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Rizatriptan (benzoate)

Rizatriptan (benzoate)

Synopsis, Chemistry

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FILM;ORAL - EQ 10MG BASE, TABLET;ORAL - EQ 10MG BASE, TABLET;ORAL - EQ 5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET, ORALLY DISINTEGRATING;ORAL - EQ 10MG BASE, TABLET, ORALLY DISINTEGRATING;ORAL - EQ 5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

FILM;ORAL - EQ 10MG BASE
TABLET;ORAL - EQ 10MG BASE
TABLET;ORAL - EQ 5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET, ORALLY DISINTEGRATING;ORAL - EQ 10MG BASE
TABLET, ORALLY DISINTEGRATING;ORAL - EQ 5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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Also known as: 145202-66-0, Maxalt, Rizatriptan (benzoate), Maxalt-mlt, Mk 462, Mk-462

Molecular Formula

C₂₂H₂₅N₅O₂

Molecular Weight

391.5 g/mol

InChI Key

JPRXYLQNJJVCMZ-UHFFFAOYSA-N

FDA UNII

WR978S7QHH

Rizatriptan Benzoate is the benzoate salt form of rizatriptan, a member of the triptan class agents with anti-migraine property. Rizatriptan benzoate selectively binds to and activates serotonin (5-HT) 1B receptors expressed in intracranial arteries, and to 5-HT 1D receptors located on peripheral trigeminal sensory nerve terminals in the meninges and central terminals in brain stem sensory nuclei. Receptor binding results in constriction of cranial vessels and inhibition of nociceptive transmission, thereby providing relief of migraine headaches. Rizatriptan benzoate may also relief migraine headaches by inhibition of pro-inflammatory neuropeptide release.

1 2D Structure

rizatriptan, benzoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzoic acid;N,N-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine

2.1.2 InChI

InChI=1S/C15H19N5.C7H6O2/c1-19(2)6-5-13-8-17-15-4-3-12(7-14(13)15)9-20-11-16-10-18-20;8-7(9)6-4-2-1-3-5-6/h3-4,7-8,10-11,17H,5-6,9H2,1-2H3;1-5H,(H,8,9)

2.1.3 InChI Key

JPRXYLQNJJVCMZ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCC1=CNC2=C1C=C(C=C2)CN3C=NC=N3.C1=CC=C(C=C1)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

WR978S7QHH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. L 705,126

2. L 705126

3. L-705,126

4. L-705126

5. Maxalt

6. Mk 0462

7. Mk 462

8. Mk-0462

9. Mk-462

10. N,n-dimethyl-2-(5-(1,2,4-triazol-1-ylmethyl)-1h-indole-3-yl)ethylamine

11. Rizatriptan

2.3.2 Depositor-Supplied Synonyms

1. 145202-66-0

2. Maxalt

3. Rizatriptan (benzoate)

4. Maxalt-mlt

5. Mk 462

6. Mk-462

7. Mk-0462

8. 2-(5-((1h-1,2,4-triazol-1-yl)methyl)-1h-indol-3-yl)-n,n-dimethylethanamine Benzoate

9. Nsc-758919

10. Wr978s7qhh

11. Rizatriptan Benzoate (maxalt)

12. N,n-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethylamine Benzoate

13. 3-(2-(dimethylamino)ethyl)-5-(1h-1,2,4-triazol-1-ylmethyl)indole Monobenzoate

14. 1h-indole-3-ethanamine, N,n-dimethyl-5-(1h-1,2,4-triazol-1-ylmethyl)-, Monobenzoate

15. 2-(5-((1h-1,2,4-triazol-1-yl)methyl)-1h-indol-3-yl)-n,n-dimethylethan-1-amine Benzoate

16. Benzoic Acid;n,n-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethanamine

17. Rizatriptanbenzoate

18. N,n-dimethyl-5-(1h-1,2,4-triazol-1-ylmethyl)-1h-indole-3-ethanamine Benzoate

19. Rizatriptan Benzoate [usan]

20. Mk 0462

21. Unii-wr978s7qhh

22. L 705126

23. L 705,126

24. L-705,126

25. Rizatriptan Benzoate [usan:usp]

26. Rizatrimptan Benzoate

27. Rizatriptane Benzoate

28. Rizatriptan, Benzoate

29. Mk-462 Benzoate

30. Schembl41226

31. Mls001424197

32. Chebi:8875

33. Rizatriptan Benzoate Salt

34. Chembl1201032

35. Rizatriptan Benzoate (jan/usp)

36. Amy8935

37. Dtxsid20162937

38. Rhb-103

39. Rizatriptan Benzoate [mi]

40. Hms2051b16

41. Hms2093k08

42. Hms2235m18

43. Hms3369i15

44. Hms3393b16

45. Hms3655k09

46. Hms3715d08

47. Hms3884k21

48. Pharmakon1600-01505189

49. Rizatriptan Benzoate [jan]

50. Act04340

51. Bcp02149

52. Hy-b0206

53. Int-0008

54. Rizatriptan Benzoate [vandf]

55. Ac-734

56. Mfcd00866224

57. Nsc758919

58. Rizatriptan Benzoate [mart.]

59. Rizatriptan Benzoate [usp-rs]

60. Rizatriptan Benzoate [who-dd]

61. Akos015855933

62. Ab07521

63. Ccg-101039

64. Ks-1189

65. Nc00289

66. Nsc 758919

67. Rizatriptan Benzoate [orange Book]

68. Smr000525252

69. Rizatriptan Benzoate [ep Monograph]

70. Db-015783

71. Rizatriptan Benzoate [usp Monograph]

72. Rizatriptan Benzoate Salt, >=98% (hplc)

73. Ft-0631171

74. R0107

75. R0181

76. S1607

77. Sw197669-2

78. D00675

79. 202r660

80. A808337

81. Sr-01000763588

82. J-008071

83. J-524222

84. Sr-01000763588-3

85. Q27292788

86. Rizatriptan Benzoate, European Pharmacopoeia (ep) Reference Standard

87. Rizatriptan Benzoate, United States Pharmacopeia (usp) Reference Standard

88. Dimethyl-[2-(5-[1,2,4]triazol-1-ylmethyl-1h-indol-3-yl)-ethyl]-amine Benzoate

89. N,n-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethanamine Benzoate

90. Rizatriptan For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₅N₅O₂
Molecular Weight	391.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Exact Mass	391.20082506 g/mol
Monoisotopic Mass	391.20082506 g/mol
Topological Polar Surface Area	87 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	412
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	Maxalt
PubMed Health	Rizatriptan (By mouth)
Drug Classes	Antimigraine
Drug Label	MAXALTCOPYRIGHT 1998, 2006 Merck Sharp & Dohme Corp., a subsidiary of Merck & Co., Inc.All rights reserved contains rizatriptan benzoate, a selective 5-hydroxytryptamine1B/1D (5-HT1B/1D) receptor agonist.Rizatriptan benzoate is described chemical
Active Ingredient	Rizatriptan benzoate
Dosage Form	Tablet
Route	Oral
Strength	eq 5mg base; eq 10mg base
Market Status	Prescription
Company	Merck

2 of 4
Drug Name	Rizatriptan benzoate
Drug Label	MAXALTCOPYRIGHT 1998, 2006 Merck Sharp & Dohme Corp., a subsidiary of Merck & Co., Inc.All rights reserved contains rizatriptan benzoate, a selective 5-hydroxytryptamine1B/1D (5-HT1B/1D) receptor agonist.Rizatriptan benzoate is described chemical
Active Ingredient	Rizatriptan benzoate
Dosage Form	Tablet; Tablet, orally disintegrating
Route	Oral
Strength	eq 5mg base; eq 10mg base
Market Status	Prescription
Company	Mylan Pharms; Apotex; Aurobindo Pharma; Natco Pharma; Sandoz; Invagen Pharms; Cipla; Sun Pharma Global; Glenmark Generics; Emcure Pharms; Teva Pharms; Macleods Pharms

3 of 4
Drug Name	Maxalt
PubMed Health	Rizatriptan (By mouth)
Drug Classes	Antimigraine
Drug Label	MAXALTCOPYRIGHT 1998, 2006 Merck Sharp & Dohme Corp., a subsidiary of Merck & Co., Inc.All rights reserved contains rizatriptan benzoate, a selective 5-hydroxytryptamine1B/1D (5-HT1B/1D) receptor agonist.Rizatriptan benzoate is described chemical
Active Ingredient	Rizatriptan benzoate
Dosage Form	Tablet
Route	Oral
Strength	eq 5mg base; eq 10mg base
Market Status	Prescription
Company	Merck

4 of 4
Drug Name	Rizatriptan benzoate
Drug Label	MAXALTCOPYRIGHT 1998, 2006 Merck Sharp & Dohme Corp., a subsidiary of Merck & Co., Inc.All rights reserved contains rizatriptan benzoate, a selective 5-hydroxytryptamine1B/1D (5-HT1B/1D) receptor agonist.Rizatriptan benzoate is described chemical
Active Ingredient	Rizatriptan benzoate
Dosage Form	Tablet; Tablet, orally disintegrating
Route	Oral
Strength	eq 5mg base; eq 10mg base
Market Status	Prescription
Company	Mylan Pharms; Apotex; Aurobindo Pharma; Natco Pharma; Sandoz; Invagen Pharms; Cipla; Sun Pharma Global; Glenmark Generics; Emcure Pharms; Teva Pharms; Macleods Pharms

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Serotonin Receptor Agonists

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]