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Benazepril Hydrochloride

Synopsis, Chemistry

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2 Suppliers

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163 Dossiers, 150 FDA Orange Book, 6 Canada, 7 Listed Dossiers

DRUG PRODUCT COMPOSITION

TABLET;ORAL - 10MG, TABLET;ORAL - 20MG, TABLET;ORAL - 40MG, TABLET;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, CAPSULE;ORAL - EQ 10MG BASE;20MG, CAPSULE;ORAL - EQ 10MG BASE;40MG, CAPSULE;ORAL - EQ 2.5MG BASE;10MG, CAPSULE;ORAL - EQ 5MG BASE;10MG, CAPSULE;ORAL - EQ 5MG BASE;20MG, CAPSULE;ORAL - EQ 5MG BASE;40MG

TABLET;ORAL - 10MG
TABLET;ORAL - 20MG
TABLET;ORAL - 40MG
TABLET;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
CAPSULE;ORAL - EQ 10MG BASE;20MG
CAPSULE;ORAL - EQ 10MG BASE;40MG
CAPSULE;ORAL - EQ 2.5MG BASE;10MG
CAPSULE;ORAL - EQ 5MG BASE;10MG
CAPSULE;ORAL - EQ 5MG BASE;20MG
CAPSULE;ORAL - EQ 5MG BASE;40MG

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2 APIs

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Europe

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U.S. Medicaid

235.00

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SERVICES

Also known as: 86541-74-4, Benazepril hcl, Lotensin, Cibacen, Cibacene, Briem

Molecular Formula

C₂₄H₂₉ClN₂O₅

Molecular Weight

460.9 g/mol

InChI Key

VPSRQEHTHIMDQM-FKLPMGAJSA-N

FDA UNII

N1SN99T69T

Benazepril Hydrochloride is the hydrochloride salt of benazepril, a carboxyl-containing angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. As a prodrug, benazepril is metabolized to its active form benazeprilat. Benazeprilat competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II, resulting in vasodilation. Benazeprilat also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.

1 2D Structure

Benazepril Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(3S)-3-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3H-1-benzazepin-1-yl]acetic acid;hydrochloride

2.1.2 InChI

InChI=1S/C24H28N2O5.ClH/c1-2-31-24(30)20(14-12-17-8-4-3-5-9-17)25-19-15-13-18-10-6-7-11-21(18)26(23(19)29)16-22(27)28;/h3-11,19-20,25H,2,12-16H2,1H3,(H,27,28);1H/t19-,20-;/m0./s1

2.1.3 InChI Key

VPSRQEHTHIMDQM-FKLPMGAJSA-N

2.1.4 Canonical SMILES

CCOC(=O)C(CCC1=CC=CC=C1)NC2CCC3=CC=CC=C3N(C2=O)CC(=O)O.Cl

2.1.5 Isomeric SMILES

CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H]2CCC3=CC=CC=C3N(C2=O)CC(=O)O.Cl

2.2 Other Identifiers

2.2.1 UNII

N1SN99T69T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Benazapril

2. Benazepril

3. Benzazepril

4. Briem

5. Cgs-14824-a

6. Cgs-14824a

7. Cibacne

8. Cibacen

9. Labopal

10. Lotensin

2.3.2 Depositor-Supplied Synonyms

1. 86541-74-4

2. Benazepril Hcl

3. Lotensin

4. Cibacen

5. Cibacene

6. Briem

7. Tensanil

8. Zinadril

9. Cibace

10. Labopol

11. Cgs 14824a Hcl

12. Benazepril (hydrochloride)

13. Cgs 14824a

14. Nsc-758920

15. Cgs-14824a Hcl

16. Chebi:3012

17. N1sn99t69t

18. (3s)-3-(((1s)-1-carboxy-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-1h-1-benzazepine-1-acetic Acid, 3-ethyl Ester, Monohydrochloride

19. (3s)-3-[[(1s)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-2,3,4,5-tetrahydro-2-oxo-1h-1-benzazepine-1-acetic Acid Hydrochloride

20. 86541-74-4 (hcl)

21. Cibacen Chf

22. Dsstox_cid_25922

23. Dsstox_rid_81225

24. Dsstox_gsid_45922

25. 1h-1-benzazepine-1-acetic Acid, 3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2,3,4,5-tetrahydro-2-oxo-, Monohydrochloride, (s-(r*,r*))-

26. 2-((s)-3-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino)-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b]azepin-1-yl)acetic Acid Hydrochloride

27. 2-[(3s)-3-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic Acid;hydrochloride

28. 2-[(3s)-3-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-1-yl]acetic Acid Hydrochloride

29. Smr000469199

30. Cas-86541-74-4

31. Mfcd00895734

32. Unii-n1sn99t69t

33. Ncgc00095132-01

34. Lotensin (tn)

35. 2-((s)-3-((s)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)-2-oxo-2,3,4,5-tetrahydro-1h-benzo[b]azepin-1-yl)acetic Acid Hydrochloride

36. Benazeprilhydrochloride

37. Benazepril Hydrochloride [usan:usp:jan]

38. Benazepril Monohydrochloride

39. Chembl1694

40. Schembl42194

41. Benazepril Hydrochloride,(s)

42. Mls001076668

43. Mls001333171

44. Mls001333172

45. Mls001401429

46. Spectrum1505200

47. Benazepril Hydrochloride- Bio-x

48. Dtxsid9045922

49. Benazepril For System Suitability

50. Hy-b0093a

51. Bcpp000350

52. Hms1922l07

53. Pharmakon1600-01505200

54. Twt-8154

55. Benazepril Hydrochloride (jan/usp)

56. Tox21_111441

57. Benazepril Hydrochloride [mi]

58. Ccg-39520

59. Nsc758920

60. S1284

61. Benazepril Hydrochloride [jan]

62. Akos015888536

63. Tox21_111441_1

64. Bcp9000387

65. Benazepril Hydrochloride [hsdb]

66. Benazepril Hydrochloride [usan]

67. Cs-1796

68. Ks-1397

69. Nc00211

70. Nsc 758920

71. Benazepril Hydrochloride [mart.]

72. Benazepril Hydrochloride [usp-rs]

73. Benazepril Hydrochloride [who-dd]

74. Ncgc00165740-05

75. (3s)-3-[(1s)-1-ethoxycarbonyl-3-phenylpropyl]amino-2,3,4,5-tetrahydro-2-oxo-1h-1-benzazepine-1-acetic Acid Hydrochloride

76. 1h-1-benzazepine-1-acetic Acid, 2,3,4,5-tetrahydro-3-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-2-oxo-, Monohydrochloride, (s-(r*,r*))-

77. Bb164237

78. B3611

79. Sw197591-3

80. Benazepril Hydrochloride [ep Impurity]

81. Benazepril Hydrochloride [orange Book]

82. Benazepril Hydrochloride [usp Impurity]

83. Benazepril Hydrochloride [usp Monograph]

84. C07701

85. D00620

86. Lotrel Component Benazepril Hydrochloride

87. Benazepril Hydrochloride, >=98% (hplc), Solid

88. A841712

89. Benazepril Hydrochloride Component Cardalis

90. Benazepril Hydrochloride Component Of Lotrel

91. Cardalis Component Benazepril Hydrochloride

92. Sr-01000762893

93. Sr-01000762893-3

94. Benazepril Hydrochloride [ema Epar Veterinary]

95. Fortekor Plus Component Benazepril Hydrochloride

96. Lotensin Hct Component Benazepril Hydrochloride

97. Q27105927

98. Benazepril Hydrochloride Component Of Lotensin Hct

99. Benazepril Hydrochloride Component Of Fortekor Plus

100. Benazepril Hydrochloride, Vetranal(tm), Analytical Standard

101. Benazepril Hydrochloride, European Pharmacopoeia (ep) Reference Standard

102. Benazepril For System Suitability, European Pharmacopoeia (ep) Reference Standard

103. Benazepril Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

104. Benazepril Hydrochloride, United States Pharmacopeia (usp) Reference Standard

105. [(3s)-3-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-1-yl]acetic Acid Hydrochloride

106. 2-[(3s)-3-[[(1s)-1-ethoxycarbonyl-3-phenyl-propyl]amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetic Acid Hydrochloride;benazepril Hydrochloride

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₉ClN₂O₅
Molecular Weight	460.9 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	10
Exact Mass	460.1764997 g/mol
Monoisotopic Mass	460.1764997 g/mol
Topological Polar Surface Area	95.9 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	619
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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	Benazepril hydrochloride
PubMed Health	Benazepril (By mouth)
Drug Classes	Antihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug Label	Benazepril hydrochloride is a white to off-white crystalline powder, soluble (> 100 mg/mL) in water, in ethanol, and in methanol. BenazeprilC24H28N2O5HCl M.W. 460.96Benazeprilat, the active metabolite of benazepril, is a non-sulfhydryl angiotensin-co..
Active Ingredient	Benazepril hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg; 40mg; 20mg
Market Status	Prescription
Company	Ranbaxy; Ivax Sub Teva Pharms; Actavis Labs Fl; Teva; Apotex; Aurobindo Pharma; Zydus Pharms Usa; Biokey; Sandoz; Prinston; Mylan

2 of 4
Drug Name	Lotensin
Drug Label	Benazepril hydrochloride is a white to off-white crystalline powder, soluble (>100 mg/mL) in water, in ethanol, and in methanol. Its chemical name is benazepril 3-[[1-(ethoxy-carbonyl)-3-phenyl-(1S)-propyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-(3S)-be..
Active Ingredient	Benazepril hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg; 40mg; 20mg
Market Status	Prescription
Company	Us Pharms Holdings I

3 of 4
Drug Name	Benazepril hydrochloride
PubMed Health	Benazepril (By mouth)
Drug Classes	Antihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug Label	Benazepril hydrochloride is a white to off-white crystalline powder, soluble (> 100 mg/mL) in water, in ethanol, and in methanol. BenazeprilC24H28N2O5HCl M.W. 460.96Benazeprilat, the active metabolite of benazepril, is a non-sulfhydryl angiotensin-co..
Active Ingredient	Benazepril hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg; 40mg; 20mg
Market Status	Prescription
Company	Ranbaxy; Ivax Sub Teva Pharms; Actavis Labs Fl; Teva; Apotex; Aurobindo Pharma; Zydus Pharms Usa; Biokey; Sandoz; Prinston; Mylan

4 of 4
Drug Name	Lotensin
Drug Label	Benazepril hydrochloride is a white to off-white crystalline powder, soluble (>100 mg/mL) in water, in ethanol, and in methanol. Its chemical name is benazepril 3-[[1-(ethoxy-carbonyl)-3-phenyl-(1S)-propyl]amino]-2,3,4,5-tetrahydro-2-oxo-1H-1-(3S)-be..
Active Ingredient	Benazepril hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	5mg; 10mg; 40mg; 20mg
Market Status	Prescription
Company	Us Pharms Holdings I

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Angiotensin-Converting Enzyme Inhibitors

A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Angiotensin-converting Enzyme Inhibitors [MoA]; Decreased Blood Pressure [PE]; Angiotensin Converting Enzyme Inhibitor [EPC]