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Tizanidine HCl

Tizanidine HCl

Synopsis, Chemistry

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TABLET;ORAL - EQ 2MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - EQ 4MG BASE, CAPSULE;ORAL - EQ 2MG BASE, CAPSULE;ORAL - EQ 4MG BASE, CAPSULE;ORAL - EQ 6MG BASE

TABLET;ORAL - EQ 2MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
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Also known as: Tizanidine hcl, 64461-82-1, Zanaflex, Tizanidine (hydrochloride), 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride, Ds 103-282

Molecular Formula

C₉H₉Cl₂N₅S

Molecular Weight

290.17 g/mol

InChI Key

ZWUKMNZJRDGCTQ-UHFFFAOYSA-N

FDA UNII

B53E3NMY5C

Tizanidine Hydrochloride is the hydrochloride salt form of tizanidine, an imidazoline derivative structurally similar to clonidine and an adrenergic agonist with muscle relaxant property. Tizanidine stimulates alpha-2 adrenergic receptors in the central nervous system, thereby inhibiting presynaptic release of norepinephrine and increasing the inhibitory effect on alpha motor neurons and motor reflexes. Tizanidine exerts some activity at the postsynaptic excitatory amino acid receptors and imidazoline receptors which may contribute to the overall reduction in facilitation of spinal motor neurons. Overall, tizanidine hydrochloride causes muscle relaxation, reduces spasticity and antinociceptive effects.

1 2D Structure

Tizanidine HCl

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine;hydrochloride

2.1.2 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

2.1.3 InChI Key

ZWUKMNZJRDGCTQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN=C(N1)NC2=C(C=CC3=NSN=C32)Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

B53E3NMY5C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-chloro-4-(2-imidazolin-2-yl-amino)-2,1,3-benzothiadiazole

2. Ds 103-282

3. Sirdalud

4. Tizanidine

5. Tizanidine Monohydrochloride

6. Zanaflex

2.3.2 Depositor-Supplied Synonyms

1. Tizanidine Hcl

2. 64461-82-1

3. Zanaflex

4. Tizanidine (hydrochloride)

5. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine Hydrochloride

6. Ds 103-282

7. An021

8. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)benzo[c][1,2,5]thiadiazol-4-amine Hydrochloride

9. B53e3nmy5c

10. Tizanidine (as Hydrochloride)

11. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole Monohydrochloride

12. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine;hydrochloride

13. Ds-103-282

14. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole Hydrochloride

15. An-021

16. 64461-82-1 (hcl)

17. 2,1,3-benzothiadiazol-4-amine, 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-, Monohydrochloride

18. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine Hydrochloride

19. Smr000499584

20. Unii-b53e3nmy5c

21. Sr-01000765392

22. Tizanidine * Hcl

23. Zanaflex (tn)

24. Mfcd00798231

25. Tizanidine Hydrochloride [usan:usp:jan]

26. 5-iodoisoquinolin-8-ol

27. Schembl41199

28. Mls001076686

29. Mls001306412

30. Mls001333593

31. Chebi:9609

32. Tizanidine Hydrochloride- Bio-x

33. Chembl1200329

34. Dtxsid9046990

35. Ds-103282 Ch

36. Hy-b0194a

37. An-021a

38. Nvd-422

39. Amy18121

40. Bcp28540

41. Tox21_501114

42. S1437

43. Tizanidine Hydrochloride [mi]

44. Tizanidine Hydrochloride (jp17/usp)

45. Tizanidine Hydrochloride [jan]

46. Akos005267234

47. Brn0618691

48. Ccg-220602

49. Ccg-222418

50. Ks-1120

51. Lp01114

52. Nc00654

53. Tizanidine Hydrochloride [usan]

54. Tizanidine Hydrochloride [mart.]

55. Tizanidine Hydrochloride [vandf]

56. Ncgc00261799-01

57. Tizanidine Hydrochloride [who-dd]

58. Ac-22546

59. Bt164478

60. Db-011661

61. Ds-103282

62. Ds103-282

63. Ft-0656022

64. Sw199068-2

65. T2527

66. En300-49853

67. Tizanidine Hydrochloride [orange Book]

68. D00776

69. D70434

70. Tizanidine Hydrochloride [ep Monograph]

71. Tizanidine Hydrochloride [usp Impurity]

72. Tizanidine Hydrochloride [usp Monograph]

73. Tizanidine Hydrochloride, >=98% (hplc), Powder

74. Sr-01000765392-4

75. Q27274381

76. Tizanidine Hydrochloride 100 Microg/ml In Acetonitrile

77. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazolehydrochloride

78. Tizanidine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

79. (5-chloro-2,1,3-benzothiadiazol-4-yl)-(4,5-dihydro-1h-imidazol-2-yl)azanium;chloride

80. 5-(chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine Hydrochloride

81. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole Monohydrochloride.

82. 5-chloro-4-[(4,5-dihydro-1h-imidazol-2-yl)amino]-2,1,3-benzothiadiazole Hydrochloride

83. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3benzothiadiazole-4-amine Hydrochloride

84. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)benzo[c][1,2,5]thiadiazol-4-aminehydrochloride

85. Tizanidine Hydrochloride, 500 Mug/ml In Methanol, Certified Reference Material

86. Tizanidine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₉H₉Cl₂N₅S
Molecular Weight	290.17 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	288.9955719 g/mol
Monoisotopic Mass	288.9955719 g/mol
Topological Polar Surface Area	90.4 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	300
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Tizanidine hydrochloride
PubMed Health	Tizanidine (By mouth)
Drug Classes	Skeletal Muscle Relaxant, Centrally Acting
Drug Label	Zanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
Active Ingredient	Tizanidine hydrochloride
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 4mg base; eq 2mg base; eq 6mg base
Market Status	Prescription
Company	Corepharma; Mylan Pharms; Teva; Apotex; Sun Pharm Inds; Prosam Labs; Sandoz; Dr Reddys Labs; Mylan; Unichem Labs

2 of 4
Drug Name	Zanaflex
Drug Label	Zanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
Active Ingredient	Tizanidine hydrochloride
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 4mg base; eq 2mg base; eq 6mg base
Market Status	Prescription
Company	Acorda

3 of 4
Drug Name	Tizanidine hydrochloride
PubMed Health	Tizanidine (By mouth)
Drug Classes	Skeletal Muscle Relaxant, Centrally Acting
Drug Label	Zanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
Active Ingredient	Tizanidine hydrochloride
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 4mg base; eq 2mg base; eq 6mg base
Market Status	Prescription
Company	Corepharma; Mylan Pharms; Teva; Apotex; Sun Pharm Inds; Prosam Labs; Sandoz; Dr Reddys Labs; Mylan; Unichem Labs

4 of 4
Drug Name	Zanaflex
Drug Label	Zanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
Active Ingredient	Tizanidine hydrochloride
Dosage Form	Tablet; Capsule
Route	Oral
Strength	eq 4mg base; eq 2mg base; eq 6mg base
Market Status	Prescription
Company	Acorda

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Muscle Relaxants, Central

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)

Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

Adrenergic alpha-2 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Agonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Central alpha-2 Adrenergic Agonist [EPC]; Adrenergic alpha2-Agonists [MoA]