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Tizanidine

Tizanidine Structure
CAS No.
51322-75-9
Chemical Name:
Tizanidine
Synonyms
AB-021;C07452;TERNELIN;SIRDALUD;ZANAFLEX;DS-103-282;TIZANIDINE;TIZANIDINE HCL;Tizanidine USP/EP/BP;TIZANIDINE HCL 2% GRANULES
CBNumber:
CB9670538
Molecular Formula:
C9H8ClN5S
Molecular Weight:
253.71
MOL File:
51322-75-9.mol
Modify Date:
2023/9/4 15:51:00

Tizanidine Properties

Melting point 221-223°
Boiling point 391.2±52.0 °C(Predicted)
Density 1.82±0.1 g/cm3(Predicted)
storage temp. Store at -20°C
solubility H2O: ~29 mg/mL
form solid
pka 7.48±0.10(Predicted)
color white
CAS DataBase Reference 51322-75-9(CAS DataBase Reference)
NIST Chemistry Reference Tizanidine(51322-75-9)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS08,GHS07
Signal word  Warning
Hazard statements  H361-H302+H332
Precautionary statements  P201-P202-P281-P308+P313-P405-P501
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  26-36
WGK Germany  3
RTECS  DK9910000
Toxicity LD50 orally in mice: 235 mg/kg (Sayers)

Tizanidine Chemical Properties,Uses,Production

Description

Tizanidine is a centrally-acting muscle relaxant useful in the treatment of muscle spasms and a variety of spastic conditions.

Uses

Labeled Tizanidine, intended for use as an internal standard for the quantification of Tizanidine by GC- or LC-mass spectrometry.

Definition

ChEBI: 2,1,3-Benzothiadiazole substituted at C-4 by a Delta1-imidazolin-2-ylamino group and at C-4 by a chloro group. It is an agonist at alpha2-adrenergic receptor sites.

Mechanism of action

Tizanidine is a centrally active muscle relaxant analogue of clonidine that is approved for use in reducing spasticity associated with cerebral or spinal cord injury. Its mechanism of action for reducing spasticity suggests presynaptic inhibition of motor neurons at the α2-adrenergic receptor sites, reducing the release of excitatory amino acids and inhibiting facilitatory ceruleospinal pathways, thus resulting in a reduction in spasticity. Tizanidine only has a small fraction of the antihypertensive action of clonidine, presumably because of action at a selective subgroup of α2C-adrenoceptors, which appear to be responsible for the analgesic and antispasmodic activity of imidazoline α2-agonists(20).

Clinical Use

Tizanidine is a centrally acting adrenergic α2 receptor agonist used to treat chronic muscle spasticity conditions, such as multiple sclerosis.

Side effects

Postulated mechanisms include α2 receptor-mediated decreased release of norepinephrine and serotonin from spinal interneurons. Tizanidine is structurally related to the α2 agonist clonidine that is used to treat hypertension; however, the blood pressure–lowering potency of tizanidine is approximately 10 to 20% that of clonidine. Nevertheless, patients may experience hypotension with tizanidine, together with muscle weakness, that may result in dizziness and falls in mobile patients. Tizanidine is rapidly and almost completely absorbed from the gastrointestinal tract; however, the estimated bioavailability is only 10 to 15% because of extensive first-pass metabolism, mainly by CYP1A2, which results in oxidative degradation of the imidazoline ring and hydroxylation of the aromatic system. Elevated liver enzyme values are not frequent with tizanidine use. Hepatic injury and death because of liver failure have been reported, however, and this complication should be considered in view of its marginal antispasmodic efficacy. Other frequently reported side effects of tizanidine are drowsiness and dry mouth. Clonidine also has been used to treat spasticity; however, even less high-quality clinical study data are available for this agent.

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3-benzothiadiazole,5-chloro-4-(2-imidazolin-2-ylamino)-1 3-benzothiadiazole-4-amine,5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-1 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole 5-CHLORO-N-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-2,1,3-BENZOTHIADIAZOLE-4-AMINE HYDROCHLORIDE 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine (5-CHLORO-BENZO[1,2,5]THIADIAZOL-4-YL)-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-AMINE AB-021 DS-103-282 SIRDALUD TERNELIN TIZANIDINE TIZANIDINE HCL 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-8-thia-7,9-diazabicyclo[4.3.0]nona-2,4,6,9-tetraen-5-amine ZANAFLEX 5-Chloro-4-(2-imidazolin-2-ylamino)benzo-2,1,3-thiadiazole 5-CHLORO-N-(4,5-DIHYDR-1H-IMIDAZOL-2-YL)-2,1,3-BENZOTHIADIAZOLE-4-AMINE 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine 2,1,3-Benzothiadiazole, 5-chloro-4-(2-imidazolin-2-ylamino)- 2,1,3-Benzothiadiazole-4-amine, 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)- C07452 2,1,3-Benzothiadiazol-4-aMine, 5-chloro-N-(4,5-dihydro-1H-iMidazol-2-yl)- 5-chloro-N-(4,5-dihydro-1H-iMidazol-2-yl)benzo[c][1,2,5]thiadiazol-4-aMine hydrochloride Tizanidine USP/EP/BP TizanidineQ: What is Tizanidine Q: What is the CAS Number of Tizanidine Q: What is the storage condition of Tizanidine Q: What are the applications of Tizanidine TIZANIDINE HCL 2% GRANULES 51322-75-9 C9H8ClN5S C9H8CIN5SHCI Tizanidine