quinapril
{{Short description|ACE inhibitor used in the treatment of hypertension and congestive heart failure}}
{{Use dmy dates|date=March 2022}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 464378463
| type =
| image = Quinapril structure.svg
| width = 222
| alt =
| caption =
| USAN = Quinapril hydrochloride
| pronounce =
| tradename = Accupril, others
| Drugs.com = {{drugs.com|monograph|quinapril-hydrochloride}}
| MedlinePlus = a692026
| DailyMedID = Quinapril
| pregnancy_AU =
| pregnancy_AU_comment =
| pregnancy_category=
| routes_of_administration = By mouth
| class =
| ATCvet =
| ATC_prefix = C09
| ATC_suffix = AA06
| ATC_supplemental =
| legal_AU =
| legal_AU_comment =
| legal_BR =
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| legal_CA_comment =
| legal_DE =
| legal_DE_comment =
| legal_NZ =
| legal_NZ_comment =
| legal_UK =
| legal_UK_comment =
| legal_US = Rx-only
| legal_EU =
| legal_EU_comment =
| legal_UN =
| legal_UN_comment =
| legal_status = Rx-only
| bioavailability =
| protein_bound = 97%
| metabolism =
| metabolites =
| onset =
| elimination_half-life = 2 hours
| duration_of_action =
| excretion =
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 85441-61-8
| CAS_supplemental =
| PubChem = 54892
| IUPHAR_ligand = 6350
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00881
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 49565
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = RJ84Y44811
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D03752
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8713
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1592
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =
| IUPAC_name = (3S)-2-[(2S)-2-
| C=25 | H=30 | N=2 | O=5
| SMILES = O=C(OCC)[C@@H](N[C@H](C(=O)N2[C@H](C(=O)O)Cc1c(cccc1)C2)C)CCc3ccccc3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JSDRRTOADPPCHY-HSQYWUDLSA-N
| density =
| density_notes =
| melting_point = 120
| melting_high = 130
| melting_notes =
| boiling_point =
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}}
Quinapril, sold under the brand name Accupril{{Cite web |title=ACCUPRIL® Indications and Usage (quinapril HCl) {{!}} Pfizer Medical Information - US |url=https://www.pfizermedicalinformation.com/en-us/accupril/indications-usage |access-date=2023-10-25 |website=www.pfizermedicalinformation.com}} by the Pfizer corporation, is a medication used to treat high blood pressure (hypertension), heart failure, and diabetic kidney disease. It is a first line treatment for high blood pressure. It is taken by mouth.
Common side effects include headaches, dizziness, feeling tired, and cough. Serious side effects may include liver problems, low blood pressure, angioedema, kidney problems, and high blood potassium. Use in pregnancy and breastfeeding is not recommended.{{cite web |title=Quinapril Pregnancy and Breastfeeding Warnings |url=https://www.drugs.com/pregnancy/quinapril.html |website=Drugs.com |access-date=3 March 2019 |language=en}} It is among a class of drugs called ACE inhibitors and works by decreasing renin-angiotensin-aldosterone system activity.{{cite web |title=Quinapril Hydrochloride Monograph for Professionals |url=https://www.drugs.com/monograph/quinapril-hydrochloride.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 |language=en}}
Quinapril was patented in 1980 and came into medical use in 1989.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=468 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA468 |language=en}} It is available as a generic medication.{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=172|edition=76}} In 2020, it was the 253rd most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}{{cite web | title = Quinapril - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Quinapril | access-date = 7 October 2022}}
Medical uses
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
Side effects
Side effects of Quinapril{{Cite web |title=Angiotensin-Converting Enzyme (ACE) Inhibitors |url=https://my.clevelandclinic.org/health/treatments/21934-ace-inhibitors |access-date=2023-10-25 |website=Cleveland Clinic |language=en}} 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.{{Cite web | url=https://www.msn.com/en-us/health/medical/pfizer-recalls-blood-pressure-tablets-due-to-increased-cancer-risk/ar-AAWAJEb?ocid=msedgntp&cvid=8bfaabe687e342029036240b1b7400c1 | title=Pfizer recalls blood pressure tablets due to increased cancer risk | website=MSN }}{{Cite web | url=https://www.fda.gov/safety/recalls-market-withdrawals-safety-alerts/pfizer-voluntary-nationwide-recall-lots-accuprilr-quinapril-hcl-due-n-nitroso-quinapril-content | title=Pfizer Voluntary Nationwide Recall of Lots of ACCUPRIL® (Quinapril HCL) Due to N-Nitroso-Quinapril Content | website=Food and Drug Administration | date=22 April 2022 }}
References
{{reflist}}
External links
- {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/quinapril%20hydrochloride | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Quinapril hydrochloride }}
{{ACE inhibitors}}
{{Angiotensin receptor modulators}}
{{Portal bar | Medicine}}
Category:Drugs developed by Pfizer
Category:Tetrahydroisoquinolines