| Identification | More | [Name]
Tizanidine hydrochloride | [CAS]
64461-82-1 | [Synonyms]
5-CHLORO-N-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-2,1,3-BENZOTHIADIAZOL-4-AMINE HYDROCHLORIDE
5-CHLORO-N-(4,5-DIHYDRO-1H-IMIDAZOL-2-YL)-2,1,3-BENZOTHIADIAZOLE-4-AMINE HYDROCHLORIDE
AB-021
DS-103-282
SIRDALUD
TERNELIN
TIZANIDINE HCL
TIZANIDINE HYDROCHLORIDE
ZANAFLEX
1,3-benzothiadiazol-4-amine,5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-mono
5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazolehydrochloride
TizanidineHydrochloride(Patent)
5-Chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine, Hydrochloride, AB-021, DS-103-282, Sirdalud, Ternelin, Zanaflex
5-Chloro-4-[(4,5-dihydro-1H-imidazol-2-yl)amino]-2,1,3-benzothiadiazole Hydrochloride
Astonelin
Enchinin
Gibonz
Zanpeak | [Molecular Formula]
C9H9Cl2N5S | [MDL Number]
MFCD00798231 | [Molecular Weight]
290.17 | [MOL File]
64461-82-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
280 °C | [Fp ]
9℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
H2O: ~29 mg/mL
| [form ]
solid
| [color ]
white
| [Usage]
A muscle relaxant | [Merck ]
9485 | [InChI]
InChI=1S/C9H8ClN5S.ClH/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);1H | [InChIKey]
ZWUKMNZJRDGCTQ-UHFFFAOYSA-N | [SMILES]
N1=C2C=CC(Cl)=C(NC3NCCN=3)C2=NS1.[H]Cl | [CAS DataBase Reference]
64461-82-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [RIDADR ]
UN1230 - class 3 - PG 2 - Methanol, solution | [WGK Germany ]
3
| [RTECS ]
DK9910000
| [HS Code ]
2934990002 |
| Questions And Answer | Back Directory | [Description]
As an adrenergic agonist with muscle relaxant activity, tizanidine hydrochloride belongs to the hydrochloride salt form of tizanidine, which is commonly used in the treatment of spasticity, a condition where muscles in human body spasm, cramp, or become tight induced by a variety of medical problems such as multiple sclerosis, spinal cord injury, Lou Gehrig's disease, spastic diplegia, back pain or certain other injuries to the spine or central nervous system. Besides, as a sleep aid and an anticonvulsant, tizanidine hydrochloride has off-label usage for migraine headaches and is effective for some symptoms of fibromyalgia.
As a short-acting muscle relaxer, the antinociceptive effect of tizanidine hydrochloride functions by blocking excess nerve impulses (pain sensations) of the nerve cells that are sent to the brain and control muscle movement, ultimately resulting in muscle relaxation and spasticity alleviation.
| [References]
https://en.wikipedia.org/wiki/Tizanidine
http://www.webmd.com/drugs/2/drug-1024/tizanidine-oral/details
http://bodyandhealth.canada.com/drug/getdrug/pal-tizanidine
https://pubchem.ncbi.nlm.nih.gov/compound/114869#section=Top
https://www.drugs.com/tizanidine.html
|
| Hazard Information | Back Directory | [Chemical Properties]
Off-White to pale Yellow Solid | [Originator]
Nimzox,Rapross Pharmaceuticals
Pvt. Ltd.,India | [Uses]
An α2-adrenergic agonist; centrally active myotonolytic. A muscle relaxant (skeletal). | [Uses]
Anticoagulant | [Uses]
Tizanidine (Zanaflex) is a drug that is used as a muscle relaxant. It is a centrally acting α-2 adrenergic agonist. It is used to treat the spasms, cramping, and tightness of muscles caused by medical problems such as multiple sclerosis, spastic diplegia, | [Definition]
ChEBI: Tizanidine hydrochloride is a benzothiadiazole. | [Manufacturing Process]
14 ml of benzoyl chloride are added to a solution of 11.5 g of ammonium
thiocyanate in 150 ml of acetone in an ice bath and the mixture is then stirred
for 10 min. This solution is heated to the boil at reflux together with 19 g of
4-amino-5-chloro-2,1,3-benzothiadiazole. The solution is cooled to room
temperature and diluted with a 4-fold quantity of water. The precipitate is
filtered off and rapidly brought to a boil together with 150 ml of a 2 N
aqueous sodium hydroxide solution and kept at the boil for 5 min. The
solution is cooled to room temperature, is acidified weakly with glacial acetic
acid, the precipitate is filtered off, washed with ether and recrystallized from
methanol. The N-(5-chloro-2,1,3-benzothiadiazol-4-yl)thiourea, obtained and
this is boiled for 1 h together with 9 g of methyl iodide in 150 ml of methanol.
After concentrating by evaporation, crude S-methyl-N-(5-chloro-2,1,3-
benzothiadiazol-4-yl)isothiuronium iodide is obtained. 9.8 g of S-methyl-N-(5-
chloro-2,1,3-benzothiadiazol-4-yl)isothiuronium iodide are heated to the boil
at reflux for 1 h together with 50 ml of methanol and 1.8 ml of ethylene
diamine. The solvent is then removed by evaporation and the moist residue is
boiled at reflux for 1 h together with 20 ml of n-amyl alcohol. The mixture is
subsequently shaken with 50 ml of chloroform and 150 ml of water until all
the material is dissolved. 40 ml of a 2 N aqueous sodium hydroxide solution
are added to the aqueous phase and extraction is effected with 200 ml of
chloroform. The organic phase is dried and concentrated by evaporation. After
recrystallizing the residue from methanol with the addition of some active
charcoal, 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole, having a melting point of 221-223°C, is obtained.
The 4-(2-imidazolin-2-yl-amino)-5-chloro-2,1,3-benzothiadiazole hydrochloride
may be obtained by the teaction of 4-(2-imidazolin-2-yl-amino)-5-chloro-
2,1,3-benzothiadiazole with hydrochloric acid. | [Brand name]
Tizanidine is
INN and BAN. | [Therapeutic Function]
Muscle relaxant, Spasmolytic | [Biological Activity]
α 2 -adrenergic receptor agonist. Antinociceptive upon epidural administration in rats (IC 50 = 48 nM). Also binds to imidazoline receptor. | [storage]
Desiccate at RT |
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