alpha-2 Adrenergic Agonist
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP1A2 Substrates
• Cytochrome P-450 CYP1A2 Substrates with a Narrow Therapeutic Index
• Cytochrome P-450 Substrates
• Hypotensive Agents
• Imidazoles
• Imidazolines
• Muscle Relaxants
• Muscle Relaxants, Centrally Acting Agents
• Musculo-Skeletal System
• Neuromuscular Agents
• Neurotransmitter Agents
• Potential QTc-Prolonging Agents
• QTc Prolonging Agents
• Sensory System Agents

UNII

6AI06C00GW

CAS number

51322-75-9

Weight

Average: 253.711
Monoisotopic: 253.018893678

Chemical Formula

C₉H₈ClN₅S

InChI Key

XFYDIVBRZNQMJC-UHFFFAOYSA-N

InChI

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)

IUPAC Name

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

SMILES

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

Pharmacology

Indication

Tizanidine is indicated for the relief of muscle spasticity, which can interfere with daily activities. The general recommendation is to reserve tizanidine use for periods of time when there is a particular need for relief, as it has a short duration of action ^Label,11.

Associated Conditions

• Acute Low Back Pain
• Drug Withdrawal Headache
• Insomnia
• Migraine
• Seizures
• Spasticity, Muscle

Associated Therapies

• Withdrawal From Addictive Substance; Detoxification

Pharmacodynamics

A note on spasticity

Spasticity is an increase in muscle accompanied by uncontrolled, repetitive contractions of skeletal muscles which are involuntary. The patient suffering from muscle spasticity may have reduced mobility and high levels of pain, contributing to poor quality of life and problems performing activities of personal hygiene and care ⁷.

General effects

Tizanidine is a rapidly acting drug used for the relief of muscle spasticity when it is required for performing specific activities. It acts as an agonist at Alpha-2 adrenergic receptor sites and relieves symptoms of muscle spasticity, allowing the continuation of normal daily activities. In animal models, tizanidine has not been shown to exert direct effects on skeletal muscle fibers or the neuromuscular junction, and has shown no significant effect on monosynaptic spinal reflexes (consisting of the communication between only 1 sensory neuron and 1 motor neuron) ¹⁰. The frequency of muscle spasm and clonus are shown to be decreased by tizanidine ⁹. Tizanidine shows a stronger action on polysynaptic reflexes, which involve several interneurons (relay neurons) communicating with motor neurons stimulating muscle movement ¹⁰.

Effects on blood pressure and heart rate

This drug decreases heart rate and blood pressure in humans ^4,6. Despite this, rebound hypertension and tachycardia along with increased spasticity can occur when tizanidine is abruptly discontinued ⁸.

Mechanism of action

Tizanidine reduces spasticity by causing presynaptic inhibition of motor neurons via agonist actions at Alpha-2 adrenergic receptor sites. This drug is centrally acting and leads to a reduction in the release of excitatory amino acids like glutamate and aspartate, which cause neuronal firing that leads to muscle spasm. The above reduction and excitatory neurotransmitter release results in presynaptic inhibition of motor neurons. The strongest effect of tizanidine has been shown to occur on spinal polysynaptic pathways. The anti-nociceptive and anticonvulsant activities of tizanidine may also be attributed to agonist action on Alpha-2 receptors. Tizanidine also binds with weaker affinity to the Alpha-1 receptors, explaining its slight and temporary effect on the cardiovascular system ⁹.

Target	Actions	Organism
UAlpha-2 adrenergic receptors	agonist	Humans
NNischarin	agonist	Humans
UAlpha-1 adrenergic receptors	agonist	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

This drug undergoes significant first-pass metabolism. After the administration of an oral dose, tizanidine is mostly absorbed. The absolute oral bioavailability of tizanidine is measured to be about 40% ^Label.

Effect of food on absorption

Food has been shown to increase absorption for both the tablets and capsules. The increase in absorption with the tablet (about 30%) was noticeably higher than the capsule (~10%). When the capsule and tablet were administered with food, the amount absorbed from the capsule was about 80% of the amount absorbed from the tablet ^Label. It is therefore advisable to take this drug with food for increased absorption, especially in tablet form.

Volume of distribution

Extensively distributed throughout the body. The average steady-state volume of distribution is 2.4 L/kg ^Label.

Protein binding

About 30% bound to plasma proteins ^Label.

Metabolism

About 95% of the ingested dose of tizanidine is metabolized. The main enzyme involved in the hepatic metabolism of tizanidine is CYP1A2 ^Label.

• Tizanidine
  5-chloro-4-(guanidino)-2,1,3-benzothiadiazole
• Tizanidine
  5-chloro-4-(2- imidazolin-4-on-2-ylamino)-2,1,3-benzothiazdiazole

Route of elimination

This drug is mainly eliminated by the kidney ^Label.

Half life

Approximately 2.5 hours ^Label.

Clearance

A note on renal impairment

Tizanidine clearance is found to be decreased by more than 50% in elderly patients with renal insufficiency (creatinine clearance < 25 mL/min) compared to healthy elderly subjects; this would be expected to lead to a longer duration of clinical effect. This drug should be used with caution in patients with renal impairment ^Label.

Toxicity

LD50 information

Oral LD50 (rat): 414 mg/kg; Subcutaneous LD50 (rat): 282 mg/kg; Oral LD50 (mouse): 235 mg/kg ^MSDS

Use in pregnancy

Animal studies have determined that this drug causes fetal harm ^Label. Studies have not been performed in humans, and it is advisable to ensure that tizanidine use in pregnant women should be reserved for cases in which possible benefit clearly outweighs the possible risk to mother and unborn child ¹¹.

Use in breastfeeding

In studies of rat models, this tizanidine was found excreted in the breastmilk with a milk-to-blood ratio of 1.8:1 ^Label. In young nursing rats, abnormal results were obtained in tests indicative of central nervous system function. Various developmental changes that may have been attributable to the drug were observed. It is unknown whether tizanidine is excreted in human milk. It is a lipid-soluble drug, however, and likely to be excreted into breast milk ¹¹.

Carcinogenesis and mutagenesis

No signs of carcinogenicity were observed in two dietary studies performed in rodent models. Tizanidine was given to mice for 78 weeks at doses reaching a maximum 16 mg/kg (equivalent to twice the maximum recommended human dose). In addition, the drug was given to rats for 104 weeks at doses reaching 9 mg/kg (equivalent to 2.5 times the maximum recommended human dose). There was a lack of a statistically significant increase in the occurrence of tumors in either study group ¹¹.

Tizanidine was not found to be mutagenic or clastogenic in several laboratory essays, including the bacterial Ames test, the mammalian gene mutation test, in addition to the chromosomal aberration test in Chinese hamster cells and several other assays ¹¹.

Affected organisms

• Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Tizanidine.
1-benzylimidazole	The therapeutic efficacy of Tizanidine can be decreased when used in combination with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamine	The risk or severity of Tachycardia can be increased when Tizanidine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Tizanidine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthine	Tizanidine may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Tizanidine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Tizanidine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Tizanidine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanine	Tizanidine may increase the excretion rate of 6-O-benzylguanine which could result in a lower serum level and potentially a reduction in efficacy.
7-Deazaguanine	Tizanidine may increase the excretion rate of 7-Deazaguanine which could result in a lower serum level and potentially a reduction in efficacy.

Additional Data Available

Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
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Evidence Level
Evidence Level
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Action
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Food Interactions

• Avoid alcohol.
• Take with or without food. Maintain the same schedule with regard to meals, as concentrations increase in the fasted state and decrease in the fed state.

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.

US20110263863

General References

1. Henney HR 3rd, Runyan JD: A clinically relevant review of tizanidine hydrochloride dose relationships to pharmacokinetics, drug safety and effectiveness in healthy subjects and patients. Int J Clin Pract. 2008 Feb;62(2):314-24. doi: 10.1111/j.1742-1241.2007.01660.x. [PubMed:18199279]
2. Malanga G, Reiter RD, Garay E: Update on tizanidine for muscle spasticity and emerging indications. Expert Opin Pharmacother. 2008 Aug;9(12):2209-15. doi: 10.1517/14656566.9.12.2209 . [PubMed:18671474]
3. Wagstaff AJ, Bryson HM: Tizanidine. A review of its pharmacology, clinical efficacy and tolerability in the management of spasticity associated with cerebral and spinal disorders. Drugs. 1997 Mar;53(3):435-52. doi: 10.2165/00003495-199753030-00007. [PubMed:9074844]
4. Mathias CJ, Luckitt J, Desai P, Baker H, el Masri W, Frankel HL: Pharmacodynamics and pharmacokinetics of the oral antispastic agent tizanidine in patients with spinal cord injury. J Rehabil Res Dev. 1989 Fall;26(4):9-16. [PubMed:2600869]
5. Mense S: Muscle pain: mechanisms and clinical significance. Dtsch Arztebl Int. 2008 Mar;105(12):214-9. doi: 10.3238/artzebl.2008.0214. Epub 2008 Mar 21. [PubMed:19629211]
6. Taittonen M, Raty H, Kirvela O, Aantaa R, Kanto J: The metabolic effects of oral tizanidine in healthy volunteers. Acta Anaesthesiol Scand. 1995 Jul;39(5):628-32. [PubMed:7572012]
7. Chang E, Ghosh N, Yanni D, Lee S, Alexandru D, Mozaffar T: A Review of Spasticity Treatments: Pharmacological and Interventional Approaches. Crit Rev Phys Rehabil Med. 2013;25(1-2):11-22. doi: 10.1615/CritRevPhysRehabilMed.2013007945. [PubMed:25750484]
8. Suarez-Lledo A, Padulles A, Lozano T, Cobo-Sacristan S, Colls M, Jodar R: Management of Tizanidine Withdrawal Syndrome: A Case Report. Clin Med Insights Case Rep. 2018 Feb 13;11:1179547618758022. doi: 10.1177/1179547618758022. eCollection 2018. [PubMed:29467587]
9. Shirin Ghanavatian; Armen Derian (2019). Tizanidine. StatPearls.
10. Reflexes: Components of a Reflex Arc [Link]
11. Canadian monograph, Tizanidine [File]

External Links

Human Metabolome Database

HMDB0060964

KEGG Compound

C07452

PubChem Compound

5487

PubChem Substance

46505373

ChemSpider

5287

BindingDB

50240671

RxNav

57258

ChEBI

63629

ChEMBL

CHEMBL1079

ZINC

ZINC000019702309

Therapeutic Targets Database

DAP000234

PharmGKB

PA451701

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Tizanidine

ATC Codes

M03BX02 — Tizanidine

• M03BX — Other centrally acting agents
• M03B — MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
• M03 — MUSCLE RELAXANTS
• M — MUSCULO-SKELETAL SYSTEM

AHFS Codes

• 12:20.04 — Centrally Acting Skeletal Muscle Relaxants

FDA label

Download (329 KB)

MSDS

Download (24.2 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Basic Science	Substance, Addiction	1
1	Completed	Other	Malignant Melanoma, Neoplasms	1
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Traumatic Brain Injury (TBI)	1
1	Terminated	Treatment	Spasticity Due to Cerebral Palsy	1
1, 2	Completed	Treatment	Spasticity, Muscle	1
1, 2	Terminated	Treatment	Disseminated Sclerosis / Spasticity	1
2	Completed	Treatment	Spasticity	1
2	Withdrawn	Treatment	Acute Muscle Pain	1
3	Completed	Treatment	Back Pain Lower Back	1
3	Completed	Treatment	Disseminated Sclerosis / Spasticity, Muscle / Spinal Cord Injuries (SCI) / Stroke	1
3	Completed	Treatment	Vertebrogenic Radiculopathy L5, S1	1
4	Completed	Treatment	Back Pain Lower Back	1
4	Completed	Treatment	Thyroidectomy	1
4	Completed	Treatment	Unilateral Inguinal Hernia	1
4	Completed	Treatment	Upper Limb Spasticity	1
Not Available	Completed	Not Available	Arthritis / Gouty Arthritis / Headache / Migraine / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis	1

Pharmacoeconomics

Manufacturers

• Acorda therapeutics inc
• Actavis elizabeth llc
• Actavis totowa llc
• Alphapharm party ltd
• Apotex inc
• Barr laboratories inc
• Caraco pharmaceutical laboratories ltd
• Corepharma llc
• Dr reddys laboratories inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Mylan pharmaceuticals inc
• Sandoz inc
• Teva pharmaceuticals usa inc

Packagers

• Acorda Therapeutics
• Aidarex Pharmacuticals LLC
• Alphapharm Party Ltd.
• Altura Pharmaceuticals Inc.
• Amerisource Health Services Corp.
• Amneal Pharmaceuticals
• Apotex Inc.
• A-S Medication Solutions LLC
• Bryant Ranch Prepack
• Caraco Pharmaceutical Labs
• Cardinal Health
• Corepharma LLC
• Deca Pharmaceuticals LLC
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Doctor Reddys Laboratories Ltd.
• Elan Pharmaceuticals Inc.
• Eon Labs
• Genpharm LP
• H.J. Harkins Co. Inc.
• Heartland Repack Services LLC
• Innoviant Pharmacy Inc.
• Ivax Pharmaceuticals
• Keltman Pharmaceuticals Inc.
• Lake Erie Medical and Surgical Supply
• Major Pharmaceuticals
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Par Pharmaceuticals
• Patheon Inc.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Prepak Systems Inc.
• Rebel Distributors Corp.
• Redpharm Drug
• Resource Optimization and Innovation LLC
• Southwood Pharmaceuticals
• St Mary's Medical Park Pharmacy
• Stat Rx Usa
• Torpharm Inc.
• UDL Laboratories
• Vangard Labs Inc.

Dosage forms

Form	Route	Strength
Kit	Topical	4 mg/1
Tablet	Oral
Tablet	Oral	2 mg/1
Tablet	Oral	2 mg
Tablet	Oral	4 mg
Capsule	Oral	2 mg/1
Capsule, gelatin coated	Oral	2 mg/1
Capsule, gelatin coated	Oral	6 mg/1
Tablet	Oral	4 mg/1
Capsule	Oral	4 mg/1
Capsule	Oral	6 mg/1
Capsule, gelatin coated	Oral	4 mg/1

Prices

Unit description	Cost	Unit
Zanaflex 6 mg capsule	4.79USD	capsule
Zanaflex 4 mg capsule	3.2USD	capsule
Zanaflex 2 mg capsule	2.52USD	capsule
Zanaflex 4 mg tablet	2.29USD	tablet
Tizanidine hcl 4 mg tablet	1.49USD	tablet
Zanaflex 2 mg tablet	1.42USD	tablet
Tizanidine hcl 2 mg tablet	1.25USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
US6455557	No	2002-09-24	2021-11-28

Additional Data Available

Filed On
Filed On
The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	280	https://www.lookchem.com/Tizanidine-hydrochloride/
boiling point (°C)	391.2	https://www.lookchem.com/Tizanidine/
water solubility	slightly soluble	FDA label
logP	1.72	https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL1079/
pKa	7.48	https://www.ebi.ac.uk/chembl/compound_report_card/CHEMBL1079/

Predicted Properties

Property	Value	Source
Water Solubility	0.133 mg/mL	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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.8592
Caco-2 permeable	+	0.5323
P-glycoprotein substrate	Substrate	0.6545
P-glycoprotein inhibitor I	Non-inhibitor	0.8365
P-glycoprotein inhibitor II	Non-inhibitor	0.7953
Renal organic cation transporter	Inhibitor	0.6577
CYP450 2C9 substrate	Non-substrate	0.7953
CYP450 2D6 substrate	Non-substrate	0.8018
CYP450 3A4 substrate	Non-substrate	0.5795
CYP450 1A2 substrate	Non-inhibitor	0.5248
CYP450 2C9 inhibitor	Non-inhibitor	0.7117
CYP450 2D6 inhibitor	Non-inhibitor	0.7867
CYP450 2C19 inhibitor	Non-inhibitor	0.6353
CYP450 3A4 inhibitor	Non-inhibitor	0.781
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.5
Ames test	Non AMES toxic	0.6538
Carcinogenicity	Non-carcinogens	0.8915
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.6573 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.6935
hERG inhibition (predictor II)	Non-inhibitor	0.8907

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-0udi-5490000000-5ee0610f321160b63c82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description

This compound 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

Benzenoids / Aryl chlorides / Thiadiazoles / Imidazolines / Heteroaromatic compounds / Guanidines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Azacyclic compounds / Organopnictogen compoundsOrganochlorides / Hydrocarbon derivatives

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Substituents

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

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Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazoles, benzothiadiazole (CHEBI:63629)

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Drug created on June 13, 2005 07:24 / Updated on June 02, 2020 00:54