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Chemistry

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Also known as: 168273-06-1, Acomplia, Zimulti, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-(piperidin-1-yl)-1h-pyrazole-3-carboxamide, Sr141716, Rimoslim

Molecular Formula

C₂₂H₂₁Cl₃N₄O

Molecular Weight

463.8 g/mol

InChI Key

JZCPYUJPEARBJL-UHFFFAOYSA-N

FDA UNII

RML78EN3XE

A pyrazole and piperidine derivative that acts as a selective cannabinoid type-1 receptor (CB1 RECEPTOR) antagonist. It inhibits the proliferation and maturation of ADIPOCYTES, improves lipid and glucose metabolism, and regulates food intake and energy balance. It is used in the management of OBESITY.

1 2D Structure

Rimonabant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide

2.1.2 InChI

InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)

2.1.3 InChI Key

JZCPYUJPEARBJL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(N(N=C1C(=O)NN2CCCCC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)Cl

2.2 Other Identifiers

2.2.1 UNII

RML78EN3XE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acomplia

2. N-(piperidin-1-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1h-pyrazole-3-carboxamide Hydrochloride

3. Rimonabant Hydrochloride

4. Sr 141716

5. Sr 141716a

6. Sr-141716a

7. Sr141716

8. Sr141716a

9. Zimulti

2.3.2 Depositor-Supplied Synonyms

1. 168273-06-1

2. Acomplia

3. Zimulti

4. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-(piperidin-1-yl)-1h-pyrazole-3-carboxamide

5. Sr141716

6. Rimoslim

7. Sr 141716

8. Sr141716a

9. Sr-141716a

10. A 281

11. Rimonabant Free Base

12. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-piperidin-1-ylpyrazole-3-carboxamide

13. Sr-141716

14. Rml78en3xe

15. Chembl111

16. Rimonabant (sr141716)

17. Chebi:34967

18. Ncgc00164572-01

19. Sr-14171

20. [3h]sr141716a

21. 158681-13-1 (hcl)

22. [3h]rimonabant

23. Dsstox_cid_26453

24. Dsstox_rid_81627

25. Dsstox_gsid_46453

26. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1h-pyrazole-3-carboxylic Acid Piperidin-1-ylamide

27. Acomplia (tn)

28. Rimonabant [inn]

29. Smr003500713

30. Cas-168273-06-1

31. Unii-rml78en3xe

32. Rimonabant (jan/usan/inn)

33. Rimonabant [usan:inn:jan]

34. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-1-piperidinyl-1h-pyrazole-3-carboxamide

35. Rimonabant- Bio-x

36. 1h-pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-1-piperidinyl-

37. Sr141,716a

38. Rimonabant [mi]

39. Rimonabant [jan]

40. 1h-pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-1-piperidinyl-, Monohydrochloride

41. Rimonabant - From Sample

42. Rimonabant [usan]

43. Rimonabant(sr141716)

44. Rimonabant [mart.]

45. 5-(p-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-piperidinopyrazole-3-carboxamide

46. Rimonabant [who-dd]

47. Schembl38637

48. Gtpl743

49. Mls004774043

50. Mls006011772

51. Rimonabant [ema Epar]

52. Dtxsid3046453

53. Bdbm21278

54. Ex-a688

55. Hms3604m05

56. Hms3657o15

57. Bcp07803

58. Zinc1540228

59. Tox21_112200

60. Ac-731

61. Bbl030198

62. Mfcd04034714

63. Nsc791533

64. S3021

65. Stk642500

66. Akos005266728

67. Tox21_112200_1

68. Am84578

69. Ccg-269385

70. Cs-0645

71. Db06155

72. Nsc-791533

73. Sb19549

74. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-(1-piperidyl)pyrazole-3-carboxamide

75. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-piperidino-1h-pyrazole-3-carboxamide

76. Ncgc00164572-02

77. As-37280

78. Br164345

79. Hy-14136

80. Ac-163720

81. Db-011649

82. B1429

83. Ft-0631194

84. R0205

85. Sw220167-1

86. 81r131

87. D05731

88. Ab01566860_01

89. A810956

90. L000572

91. Q412529

92. Sr-01000884001

93. J-010440

94. Sr-01000884001-1

95. (n-(piperidin-1-yl)-5-(4-chlorophenyl)-4-methyl-1h-pyrazole-3-carboxamide

96. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-(1-piperidinyl)-3-pyrazolecarboxamide

97. 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-piperidin-1-yl-pyrazole-3-carboxamide

98. N-piperidino-5-(4-chlorophenyl)-1(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carboxamide

99. N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazolecarboxamide

100. 1h-pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-n-1-piperidinyl-

101. 5-(4-chlorophenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1h-pyrazole-3-carboxylic Acid Piperidin-1-ylamide

102. Ay6

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₁Cl₃N₄O
Molecular Weight	463.8 g/mol
XLogP3	6.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	462.078094 g/mol
Monoisotopic Mass	462.078094 g/mol
Topological Polar Surface Area	50.2 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	583
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	1

4 Drug and Medication Information

4.1 Drug Indication

For use in conjunction with diet and exercise for patients with a body mass index greater than 30 kg/m², or patients wih a BMI greater than 27 kg/m² with associated risk factors, such as type 2 diabetes or dyslipidaemia.

As an adjunct to diet and exercise for the treatment of obese patients (BMI 30 kg/m2), or overweight patients (BMI 27 kg/m2) with associated risk factor(s), such as type 2 diabetes or dyslipidaemia (see section 5. 1).

5 Pharmacology and Biochemistry

5.1 Pharmacology

In the RIO-North America trial, 3040 patients were randomized to receive either placebo or one of two doses of rimonabant (5 mg or 20 mg per day). Patients taking 20 mg rimonabant had significant weigh loss, decrease in waist circumference, improved insulin sensitivity, and increases in HDL cholesterol, compared to patients on placebo.

5.2 MeSH Pharmacological Classification

Anti-Obesity Agents

Agents that increase energy expenditure and weight loss by neural and metabolic regulation. (See all compounds classified as Anti-Obesity Agents.)

Cannabinoid Receptor Antagonists

Compounds that inhibit or block the activity of CANNABINOID RECEPTORS. (See all compounds classified as Cannabinoid Receptor Antagonists.)

5.3 ATC Code

A08AX01

A - Alimentary tract and metabolism

A08 - Antiobesity preparations, excl. diet products

A08A - Antiobesity preparations, excl. diet products

A08AX - Other antiobesity drugs

A08AX01 - Rimonabant

5.4 Absorption, Distribution and Excretion

Absorption

Undetermined

5.5 Metabolism/Metabolites

Hepatic, CYP3A4 involved.

5.6 Biological Half-Life

6 to 9 days with normal BMI and 16 days if BMI is greater than 30

5.7 Mechanism of Action

Rimonabant is a specific CB1 cannabinoid receptor antagonist. There is considerable evidence that the endocannabinoid (endogenous cannabinoid) system plays a significant role in appetitive drive and associated behaviours. It is therefore reasonable to hypothesize that the attenuation of the activity of this system would have therapeutic benefit in treating disorders that might have a component of excess appetitive drive or over-activity of the endocannabinoid system, such as obesity, ethanol and other drug abuse, and a variety of central nervous system and other disorders.

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