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Quinapril hydrochloride
Also known as: 82586-55-8, Accupril, Quinapril hcl, Accuprin, Korec, Acequin
Molecular Formula
C25H31ClN2O5
Molecular Weight
475.0  g/mol
InChI Key
IBBLRJGOOANPTQ-JKVLGAQCSA-N
FDA UNII
33067B3N2M

A tetrahydroisoquinoline derivative and ANGIOTENSIN CONVERTING ENZYME inhibitor that is used in the treatment of HYPERTENSION and HEART FAILURE.
1 2D Structure

Quinapril hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid;hydrochloride
2.1.2 InChI
InChI=1S/C25H30N2O5.ClH/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30;/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30);1H/t17-,21-,22-;/m0./s1
2.1.3 InChI Key
IBBLRJGOOANPTQ-JKVLGAQCSA-N
2.1.4 Canonical SMILES
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC=CC=C3CC2C(=O)O.Cl
2.1.5 Isomeric SMILES
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC=CC=C3C[C@H]2C(=O)O.Cl
2.2 Other Identifiers
2.2.1 UNII
33067B3N2M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid

2. Accupril

3. Ci 906

4. Ci-906

5. Pd 109,452 2

6. Pd 109452 2

7. Pd 109452-2

8. Pd 1094522

9. Pd-109,452-2

10. Quinapril

2.3.2 Depositor-Supplied Synonyms

1. 82586-55-8

2. Accupril

3. Quinapril Hcl

4. Accuprin

5. Korec

6. Acequin

7. Quinazil

8. Hemokvin

9. Lidaltrin

10. Acuitel

11. Ectren

12. Conan

13. Quinapril (hydrochloride)

14. Accupro

15. Ci-906

16. Quinapril.hcl

17. Ci906

18. Ci 906

19. Quinaprilhydrochloride

20. Quinapril Hydrochloride

21. Nsc-758222

22. Chebi:8714

23. Quinapril Hydrochloride (accupril)

24. 33067b3n2m

25. (3s)-2-[(2s)-2-[[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1h-isoquinoline-3-carboxylic Acid;hydrochloride

26. (s)-2-(((s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-l-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Hydrochloride

27. (s)-2-((s)-n-((s)-1-carboxy-3-phenylpropyl)alanyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid, 1-ethyl Ester, Monohydrochloride

28. Accupron

29. Acuprel

30. Continucor

31. Koretic

32. Asig

33. Dsstox_cid_1221

34. Dsstox_rid_76019

35. Dsstox_gsid_21221

36. (s)-2-((s)-2-((s)-1-ethoxy-1-oxo-4-phenylbutan-2-ylamino)propanoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Hydrochloride

37. Cas-82586-55-8

38. Quinapril Hydrochloride [usan]

39. Hsdb 7046

40. Pd 109452-2

41. Unii-33067b3n2m

42. Quinapril N-oxide

43. Ncgc00094997-01

44. Accupril (tn)

45. Quinapril Hydrochloride [usan:usp]

46. Mfcd00889215

47. Quinapril Hydrochloride;

48. Schembl41404

49. Mls001076683

50. Quinapril Hydrochloride ,(s)

51. Spectrum1503076

52. Quinapril Hydrochloride- Bio-x

53. Quinapril For System Suitability

54. Chembl1201011

55. Dtxsid3021221

56. Quinapril For Peak Identification

57. Hms1922c15

58. Pharmakon1600-01503076

59. Tetrahydroisoquinoline-3-carboxylic

60. Hy-b0477

61. 2-ylamino)propanoyl)-1,2,3,4-

62. Quinapril Hydrochloride [mi]

63. Tox21_111381

64. Tox21_200390

65. Ccg-39543

66. Nsc758222

67. Quinapril Hydrochloride (jp17/usp)

68. Quinapril Hydrochloride [jan]

69. S2581

70. Quinapril Hydrochloride [hsdb]

71. Akos015888532

72. Pd-109452-2

73. Tox21_111381_1

74. Ac-1655

75. Nc00722

76. Nsc 758222

77. Quinapril Hydrochloride [mart.]

78. Quinapril Hydrochloride [vandf]

79. Quinapril Hydrochloride [usp-rs]

80. Quinapril Hydrochloride [who-dd]

81. Ncgc00167962-06

82. Ncgc00257944-01

83. (3s)-2-(n-{(1s)-1-[(ethyloxy)carbonyl]-3-phenylpropyl}-l-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Hydrochloride

84. (3s)-2-[(2s)-2-{[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Hydrochloride

85. 3-isoquinolinecarboxylic Acid, 1,2,3,4-tetrahydro-2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-, Monohydrochloride, (3s-(2(r*(r*)),3r*))-

86. 3-isoquinolinecarboxylic Acid, 2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-, Monohydrochloride, (3s-(2(r*(r*)),3r*))

87. As-14026

88. Bq164301

89. Smr000499582

90. Pd-109522

91. Pd109452-2

92. Quinapril Hydrochloride [orange Book]

93. Sw199393-2

94. Quinapril Hydrochloride [ep Monograph]

95. Quinapril Hydrochloride [usp Impurity]

96. C07340

97. D00459

98. F20594

99. Quinapril Hydrochloride [usp Monograph]

100. Quinapril Hydrochloride, >=98% (hplc), Solid

101. 586q558

102. A840381

103. Accuretic Component Quinapril Hydrochloride

104. Quinaretic Component Quinapril Hydrochloride

105. Sr-01000765404

106. Sr-01000765404-2

107. Q27108138

108. Quinapril Hydrochloride Component Of Accuretic

109. Quinapril Hydrochloride Component Of Quinaretic

110. (s)-2-((s)-2-((s)-1-ethoxy-1-oxo-4-phenylbutan-

111. Quinapril Hydrochloride, European Pharmacopoeia (ep) Reference Standard

112. Quinapril Hydrochloride, United States Pharmacopeia (usp) Reference Standard

113. Quinapril For Peak Identification, European Pharmacopoeia (ep) Reference Standard

114. Quinapril For System Suitability, European Pharmacopoeia (ep) Reference Standard

115. Quinapril Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

116. (3s)-2-{(2s)-2-[(1s)-1-ethoxycarbonyl-3-phenylpropylamino]propanoyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Hydrochloride

117. (3s)-2-{n-[(2s)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]-l-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic Acid Hydrochloride

118. 2-(2-((1-ethoxycarbonyl-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic Acid Monohydrochloride(3s-(2(r*(r*)),3r*)

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 475.0 g/mol
Molecular Formula C25H31ClN2O5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count10
Exact Mass474.1921498 g/mol
Monoisotopic Mass474.1921498 g/mol
Topological Polar Surface Area95.9 Ų
Heavy Atom Count33
Formal Charge0
Complexity648
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAccupril
PubMed HealthQuinapril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelACCUPRIL (quinapril hydrochloride) is the hydrochloride salt of quinapril, the ethyl ester of a non-sulfhydryl, angiotensin-converting enzyme (ACE) inhibitor, quinaprilat.Quinapril hydrochloride is chemically described as [3S-[2[R*(R*)], 3R*]]-2-[2...
Active IngredientQuinapril hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 40mg base; eq 5mg base; eq 20mg base; eq 10mg base
Market StatusPrescription
CompanyPfizer Pharms

2 of 6  
Drug NameAccuretic
PubMed HealthQuinapril/Hydrochlorothiazide (By mouth)
Drug ClassesACE Inhibitor/Thiazide Combination, Antihypertensive, Cardiovascular Agent
Active IngredientHydrochlorothiazide; quinapril hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; eq 20mg base; eq 10mg base; 12.5mg
Market StatusPrescription
CompanyPfizer Pharms

3 of 6  
Drug NameQuinapril hydrochloride
Drug LabelQuinapril hydrochloride is the hydrochloride salt of quinapril, the ethyl ester of a non-sulfhydryl, angiotensin-converting enzyme (ACE) inhibitor, quinaprilat.Quinapril hydrochloride is chemically described as [3S-[2[R*(R*)], 3R*]]-2-[2-[[1-(ethox...
Active IngredientQuinapril hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 5mg base; eq 20mg base; eq 40mg base; eq 10mg base
Market StatusPrescription
CompanyRanbaxy; Actavis Labs Fl; Teva; Aurobindo Pharma; Sun Pharm Inds; Lupin; Invagen Pharms; Mylan

4 of 6  
Drug NameAccupril
PubMed HealthQuinapril (By mouth)
Drug ClassesAntihypertensive, Cardiovascular Agent, Renal Protective Agent
Drug LabelACCUPRIL (quinapril hydrochloride) is the hydrochloride salt of quinapril, the ethyl ester of a non-sulfhydryl, angiotensin-converting enzyme (ACE) inhibitor, quinaprilat.Quinapril hydrochloride is chemically described as [3S-[2[R*(R*)], 3R*]]-2-[2...
Active IngredientQuinapril hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 40mg base; eq 5mg base; eq 20mg base; eq 10mg base
Market StatusPrescription
CompanyPfizer Pharms

5 of 6  
Drug NameAccuretic
PubMed HealthQuinapril/Hydrochlorothiazide (By mouth)
Drug ClassesACE Inhibitor/Thiazide Combination, Antihypertensive, Cardiovascular Agent
Active IngredientHydrochlorothiazide; quinapril hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; eq 20mg base; eq 10mg base; 12.5mg
Market StatusPrescription
CompanyPfizer Pharms

6 of 6  
Drug NameQuinapril hydrochloride
Drug LabelQuinapril hydrochloride is the hydrochloride salt of quinapril, the ethyl ester of a non-sulfhydryl, angiotensin-converting enzyme (ACE) inhibitor, quinaprilat.Quinapril hydrochloride is chemically described as [3S-[2[R*(R*)], 3R*]]-2-[2-[[1-(ethox...
Active IngredientQuinapril hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 5mg base; eq 20mg base; eq 40mg base; eq 10mg base
Market StatusPrescription
CompanyRanbaxy; Actavis Labs Fl; Teva; Aurobindo Pharma; Sun Pharm Inds; Lupin; Invagen Pharms; Mylan

4.2 Therapeutic Uses

... /Quinapril/ has proven to be very useful for the treatment of hypertension ... . /Salt not specified/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 893


The angiotensin converting enzyme (ACE) inhibitors appear to confer a special advantage in the treatment of patients with diabetes, slowing the development of diabetic glomerulopathy. They also have been shown to be effective in slowing the progression of other forms of chronic renal disease, such as glomerulosclerosis, & many of these patients also have hypertension. An ACE inhibitor is probably the preferred initial agent in the treatment of hypertensive patients with left ventricular hypertrophy. Patients with hypertension & ischemic heart disease are candidates for treatment with ACE inhibitors; this includes treatment in the immediate post-myocardial infarction period which has been shown to lead to improved ventricular function & reduced morbidity & mortality. /ACE inhibitors/ /Salt not specified/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 893


The combination of ... quinapril and hydrochlorothiazide is indicated in the treatment of hypertension. Fixed-dosage combinations generally are not recommended for initial therapy, but are utilized in maintenance therapy after the required dose is established in order to increase convenience, economy, and patient compliance. /Included in US product labeling/ /Salt not specified/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional. 22nd ed. Volume 1. MICROMEDEX Thomson Health Care, Greenwood Village, CO. 2002. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 215


Angiotensin converting enzyme (ACE) inhibitor /Salt not specified/

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 1441


For more Therapeutic Uses (Complete) data for QUINAPRIL HYDROCHLORIDE (6 total), please visit the HSDB record page.


4.3 Drug Warning

Reduce dose ... in patients with serum creatinine > or =221 umol/L (2.5 mg/dL). /ACE Inhibitors; from table/ /Salt not specified/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 553


May cause hyperkalemia in patients with renal impairment or in those receiving potassium-sparing agents. /ACE Inhibitors; from table/ /Salt not specified/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 553


Can cause acute renal failure in patients with severe bilateral renal artery stenosis or severe stenosis in artery to solitary kidney. /ACE Inhibitors; from table/ /Salt not specified/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 553


Conversion of quinapril to quinaprilat is reduced in patients with diminished liver function. /Salt not specified/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 824


For more Drug Warnings (Complete) data for QUINAPRIL HYDROCHLORIDE (12 total), please visit the HSDB record page.


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.)


Cardiovascular Agents

Agents that affect the rate or intensity of cardiac contraction, blood vessel diameter, or blood volume. (See all compounds classified as Cardiovascular Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Angiotensin-converting Enzyme Inhibitors [MoA]; Angiotensin Converting Enzyme Inhibitor [EPC]
5.3 Absorption, Distribution and Excretion

Absorption (bioavailability) of quinapril is 60%; time to peak serum concn is 2 hr; half-life (elimination) is 2 hr; protein binding is 97%; metabolism is in the liver. /from table/ /Salt not specified/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 557


Quinapril is rapidly absorbed (peak concns are achieved in 1 hr, but the peak may be delayed after food), & its rate but not extent of oral absorption (60%) may be reduced by food. Quinapril is metabolized to quinaprilat & to other minor metabolites, & quinaprilat is excreted in the urine (61%) & the feces (37%). Peak concns of quinaprilat in plasma are achieved in about 2 hr. Conversion of quinapril to quinaprilat is reduced in patients with diminished liver function. The initial half-life of quinaprilat is about 2 hr; a prolonged terminal half-life of about 25 hr may be due to high-affinity binding of the drug to tissue ACE. /Salt not specified/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 823


5.4 Metabolism/Metabolites

Cleavage of the ester moiety by hepatic esterases transforms quinapril hydrochloride, a prodrug, into quinaprilat, an ACE inhibitor that in vitro is about as potent as benazeprilat. ... Quinapril is metabolized to quinaprilat & to other minor metabolites ... .

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 823


5.5 Biological Half-Life

The initial half-life of /the metabolite/ quinaprilat is about 2 hr; a prolonged terminal half-life of about 25 hr may be due to high-affinity binding of the drug to tissue ACE. /Salt not specified/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 824


5.6 Mechanism of Action

Block formation of angiotensin II, promoting vasodilation & decreased aldosterone; also increased bradykinin & vasodilatory prostaglandins. /ACE Inhibitors; from table/ /Salt not specified/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 553


Quinapril is deesterified to the principal metabolite, quinaprilat, which is an inhibitor of ACE activity in human subjects and animals. ACE is a peptidyl dipeptidase that catalyzes the conversion of angiotensin I to the vasoconstrictor, angiotensin II. The effect of quinapril in hypertension and in congestive heart failure (CHF) appears to result primarily from the inhibition of circulating and tissue ACE activity, thereby reducing angiotensin II formation. Quinapril inhibits the elevation in blood pressure caused by iv administered angiotensin I, but has no effect on the pressor response to angiotensin II, norepinephrine or epinephrine. Angiotensin II also stimulates the secretion of aldosterone from the adrenal cortex, thereby facilitating renal sodium and fluid reabsorption. Reduced aldosterone secretion by quinapril may result in a small incr in serum potassium. In controlled hypertension trials, treatment with ACCUPRIL alone resulted in mean increases in potassium of 0.07 mmol/L ... . Removal of angiotensin II negative feedback on renin secretion leads to increased plasma renin activity (PRA). /Salt not specified/

Medical Economics Co; Physicians Desk Reference 56th ed p.2611 (2002)


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