Structure via PubChem · Public domain (PubChem)
tizanidine
Sign in to saveAlso known as AN-021, DS-103-282, Zanaflex®, Tizanidina, Tizanidin, Tizanidinum, 5-Chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole
Tizanidine, sold under the brand name Zanaflex among others, is an alpha-2 (α2) adrenergic receptor agonist, similar to clonidine, that is used to treat muscle spasticity due to spinal cord injury, multiple sclerosis, and spastic cerebral palsy. Effectiveness appears similar to baclofen or diazepam. It is taken by mouth.
Key facts
- Drug.bioavailability
- ~40%
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470611127
- Drug.image
- Tizanidine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 190
- Drug.image2
- Tizanidine-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Zanaflex, Sirdalud, and others
- Drug.MedlinePlus
- a601121
- Drug.DailyMedID
- Tizanidine
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- M03
- Drug.ATC_suffix
- BX02
- Drug.class
- α2-adrenergic receptor agonist
- Drug.legal_US
- Rx-only
- Drug.protein_bound
- ~30%
- Drug.metabolism
- Liver (CYP1A2, 95%)
via Wikipedia infobox
Chemical data
- Formula
- C9H8ClN5S
- Molecular weight
- 253.71 g/mol
- IUPAC name
- 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine
- SMILES
- C1CN=C(N1)NC2=C(C=CC3=NSN=C32)Cl
- InChIKey
- XFYDIVBRZNQMJC-UHFFFAOYSA-N
- XLogP
- 1.1
- Polar surface area
- 90.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1996
- Admin. routes
- oral
- Indications
- melanoma, pain, Spasticity
via ChEMBL · EBI
Research
713 papers- Tizanidine.2006
- Tizanidine.2012
- Tizanidine: Advances in Pharmacology & Therapeutics and Drug Formulations.Journal of pain research · 2024
- Tizanidine.2026
- Tizanidine Induced Hypotension: Report of a Case and Review of the Literature.Current drug safety · 2024
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- carbon
- Mass
- 253.019
- Has use
- medication
Show 9 more facts
- significant drug interaction
- ticlopidine
- chemical formula
- C₉H₈ClN₅S
- defined daily dose
- 12
- medical condition treated
- muscle cramp
- canonical SMILES
- C1CN=C(N1)NC2=C(C=CC3=NSN=C32)Cl
- World Health Organisation international non-proprietary name
- tizanidine
- subject has role
- parasympatholytic
- stylized name
- tiZANidine
- Commons category
- Tizanidine
via Wikidata · CC0
~5 min read
Encyclopedic overview
7 sectionsContents
- Medical uses
- Side effects
- Interactions
- Pharmacology
- Route of administration
- Chemistry
- References
Tizanidine, sold under the brand name Zanaflex among others, is an alpha-2 (α2) adrenergic receptor agonist, similar to clonidine, that is used to treat muscle spasticity due to spinal cord injury, multiple sclerosis, and spastic cerebral palsy. Effectiveness appears similar to baclofen or diazepam. It is taken by mouth.
Common side effects of tizanidine include dry mouth, sleepiness, weakness, and dizziness. Serious side effects may include low blood pressure, liver problems, psychosis, and QT prolongation. It is unclear if use in pregnancy and breastfeeding is safe. It is an α2-adrenergic agonist, but how it works is not entirely clear.
Excerpted from Wikipedia’s “tizanidine” article, available under the CC BY-SA 4.0 licence.