Tizanidine

Identification

Summary

Tizanidine is an alpha-2 adrenergic agonist used for the short-term treatment of muscle spasticity.

Brand Names

Zanaflex

Generic Name

Tizanidine

DrugBank Accession Number

DB00697

Background

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.

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 253.711
Monoisotopic: 253.018893678
Chemical Formula: C₉H₈ClN₅S

Synonyms

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

External IDs

AN 021
DS 103-282

Poor quality drug data slowing you down?

Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.

Download eBook

Poor quality drug data slowing you down?

Download eBook

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.

Reduce drug development failure rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Associated Conditions

Indication Type	Indication	Approval Level
Treatment of	Acute low back pain	••• •••••
Treatment of	Drug withdrawal headache	••• •••••
Treatment of	Insomnia	••• •••••
Treatment of	Migraine	••• •••••
Management of	Muscle spasticity	••••••••••••

Associated Therapies

Withdrawal From Addictive Substance; Detoxification

Contraindications & Blackbox Warnings

Prevent Adverse Drug Events Today

Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events with our Clinical API

Learn more

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
NNischarin	agonist	Humans
UAlpha-1 adrenergic receptors	agonist	Humans
UAlpha-2 adrenergic receptors	agonist	Humans

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.

Hover over products below to view reaction partners

Tizanidine
- 5-chloro-4-(guanidino)-2,1,3-benzothiadiazole
- 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.

Adverse Effects

Improve decision support & research outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!

See the data

Improve decision support & research outcomes with our structured adverse effects data.

See a data sample

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.

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
Integrate drug-drug interactions in your software
1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Tizanidine is combined with 1,2-Benzodiazepine.
Abaloparatide	The risk or severity of adverse effects can be increased when Tizanidine is combined with Abaloparatide.
Abametapir	The serum concentration of Tizanidine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Tizanidine can be increased when combined with Abatacept.
Abiraterone	The serum concentration of Tizanidine can be increased when it is combined with Abiraterone.

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.

Products

Drug product information from 10+ global regions

Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.

Access now

Access drug product information from over 10 global regions.

Access now

Product Ingredients

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

Product Images

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)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Tizanidine Hydrochloride	Capsule, gelatin coated	6 mg/1	Oral	bryant ranch prepack	2012-02-06	Not applicable
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	2 mg/1	Oral	Clinical Solutions Wholsesale	2012-02-06	2017-06-21
Zanaflex	Tablet	4 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	1997-01-01	2020-09-30
Zanaflex	Capsule	6 mg/1	Oral	Acorda Therapeutics, Inc.	2005-04-04	2019-03-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-tizanidine	Tablet	4 mg	Oral	Apotex Corporation	2004-11-17	Not applicable
Apo-tizanidine	Tablet	2 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Comfort Pac with Tizanidine	Kit; Tablet	4 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2013-07-09	2018-12-17
Mint-tizanidine	Tablet	4 mg	Oral	Mint Pharmaceuticals Inc	2023-09-07	Not applicable
Mylan-tizanidine	Tablet	4 mg	Oral	Mylan Pharmaceuticals	2006-02-16	2017-01-09

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ALGI - B® TABLETAS	Tizanidine hydrochloride (2 mg) + Acetaminophen (325 mg)	Tablet, coated	Oral		2010-05-27	Not applicable
FLECTADOL CAPSULAS	Tizanidine hydrochloride (2 mg) + Ibuprofen (400 mg)	Capsule, coated	Oral	C.I. FARMACAPSULAS S.A.S. - PLANTA NO. 2	2006-11-10	2015-09-03
MIALGILOX	Tizanidine (2 mg) + Ibuprofen (400 mg)	Capsule, coated	Oral	SEVERIANO FERNÁNDEZS.A.S	2017-12-01	Not applicable
MYOS -NOR F TABLETAS	Tizanidine hydrochloride (2 mg) + Ibuprofen (200 mg)	Tablet, coated	Oral	BLISTECO S.A.S.	2008-11-07	Not applicable
TIZAFEN® TABLETA RECUBIERTA	Tizanidine hydrochloride (2 mg) + Acetaminophen (350 mg)	Tablet, coated	Oral	LABORATORIOSSIEGFRIED S.A.S	2006-11-10	Not applicable

Chemical Identifiers

UNII: 6AI06C00GW
CAS number: 51322-75-9
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

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

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. [Article]
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 . [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
Shirin Ghanavatian; Armen Derian (2019). Tizanidine. StatPearls.
Reflexes: Components of a Reflex Arc [Link]
Canadian monograph, Tizanidine [File]

External Links

Human Metabolome Database: HMDB0014835
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

FDA label

Download (329 KB)

MSDS

Download (24.2 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
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
4	Recruiting	Treatment	Shoulder Arthropathy / Shoulder Pain	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
Tablet, coated	Oral
Capsule, extended release	Oral	6 mg
Kit; tablet	Oral	4 mg/1
Capsule	Oral	15.000 mg
Solution / drops
Tablet	Oral	400000 mg
Capsule, coated	Oral
Tablet	Oral	0.002 g
Tablet, film coated	Oral	4 mg
Tablet, film coated	Oral	400000 mg
Solution / drops; tablet	Ophthalmic
Capsule, delayed release		6 mg
Tablet	Oral	2.288 mg
Tablet	Oral
Tablet	Oral	6 MG
Capsule	Oral	6 mg
Tablet	Oral	200000 mg
Tablet	Oral	2 mg/1
Capsule	Oral	2 mg/1
Capsule, gelatin coated	Oral	2 mg/1
Capsule, gelatin coated	Oral	6 mg/1
Tablet	Oral	4 mg/1
Tablet, film coated	Oral
Capsule	Oral	4 mg/1
Capsule	Oral	6 mg/1
Capsule, gelatin coated	Oral	4 mg/1
Tablet	Oral	2 mg
Tablet	Oral	4 mg

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)	Region
US6455557	No	2002-09-24	2021-11-28

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	splash10-0a4i-3960000000-3aca4c577af73cfa3997
Mass Spectrum (Electron Ionization)	MS	splash10-0udi-5490000000-5ee0610f321160b63c82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0090000000-425432ba738571ef78a8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-1090000000-6095a8134c8c22b9ea88
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-0090000000-1771655e532ce4034040
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9500000000-6aa2874f4d8f69b1cc00
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-2950000000-98a6513db9d8a7e73d3c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-9100000000-fde5057917848f058e94
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	147.6872461	predicted	DarkChem Lite v0.1.0
[M-H]-	147.9733461	predicted	DarkChem Lite v0.1.0
[M-H]-	144.97597	predicted	DeepCCS 1.0 (2019)
[M+H]+	148.6281461	predicted	DarkChem Lite v0.1.0
[M+H]+	148.5304461	predicted	DarkChem Lite v0.1.0
[M+H]+	147.37154	predicted	DeepCCS 1.0 (2019)
[M+Na]+	148.0153461	predicted	DarkChem Lite v0.1.0
[M+Na]+	147.7531461	predicted	DarkChem Lite v0.1.0
[M+Na]+	153.41367	predicted	DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	28	N/A	N/A	A28809

Details1. Nischarin

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Agonist

General Function: Phosphatidylinositol binding
Specific Function: Acts either as the functional imidazoline-1 receptor (I1R) candidate or as a membrane-associated mediator of the I1R signaling. Binds numerous imidazoline ligands that induces initiation of cell-si...
Gene Name: NISCH
Uniprot ID: Q9Y2I1
Uniprot Name: Nischarin
Molecular Weight: 166627.105 Da

References

Tanabe M, Hashimoto M, Ono H: Imidazoline I(1) receptor-mediated reduction of muscle rigidity in the reserpine-treated murine model of Parkinson's disease. Eur J Pharmacol. 2008 Jul 28;589(1-3):102-5. doi: 10.1016/j.ejphar.2008.06.013. Epub 2008 Jun 7. [Article]
Talakoub R, Abbasi S, Maghami E, Zavareh SM: The effect of oral tizanidine on postoperative pain relief after elective laparoscopic cholecystectomy. Adv Biomed Res. 2016 Feb 8;5:19. doi: 10.4103/2277-9175.175905. eCollection 2016. [Article]
Canadian monograph, Tizanidine [File]
FDA label, Zanaflex [File]

Details2. Alpha-1 adrenergic receptors (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:

Name	UniProt ID
Alpha-1A adrenergic receptor	P35348
Alpha-1B adrenergic receptor	P35368
Alpha-1D adrenergic receptor	P25100

References

Takayanagi I, Konno F, Ishii C, Takemasa T, Yanagida Y, Shimizu M, Mori H, Sugane H: Actions of tizanidine on alpha 1-and alpha 2-adrenoceptors in the peripheral tissues. Gen Pharmacol. 1984;15(3):239-41. [Article]
Takayanagi I, Harada M, Koike K, Satoh M: Differences in alpha 1-adrenoceptor mechanisms for phenylephrine and tizanidine in rabbit thoracic aorta and common iliac artery. Can J Physiol Pharmacol. 1991 Dec;69(12):1819-24. [Article]
Shirin Ghanavatian; Armen Derian (2019). Tizanidine. StatPearls.

Details3. Alpha-2 adrenergic receptors (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Thioesterase binding
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 oxymetazo...

Components:

Name	UniProt ID
Alpha-2A adrenergic receptor	P08913
Alpha-2B adrenergic receptor	P18089
Alpha-2C adrenergic receptor	P18825

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. [Article]
Giovannitti JA Jr, Thoms SM, Crawford JJ: Alpha-2 adrenergic receptor agonists: a review of current clinical applications. Anesth Prog. 2015 Spring;62(1):31-9. doi: 10.2344/0003-3006-62.1.31. [Article]
Leiphart JW, Dills CV, Levy RM: Alpha2-adrenergic receptor subtype specificity of intrathecally administered tizanidine used for analgesia for neuropathic pain. J Neurosurg. 2004 Oct;101(4):641-7. doi: 10.3171/jns.2004.101.4.0641. [Article]
Fairbanks CA, Stone LS, Wilcox GL: Pharmacological profiles of alpha 2 adrenergic receptor agonists identified using genetically altered mice and isobolographic analysis. Pharmacol Ther. 2009 Aug;123(2):224-38. doi: 10.1016/j.pharmthera.2009.04.001. Epub 2009 Apr 23. [Article]
Zanaflex FDA label [File]

Enzymes

Details1. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

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. [Article]
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. [Article]
Karjalainen MJ, Neuvonen PJ, Backman JT: Rofecoxib is a potent, metabolism-dependent inhibitor of CYP1A2: implications for in vitro prediction of drug interactions. Drug Metab Dispos. 2006 Dec;34(12):2091-6. doi: 10.1124/dmd.106.011965. Epub 2006 Sep 19. [Article]
Flockhart Table of Drug Interactions [Link]
Tizanidine FDA label [File]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Tizanidine

Identification

Structure for Tizanidine (DB00697)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

Components:

References

Components:

References

Enzymes

References