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Muscle relaxant medication
Tizanidine Pronunciation tye-ZAN -i-deen Trade names Zanaflex, Sirdalud, and others Other names 4-Chloro-N H AHFS /Drugs.com Monograph MedlinePlus a601121 License data
Routes of By mouth Drug class α2 ATC code Legal status
UK POM (Prescription only)
US ℞-only
Bioavailability ~40%[1] Protein binding ~30% Metabolism Liver (CYP1A2 , 95%)Elimination half-life 2.54 hours (tizanidine), 20–40 hours (inactive metabolites)[1] Excretion Urine (60%), feces (20%)
5-Chloro-N H c ] [1,2,5]thiadiazol-4-amine
CAS Number PubChem CID DrugBank ChemSpider UNII KEGG
as HCl: D00776 Y
ChEMBL CompTox Dashboard (EPA ) ECHA InfoCard 100.125.400 Formula C 9 H 8 Cl N 5 S Molar mass −1 3D model (JSmol )
Clc1ccc3nsnc3c1NC/2=N/CCN\2
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) Y
Key:XFYDIVBRZNQMJC-UHFFFAOYSA-N Y
(verify)
Tizanidine , sold under the brand name Zanaflex among others, is an alpha-2 (α2 agonist,[2] clonidine , that is used to treat muscle spasticity due to spinal cord injury , multiple sclerosis , and spastic cerebral palsy .[3] baclofen or diazepam .[4] by mouth .[5]
Common side effects of tizanidine include dry mouth , sleepiness , weakness , and dizziness .[5] low blood pressure , liver problems , psychosis , and QT prolongation .[5] pregnancy and breastfeeding is safe.[6] α2 , but how it works is not entirely clear.[5]
Tizanidine was approved for medical use in the United States in 1996.[5] generic medication .[3] million prescriptions.[7] [8]
Medical uses [ edit ]
Tizanidine has been found to be as effective as other antispasmodic drugs and is more tolerable than baclofen and diazepam .[4]
Side effects [ edit ]
Side effects include dizziness, drowsiness, weakness, nervousness, confusion, hallucinations , strange dreams, depression, vomiting, dry mouth, constipation, diarrhea, stomach pain, heartburn, increased muscle spasms, back pain, rash, sweating, and a tingling sensation in the arms, legs, hands, and feet.[9]
Symptoms of overdose in 45 cases reported to a poison control center included: lethargy, bradycardia, hypotension, agitation, confusion, vomiting and coma.[10]
Interactions [ edit ]
Concomitant use of tizanidine and moderate or potent CYP1A2 inhibitors (such as zileuton , certain antiarrhythmics (amiodarone , mexiletine , propafenone , verapamil ), cimetidine , famotidine , aciclovir , ticlopidine and oral contraceptives ) is contraindicated. Concomitant use of tizanidine with fluvoxamine , a potent CYP1A2 inhibitor in humans, resulted in a 33-fold increase in the tizanidine AUC (plasma drug concentration-time curve).[1] fluvoxamine and tizanidine should not be taken at the same time. Fluoroquinolone antibiotics such as moxifloxacin , levofloxacin , and ciprofloxacin should also be avoided due to an increased serum concentration of tizanidine when administered concomitantly.[11] central nervous system depressants . Alcohol should be avoided, particularly as it can upset the stomach. The CNS-depressant effects of tizanidine and alcohol are additive.[1] interactions :[12] [13] [14]
antibiotics such as enoxacin , gatifloxacin , levofloxacin , lomefloxacin , moxifloxacin , ofloxacin , sparfloxacin , trovafloxacin , or norfloxacin ;
blood pressure medications such as clonidine , guanabenz , guanfacine (Tenex), or methyldopa ;
heart rhythm medications such as amiodarone (Cordarone, Pacerone), mexiletine (Mexitil), propafenone (Rhythmol), and verapamil (Calan, Covera, Isoptin).
Pharmacology [ edit ]
Tizanidine is an α2 agonist closely related to clonidine . It has approximately one tenth to one fifteenth of the blood pressure lowering effect of clonidine. The relation between the α2 [2]
Route of administration [ edit ]
Tizanidine is available as a tablet or capsule. Capsules may be opened and sprinkled on food. However, this may change the absorption of the medication compared to taking the capsule whole.[16] volume of distribution of 2.4 L/kg following intravenous administration.[1]
Chemistry [ edit ]
Tizanidine is a derivative of 2,1,3-benzothiadiazole and its first published synthesis was reported in a patent.[17] [18] thionyl chloride in pyridine formed the heterocycle , which was nitrated with sodium nitrate in sulfuric acid and reduced using iron and acetic acid.
The amine intermediate was treated with benzoyl chloride and ammonium thiocyanate followed by alkaline hydrolysis to form a thiourea . This was activated as its isothiuronium salt before being treated with ethylene diamine to give tizanidine.[17] [19]
References [ edit ]
^ a b British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1094. ISBN 9780857113382
^ a b Kamen L, Henney HR, Runyan JD (February 2008). "A practical overview of tizanidine use for spasticity secondary to multiple sclerosis, stroke, and spinal cord injury". Current Medical Research and Opinion . 24 2 ): 425–439. doi :10.1185/030079908X261113 . PMID 18167175 . S2CID 73086671 .
^ a b c d e "Tizanidine Hydrochloride Monograph for Professionals" . Drugs.com . American Society of Health-System Pharmacists. Retrieved 3 March 2019 .
^ "Tizanidine Pregnancy and Breastfeeding Warnings" . Drugs.com . Retrieved 3 March 2019 .
^ "The Top 300 of 2021" . ClinCalc . Archived from the original on 15 January 2024. Retrieved 14 January 2024 .
^ "Tizanidine - Drug Usage Statistics" . ClinCalc . Retrieved 14 January 2024 .
^ "Page not available" . PubMed Health . Archived from the original on 11 November 2012. Retrieved 4 September 2017 .
^ Spiller HA, Bosse GM, Adamson LA (January 2004). "Retrospective review of Tizanidine (Zanaflex) overdose". Journal of Toxicology. Clinical Toxicology . 42 5 ): 593–596. doi :10.1081/CLT-200026978 . PMID 15462150 . S2CID 38946270 .
^ "Tizanidine Uses, Dosage, Side Effects – Drugs.com" . drugs.com . Retrieved 4 September 2017 .
^ NHS Wales (2011). "Tizanidine (Zanaflex) Gwent Primary Care Prescribing Guidance" (PDF) . Aneurin Bevan University Health Board.
^ "Tizanidine package leaflet: Information for the user" (PDF) . Medicines and Healthcare products Regulatory Agency (UK ). 2016. Archived from the original (PDF) on 16 September 2018. Retrieved 16 September 2018 .
^ "Zanaflex (tizanidine hydrochloride) dose, indications, adverse effects, interactions... from PDR.net" . www.pdr.net . Retrieved 16 September 2018 .
^ a b c Blaxall HS, Murphy TJ, Baker JC, Ray C, Bylund DB (October 1991). "Characterization of the alpha-2C adrenergic receptor subtype in the opossum kidney and in the OK cell line". The Journal of Pharmacology and Experimental Therapeutics . 259 (1 ): 323–329. PMID 1656026 .
^ "Tizanidine: MedlinePlus Drug Information" . medlineplus.gov . U.S. National Library of Medicine. Retrieved 29 October 2019 .
^ a b US patent 3843668 , Neumann P, "Certain 4-substituted amino-2,1,3-benzothiadiozoles", published 1974-10-22, assigned to Sandoz AG
^ Pesin VG, Sergeev VA (1969). "Research on 2,1,3-thia- and selenadiazole". Chemistry of Heterocyclic Compounds . 3 5 ): 662–666. doi :10.1007/BF00468340 . S2CID 98830770 .
^ "Pharmaceutical Substances: Tizanidine" . Thieme. Retrieved 16 February 2023 .
t
e
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Alfuzosin
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Atiprosin
Atypical antipsychotics (e.g., brexpiprazole , clozapine , olanzapine , quetiapine , risperidone )
Benoxathian
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Buflomedil
Bunazosin
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Dapiprazole
Domesticine
Doxazosin
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Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
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Phenylpiperazine antidepressants (e.g., hydroxynefazodone , nefazodone , trazodone , triazoledione )
Piperoxan
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Tamsulosin
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Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , imipramine , trimipramine )
Trimazosin
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )
Urapidil
WB-4101
Zolertine
α2
Agonists
Antagonists
1-PP
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g., asenapine , brexpiprazole , clozapine , lurasidone , olanzapine , paliperidone , quetiapine , risperidone , zotepine )
Azapirones (e.g., buspirone , gepirone , ipsapirone , tandospirone )
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g., chlorpromazine , fluphenazine , loxapine , thioridazine )
Yohimbine
β
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Tizanidine&oldid=1231497400 " C a t e g o r i e s : ● M u s c l e r e l a x a n t s ● A l p h a - 2 a d r e n e r g i c r e c e p t o r a g o n i s t s ● I m i d a z o l i n e s ● D r u g s d e v e l o p e d b y N o v a r t i s ● O r g a n o c h l o r i d e s ● B e n z o t h i a d i a z o l e s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a ● U s e A m e r i c a n E n g l i s h f r o m S e p t e m b e r 2 0 1 7 ● A l l W i k i p e d i a a r t i c l e s w r i t t e n i n A m e r i c a n E n g l i s h ● U s e d m y d a t e s f r o m F e b r u a r y 2 0 2 4 ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● M u l t i p l e c h e m i c a l s i n I n f o b o x d r u g ● C h e m i c a l s u s i n g i n d e x l a b e l s ● D r u g b o x e s w h i c h c o n t a i n c h a n g e s t o w a t c h e d f i e l d s ● W i k i p e d i a m e d i c i n e a r t i c l e s r e a d y t o t r a n s l a t e
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a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
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