Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H8ClN5S |
Molecular Weight | 253.711 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=C(NC2=NCCN2)C3=NSN=C3C=C1
InChI
InChIKey=XFYDIVBRZNQMJC-UHFFFAOYSA-N
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)
Molecular Formula | C9H8ClN5S |
Molecular Weight | 253.711 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00697 | https://www.drugs.com/tizanidine.html | http://reference.medscape.com/drug/zanaflex-tizanidine-343071
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB00697 | https://www.drugs.com/tizanidine.html | http://reference.medscape.com/drug/zanaflex-tizanidine-343071
Tizanidine is a short-acting drug for the management of spasticity. Tizanidine is an agonist at a2-adrenergic receptor sites and presumably reduces spasticity by increasing presynaptic inhibition of motor neurons. In animal models, tizanidine has no direct effect on skeletal muscle fibers or the neuromuscular junction, and no major effect on monosynaptic spinal reflexes. The effects of tizanidine are greatest on polysynaptic pathways. The overall effect of these actions is thought to reduce facilitation of spinal motor neurons. Side effects include dizziness, drowsiness, weakness, nervousness, hallucinations, 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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095158 |
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Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15481719 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ZANAFLEX Approved UseTizanidine is a central alpha-2-adrenergic agonist indicated for the management of spasticity. Because of the short duration of therapeutic effect, treatment with tizanidine should be reserved for those daily activities and times when relief of spasticity is most important [see Dosage and Administration (2.1) Launch Date1996 |
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Primary | ZANAFLEX Approved UseTizanidine is a central alpha-2-adrenergic agonist indicated for the management of spasticity. Because of the short duration of therapeutic effect, treatment with tizanidine should be reserved for those daily activities and times when relief of spasticity is most important [see Dosage and Administration (2.1) Launch Date1996 |
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Primary | ZANAFLEX Approved UseTizanidine is a central alpha-2-adrenergic agonist indicated for the management of spasticity. Because of the short duration of therapeutic effect, treatment with tizanidine should be reserved for those daily activities and times when relief of spasticity is most important [see Dosage and Administration (2.1) Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.1 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3447935 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZANIDINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
11 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3447935 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZANIDINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3447935 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZANIDINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
54 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3447935 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZANIDINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3447935 |
5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZANIDINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3447935 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TIZANIDINE blood | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Disc. AE: Drowsiness, Fatigue... AEs leading to discontinuation/dose reduction: Drowsiness (5.9%) Sources: Page: p.716Fatigue (3.9%) Muscular weakness (3.9%) Affective disorder (3.9%) Bradycardia (2%) Ventricular extrasystoles (2%) Anxiety (2%) Sleep disturbance (2%) Syncope (2%) |
12 mg 3 times / day multiple, oral Recommended Dose: 12 mg, 3 times / day Route: oral Route: multiple Dose: 12 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Spasticity Sources: Page: p.1 |
Disc. AE: Hypotension, Liver injury... AEs leading to discontinuation/dose reduction: Hypotension Sources: Page: p.1Liver injury Sedation Hallucinations Renal impairment |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Anxiety | 2% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Bradycardia | 2% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Sleep disturbance | 2% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Syncope | 2% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Ventricular extrasystoles | 2% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Affective disorder | 3.9% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Fatigue | 3.9% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Muscular weakness | 3.9% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Drowsiness | 5.9% Disc. AE |
19.36 mg 3 times / day multiple, oral (mean) Recommended Dose: 19.36 mg, 3 times / day Route: oral Route: multiple Dose: 19.36 mg, 3 times / day Sources: Page: p.716 |
unhealthy, 18 - 77 n = 51 Health Status: unhealthy Condition: Spasticity Age Group: 18 - 77 Sex: M+F Population Size: 51 Sources: Page: p.716 |
Hallucinations | Disc. AE | 12 mg 3 times / day multiple, oral Recommended Dose: 12 mg, 3 times / day Route: oral Route: multiple Dose: 12 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Spasticity Sources: Page: p.1 |
Hypotension | Disc. AE | 12 mg 3 times / day multiple, oral Recommended Dose: 12 mg, 3 times / day Route: oral Route: multiple Dose: 12 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Spasticity Sources: Page: p.1 |
Liver injury | Disc. AE | 12 mg 3 times / day multiple, oral Recommended Dose: 12 mg, 3 times / day Route: oral Route: multiple Dose: 12 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Spasticity Sources: Page: p.1 |
Renal impairment | Disc. AE | 12 mg 3 times / day multiple, oral Recommended Dose: 12 mg, 3 times / day Route: oral Route: multiple Dose: 12 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Spasticity Sources: Page: p.1 |
Sedation | Disc. AE | 12 mg 3 times / day multiple, oral Recommended Dose: 12 mg, 3 times / day Route: oral Route: multiple Dose: 12 mg, 3 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Spasticity Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
---|---|---|
Pain and spasticity after spinal cord injury: mechanisms and treatment. | 2001 Dec 15 |
|
Management of spasticity, pain, and paroxysmal phenomena in multiple sclerosis. | 2001 May |
|
Evaluation of electromagnetic fields in the treatment of pain in patients with lumbar radiculopathy or the whiplash syndrome. | 2002 |
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[Clinical treatment (non surgical) of spasticity in cerebral palsy]. | 2002 Jan 1-15 |
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Determination of tizanidine in human plasma by gas chromatography-mass spectrometry. | 2002 Jul |
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Treatment of spasticity. | 2002 Jun |
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Low-dose tizanidine with nonsteroidal anti-inflammatory drugs for detoxification from analgesic rebound headache. | 2002 Mar |
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The medical management of spasticity. | 2002 May |
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Protective effects of dextromethorphan and tizanidine on ouabain-induced arrhythmias. | 2002 Sep |
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[Spastic syndrome and main directions of its treatment]. | 2003 |
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Treatments for spasticity and pain in multiple sclerosis: a systematic review. | 2003 |
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Preventative treatment for migraine and tension-type headaches : do drugs having effects on muscle spasm and tone have a role? | 2003 |
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[Intrathecal baclofen in the treatment of severe spastic tetraplegia and dystonia in children and adolescents]. | 2003 Apr 21 |
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Modulatory effects of alpha1-,alpha2-, and beta -receptor agonists on feline spinal interneurons with monosynaptic input from group I muscle afferents. | 2003 Jan 1 |
|
[Orally administered drugs in the treatment of spasticity]. | 2003 Jul 1-15 |
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Antihyperalgesic and side effects of intrathecal clonidine and tizanidine in a rat model of neuropathic pain. | 2003 Jun |
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Effects of intrathecally administered dexmedetomidine, MPV-2426 and tizanidine on EMG in rats. | 2003 Mar |
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Tizanidine is not a cure for chronic daily headache. | 2003 Mar |
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Continuous intrathecal clonidine and tizanidine in conscious dogs: analgesic and hemodynamic effects. | 2003 Mar |
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[Medical treatment of spasticity]. | 2003 May |
|
Stability-indicating HPTLC determination of tizanidine hydrochloride in bulk drug and pharmaceutical formulations. | 2003 Nov 24 |
|
High-dose tizanidine abuse. | 2003 Summer |
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Retrospective review of Tizanidine (Zanaflex) overdose. | 2004 |
|
A benefit-risk assessment of baclofen in severe spinal spasticity. | 2004 |
|
Effect of oral tizanidine on local-anesthetic infiltration pain during epidural catheterization. | 2004 Apr |
|
Fluvoxamine drastically increases concentrations and effects of tizanidine: a potentially hazardous interaction. | 2004 Apr |
|
Paraneoplastic "stiff person syndrome" with metastatic adenocarcinoma and anti-Ri antibodies. | 2004 Apr 27 |
|
Comparative efficacy and safety of skeletal muscle relaxants for spasticity and musculoskeletal conditions: a systematic review. | 2004 Aug |
|
Ciprofloxacin greatly increases concentrations and hypotensive effect of tizanidine by inhibiting its cytochrome P450 1A2-mediated presystemic metabolism. | 2004 Dec |
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Modulation of the transmission in group II heteronymous pathways by tizanidine in spastic hemiplegic patients. | 2004 Jan |
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Tizanidine for the treatment of intention myoclonus: a case series. | 2004 Jul |
|
Validated semiquantitative/quantitative screening of 51 drugs in whole blood as silylated derivatives by gas chromatography-selected ion monitoring mass spectrometry and gas chromatography electron capture detection. | 2004 Jul 5 |
|
Muscle relaxants in the treatment of myofascial face pain. A literature review. | 2004 Jun |
|
Tizanidine is mainly metabolized by cytochrome p450 1A2 in vitro. | 2004 Mar |
|
[Effects of tizanidine for refractory sleep disturbance in disabled children with spastic quadriplegia]. | 2004 Nov |
|
Hypotension due to interaction between lisinopril and tizanidine. | 2004 Nov |
|
Preventive migraine therapy: what is new. | 2004 Oct |
|
Alpha2-adrenergic receptor subtype specificity of intrathecally administered tizanidine used for analgesia for neuropathic pain. | 2004 Oct |
|
[Pharmacology and upper limb poststroke spasticity: a review. International Society of Prosthetics and Orthotics]. | 2004 Oct |
|
Oral antispastic drugs in nonprogressive neurologic diseases: a systematic review. | 2004 Oct 26 |
|
Simultaneous LC determination of tizanidine and rofecoxib in tablets. | 2005 Feb 7 |
|
Application of HPLC and HPTLC for the simultaneous determination of tizanidine and rofecoxib in pharmaceutical dosage form. | 2005 Feb 7 |
|
Assessment of efficacy and psychomotor performances of thiocolchicoside and tizanidine in patients with acute low back pain. | 2005 Jul |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
[Spasticity. Physical therapy, preventive measures and treatment]. | 2005 Jun |
|
Group II excitations from plantar foot muscles to human leg and thigh motoneurones. | 2005 Mar |
|
Rofecoxib is a potent, metabolism-dependent inhibitor of CYP1A2: implications for in vitro prediction of drug interactions. | 2006 Dec |
|
Botulinum toxin type A for the treatment of the spastic equinus foot in cerebral palsy. | 2006 Feb |
|
[The study and treatment of dystonias in childhood]. | 2006 Oct 10 |
|
Rofecoxib is a potent inhibitor of cytochrome P450 1A2: studies with tizanidine and caffeine in healthy subjects. | 2006 Sep |
Patents
Sample Use Guides
Recommended starting dose: 2 mg; dose can be repeated at 6 to 8 hour
intervals, up to a maximum of 3 doses in 24 hours
Dosage can be increased by 2 mg to 4 mg per dose, with 1 to 4 days
between increases; total daily dose should not exceed 36 mg
Tizanidine pharmacokinetics differs between tablets and capsules, and
when taken with or without food. These differences could result in a
change in tolerability and control of symptoms
To discontinue Zanaflex, decrease dose slowly to minimize the risk of
withdrawal and rebound hypertension, tachycardia, and hypertonia
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1331591
Male Wi star rats (300-350g) were decapitated and the kidneys were rapidly removed. The kidneys were minced in ice-cold 50 mM Tris-HCI, 5 mM EDTA (pH 7.7) and then homogenized by a polytron. The homogenate was filtered through 4 layers of silk gauze. and centrifuged at 40,000 X g for 13 min. The pellet was resuspended in 50 mM Tris-HCI, 25 mM NaCI buffer (pH 7.7), incubated for 30 min at 25°C, and recen trifuged as described above. The final pellet was resuspended in 50 mM Tris-HC1 buffer (pH 7.7) and used for the binding assay. Incubations were performed in duplicate at 25°C for
40 min in a total volume of 1 ml. The incubate consisted of 3H p-aminoclonidine (3H-PAC), a suspension of kidney membranes (approximately 0.55 mg/ml) and either buffer alone or buffer containing Tizanidine. Non-specific binding was defined by parallel incubations containing 10,uM phentolamine. In experiments using adrenaline, all samples contained ascortic acid in a final concentration of 0.01%. Incubations were terminated by vacuum filtration over Whatman GF/C filters by using a cell harvester. The filters were washed with ice-cold Tris-HCI; then the filter-bound radioactivity was determined using a scintillation counter (Aloka, Japan).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:17:18 GMT 2023
by
admin
on
Fri Dec 15 15:17:18 GMT 2023
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Record UNII |
6AI06C00GW
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
M03BX02
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WHO-VATC |
QM03BX02
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NCI_THESAURUS |
C29709
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LIVERTOX |
NBK548048
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NDF-RT |
N0000175554
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NDF-RT |
N0000009918
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2683
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C023754
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57258
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m10912
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7308
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TIZANIDINE
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DTXSID9023679
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4697
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C61976
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DB00697
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> SUBSTRATE |
IN MICROSOMES
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST |
SHORT-ACTING
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EXCRETED UNCHANGED |
URINE
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
PLASMA; URINE
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METABOLITE -> PARENT |
MINOR
PLASMA; URINE
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |