Quinapril

Quinapril, sold under the brand name Accupril^[2] by the Pfizer corporation, is a medication used to treat high blood pressure (hypertension), heart failure, and diabetic kidney disease.^[1][3] It is a first line treatment for high blood pressure.^[3] It is taken by mouth.^[1][3]

Quinapril

Clinical data
Trade names	Accupril, others
Other names	Quinapril hydrochloride (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a692026
License data	US DailyMed: Quinapril
Routes of administration	By mouth
ATC code	C09AA06 (WHO)
Legal status
Legal status	US: ℞-only[1] In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	97%
Elimination half-life	2 hours
Identifiers
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
CAS Number	85441-61-8 Y
PubChem CID	54892
IUPHAR/BPS	6350
DrugBank	DB00881 Y
ChemSpider	49565 Y
UNII	RJ84Y44811
KEGG	D03752 Y
ChEBI	CHEBI:8713 Y
ChEMBL	ChEMBL1592 Y
CompTox Dashboard (EPA)	DTXSID4023547
Chemical and physical data
Formula	C25H30N2O5
Molar mass	438.524 g·mol−1
3D model (JSmol)	Interactive image
Melting point	120 to 130 °C (248 to 266 °F)
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
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Common side effects include headaches, dizziness, feeling tired, and cough.^[3] Serious side effects may include liver problems, low blood pressure, angioedema, kidney problems, and high blood potassium.^[3] Use in pregnancy and breastfeeding is not recommended.^[4] It is among a class of drugs called ACE inhibitors and works by decreasing renin-angiotensin-aldosterone system activity.^[3]

Quinapril was patented in 1980 and came into medical use in 1989.^[5] It is available as a generic medication.^[6] In 2020, it was the 253rd most commonly prescribed medication in the United States, with more than 1 million prescriptions.^[7][8]

Medical uses

Quinapril is indicated for the treatment of high blood pressure (hypertension) and as adjunctive therapy in the management of heart failure.^[1] 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.^[1]

Contraindications

Contraindications include:^[9]

• 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^[9] include dizziness, cough, vomiting, upset stomach, angioedema, and fatigue.

Mechanism of action

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.

Nitrosamine controversy and voluntary recall

In April of 2022, Pfizer voluntarily recalled five batches of the drug because of the presence of a nitrosamine, N-Nitroso-quinapril. Testing found that the amount of nitrosamines was above the acceptable daily intake level (all humans are exposed to nitrosamines up to a certain daily level by cured and grilled meats, water, dairy products, and vegetables) set by the U.S.'s Food and Drug Administration (FDA). Though long-term ingestion of N-Nitroso-quinapril potentially might cause cancer in some individuals, there is not believed to be an imminent risk of harm.^[10][11]