Quinapril

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Quinapril

Systematic (IUPAC) name
(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Clinical data
Trade names	Accupril
AHFS/Drugs.com	monograph
MedlinePlus	a692026
Pregnancy cat.	D
Legal status	℞ Prescription only
Routes	Oral
Pharmacokinetic data
Protein binding	97%
Half-life	2 hours
Identifiers
CAS number	85441-61-8^Y
ATC code	C09AA06
PubChem	CID 54892
DrugBank	DB00881
ChemSpider	49565^Y
UNII	RJ84Y44811^Y
KEGG	D03752^Y
ChEBI	CHEBI:8713^Y
ChEMBL	CHEMBL1592^Y
Chemical data
Formula	C₂₅H₃₀N₂O₅
Mol. mass	438.516 g/mol
SMILES O=C(OCC)[C@@H](N[C@H](C(=O)N2[C@H](C(=O)O)Cc1c(cccc1)C2)C)CCc3ccccc3
InChI InChI=1S/C25H30N2O5/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)/t17-,21-,22-/m0/s1^Y Key:JSDRRTOADPPCHY-HSQYWUDLSA-N^Y
Y (what is this?) (verify)

Quinapril (marketed under the brand name Accupril by Pfizer) is an angiotensin-converting enzyme inhibitor (ACE inhibitor) used in the treatment of hypertension and congestive heart failure.

Pharmacology

Quinapril is a prodrug. It is converted to its active metabolite, quinaprilat, in the liver.

Mechanism of action

Main article: ACE inhibitor

See also: Angiotensin and renin-angiotensin system

Quinapril inhibits angiotensin converting enzyme, an enzyme which catalyses the formation of angiotensin II from its precursor, angiotensin I. Angiotensin II is a powerful vasoconstrictor and increases blood pressure through a variety of mechanisms. Due to reduced angiotensin production, plasma concentrations of aldosterone are also reduced, resulting in increased excretion of sodium in the urine and increased concentrations of potassium in the blood.

Indications

Quinapril is indicated for the treatment of high blood pressure (hypertension) and as adjunctive therapy in the management of heart failure. It may be used for the treatment of hypertension by itself or in combination with thiazide diuretics, and with diuretics and digoxin for heart failure.

Contraindications

Pregnancy
Impaired renal and liver function
Patients with a history of angioedema related to previous treatment with an ACE inhibitor.
Hypersensitivity to quinapril

Side effects

Side effects of quinapril include dizziness, cough, vomiting, upset stomach, angioedema and fatigue.

External links

Antihypertensives: agents acting on the renin–angiotensin system (C09)

ACE inhibitors
("-pril")

Sulfhydryl-containing: Captopril
Zofenopril

Dicarboxylate-containing: Enalapril^#
Ramipril
Quinapril (+HCT)
Perindopril
Lisinopril (+HCT)
Benazepril

Phosphonate-containing: Fosinopril (+HCT)

AIIRAs/
("-sartan")

Renin inhibitors/
("-kiren")

Aliskiren (+amlodipine, +amlodipine and HCT)
Remikiren^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: VAS

anat (a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot

noco/syva/cong/lyvd/tumr, sysi/epon, injr

proc, drug (C2s+n/3/4/5/7/8/9)

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