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    Chemistry

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

    Quinapril

    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)

    API Reference Price

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    27-Jan-2021
    29-Jun-2024
    KGS
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    Average Price (USD/KGS)

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    DOSAGE - TABLET;ORAL - EQ 10MG BASE **Federal...DOSAGE - TABLET;ORAL - EQ 10MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 19885

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    DOSAGE - TABLET;ORAL - EQ 20MG BASE **Federal...DOSAGE - TABLET;ORAL - EQ 20MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 19885

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    DOSAGE - TABLET;ORAL - EQ 40MG BASE **Federal...DOSAGE - TABLET;ORAL - EQ 40MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 19885

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    DOSAGE - TABLET;ORAL - EQ 5MG BASE **Federal ...DOSAGE - TABLET;ORAL - EQ 5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 19885

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