Quinapril

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 category	D
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Protein binding	97%
Half-life	2 hours
Identifiers
CAS Registry Number	85441-61-8^Y
ATC code	C09AA06
PubChem	CID 54892
DrugBank	DB00881^Y
ChemSpider	49565^Y
UNII	RJ84Y44811^Y
KEGG	D03752^Y
ChEBI	CHEBI:8713^Y
ChEMBL	CHEMBL1592^Y
Chemical data
Formula	C₂₅H₃₀N₂O₅
Molecular 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
Physical data
Melting point	120 to 130 °C (248 to 266 °F)
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. 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")

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

Index of the circulatory system

Description	Anatomy Arteries head and neck arms chest abdomen legs Veins head and neck arms chest abdomen and pelvis legs Development Cells Physiology proteins

Disease	Congenital Neoplasms and cancer Lymphatic vessels Injury Vasculitis Other Symptoms and signs eponymous

Treatment	Procedures Drugs beta blockers channel blockers diuretics nonsympatholytic vasodilatory antihypertensives peripheral vasodilators renin–angiotensin system sympatholytic antihypertensives vasoprotectives