Quinapril hydrochloride

Names

[ Name ]:
Quinapril hydrochloride

[Synonym ]:
(3S)-2-[(2S)-2-{[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisochinolin-3-carbonsäurehydrochlorid
(3S)-2-{N-[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]-L-alanyl}-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride (1:1)
(3S)-2-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride
Acuitel
3-Isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, (3S)-, hydrochloride (1:1)
ccupril
Acequin
quinapril HCl
2-<<1-ethoxycarbonyl)-3-phenylpropyl>amino>-1-oxopropyl>-1,2,3,4-tetrahydro-3-isoquinoline carboxylic acid monohydrochloride
Conan
ACCUPRIN
(3S)-2-{N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride
3-isoquinolinecarboxylic acid, 2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-, (3S)-, monohydrochloride
Quinapril hydrochloride
Acupril
(3S)-2-{N-[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]-L-alanyl}-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (1:1)
CI-906
Acuprel
MFCD00889215
ACCUPRO
Korec
acide (3S)-2-[(2S)-2-{[(1S)-1-(éthoxycarbonyl)-3-phénylpropyl]amino}propanoyl]-1,2,3,4-tétrahydroisoquinoléine-3-carboxylique chlorhydrate
Quinapril (hydrochloride)
QuinaprilHydrochloride

Biological Activity

[Description]:

Quinapril is a prodrug that belongs to the angiotensin-converting enzyme (ACE) inhibitor class of medications.Target: ACEQuinapril is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used in the treatment of hypertension and congestive heart failure. Quinapril is rapidly de-esterified after absorption to quinaprilat (the active diacid metabolite), a potent angiotensin converting enzyme (ACE) inhibitor. Quinapril is now firmly established as an effective and well tolerated ACE inhibitor for the treatment of patients with hypertension and congestive heart failure. Quinapril 40 mg/day also significantly reduced the incidence of ischaemic events in patients undergoing CABG in one study [1, 2]. An overview of 32 clinical trials of ACE inhibitors in heart failure showed that no significant heterogeneity in mortality was found among enalapril, ramipril, quinapril, captopril, lisinopril, benazepril, perindopril and cilazapril. Initiation of therapy with captopril, ramipril, and trandolapril at least 3 days after an acute MI resulted in all-cause mortality risk reductions of 18 to 27% [3].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Angiotensin-converting Enzyme (ACE)

Research Areas >> Cardiovascular Disease

[References]

[1]. Song, J.C. and C.M. White, Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet, 2002. 41(3): p. 207-24.

[2]. Culy, C.R. and B. Jarvis, Quinapril: a further update of its pharmacology and therapeutic use in cardiovascular disorders. Drugs, 2002. 62(2): p. 339-85.

[3]. Klutchko, S., et al., Synthesis of novel angiotensin converting enzyme inhibitor quinapril and related compounds. A divergence of structure-activity relationships for non-sulfhydryl and sulfhydryl types. J Med Chem, 1986. 29(10): p. 1953-61.

[Related Small Molecules]

Chemical & Physical Properties

[ Boiling Point ]:
662ºC at 760 mmHg

[ Melting Point ]:
120-130ºC

[ Molecular Formula ]:
C₂₅H₃₁ClN₂O₅

[ Molecular Weight ]:
474.977

[ Flash Point ]:
354.1ºC

[ Exact Mass ]:
474.192139

[ PSA ]:
95.94000

[ LogP ]:
3.69790

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NW7176000

CHEMICAL NAME :: 3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-2-(2-((1-(ethoxycarbonyl)-3-phenyl propyl) amino)-1-oxopropyl)-, monohydrochloride, (3S-(2(R*(R*)),3R*))-

CAS REGISTRY NUMBER :: 82586-55-8

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C25-H30-N2-O5.Cl-H

MOLECULAR WEIGHT :: 475.03

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3541 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ANGIAB Angiology. (Angiology Research Found., Inc., 320 Northern Blvd., Great Neck, NY 11021) V.1- 1950- Volume(issue)/page/year: 40,335,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 107 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ANGIAB Angiology. (Angiology Research Found., Inc., 320 Northern Blvd., Great Neck, NY 11021) V.1- 1950- Volume(issue)/page/year: 40,335,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1739 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ANGIAB Angiology. (Angiology Research Found., Inc., 320 Northern Blvd., Great Neck, NY 11021) V.1- 1950- Volume(issue)/page/year: 40,335,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 504 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ANGIAB Angiology. (Angiology Research Found., Inc., 320 Northern Blvd., Great Neck, NY 11021) V.1- 1950- Volume(issue)/page/year: 40,335,1989

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,740,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3640 mg/kg/52W-I

TOXIC EFFECTS :: Blood - other changes Nutritional and Gross Metabolic - changes in sodium Related to Chronic Data - death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 46,121,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 3650 mg/kg/1Y-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 46,139,1993 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 700 mg/kg

SEX/DURATION :: female 15-21 day(s) after conception lactating female 1-21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 17,684,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 330 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 46,197,1993

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 78 mg/kg

SEX/DURATION :: female 17-21 day(s) after conception lactating female 1-21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 49,465,1995

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
NW7176000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Determination of losartan potassium, quinapril hydrochloride and hydrochlorothiazide in pharmaceutical preparations using derivative spectrophotometry and chromatographic-densitometric method.

Acta Pol. Pharm. 70(6) , 967-76, (2013)

Two methods, spectrophotometric and chromatographic-densitometric ones, were developed for determination of losartan potassium, quinapril hydrochloride and hydrochlorothiazide in pharmaceutical prepar...

Hepatic, intestinal, renal, and plasma hydrolysis of prodrugs in human, cynomolgus monkey, dog, and rat: implications for in vitro-in vivo extrapolation of clearance of prodrugs.

Drug Metab. Dispos. 42(9) , 1522-31, (2014)

Hydrolysis plays an important role in metabolic activation of prodrugs. In the current study, species and in vitro system differences in hepatic and extrahepatic hydrolysis were investigated for 11 pr...

The impact of lipoic acid on endothelial function and proteinuria in quinapril-treated diabetic patients with stage I hypertension: results from the QUALITY study.

J. Cardiovasc. Pharmacol. Ther. 17(2) , 139-45, (2012)

We sought to determine whether a combination of angiotensin-converting enzyme inhibitors (ACEIs) and the nutraceutical α-lipoic acid (ALA) regulates blood pressure, endothelial function, and proteinur...

Related Compounds

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