| Revision as of 12:19, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{drugbox}} taken from revid 456815872 of page Quinapril for the Chem/Drugbox validation project (updated: 'DrugBank'). |
Latest revision as of 23:31, 20 October 2024 edit Surnamesurname (talk | contribs)3 editsmNo edit summary |
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{{Short description|ACE inhibitor used in the treatment of hypertension and congestive heart failure}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Use dmy dates|date=March 2022}} |
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{{Drugbox |
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{{Infobox drug |
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| Watchedfields = changed |
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| verifiedrevid = 411999350 |
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| verifiedrevid = 464378463 |
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| IUPAC_name = (3''S'')-2-amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid |
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| type = <!-- empty --> |
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| image = Quinapril.svg |
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| image = Quinapril structure.svg |
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| width = 180 |
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| width = 222 |
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| alt = |
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| caption = |
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| USAN = Quinapril hydrochloride |
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<!--Clinical data--> |
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<!-- Clinical data --> |
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| pronounce = |
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| tradename = Accupril |
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| tradename = Accupril, others |
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| Drugs.com = {{drugs.com|monograph|quinapril-hydrochloride}} |
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| Drugs.com = {{drugs.com|monograph|quinapril-hydrochloride}} |
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| MedlinePlus = a692026 |
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| MedlinePlus = a692026 |
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| DailyMedID = Quinapril |
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| pregnancy_category = D |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU_comment = |
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| pregnancy_category= |
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| routes_of_administration = ] |
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| class = |
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| ATCvet = |
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| ATC_prefix = C09 |
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| ATC_suffix = AA06 |
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| ATC_supplemental = |
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<!-- Legal status --> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
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| legal_AU_comment = |
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| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
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| legal_BR_comment = |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> |
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| legal_UK_comment = |
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| legal_US = Rx-only |
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| legal_US_comment = <ref name="Accupril FDA label">{{cite web | title=Accupril- quinapril hydrochloride tablet, film coated Accupril- quinapril tablet, film coated | website=DailyMed | date=26 August 2021 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=63cf5651-d52c-4d27-9fd4-ed9cd9724dff | access-date=25 March 2022}}</ref> |
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| legal_EU = |
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| legal_EU_comment = |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = Rx-only |
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| legal_status = Rx-only |
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| routes_of_administration = Oral |
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<!--Pharmacokinetic data--> |
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<!-- Pharmacokinetic data --> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = 97% |
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| protein_bound = 97% |
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| metabolism = |
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| metabolism = |
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| metabolites = |
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| onset = |
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| elimination_half-life = 2 hours |
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| elimination_half-life = 2 hours |
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| duration_of_action = |
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| excretion = |
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<!--Identifiers--> |
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<!-- Identifiers --> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 85441-61-8 |
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| CAS_number = 85441-61-8 |
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| CAS_supplemental = |
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| ATC_prefix = C09 |
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| ATC_suffix = AA06 |
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| PubChem = 54892 |
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| PubChem = 54892 |
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| IUPHAR_ligand = 6350 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00881 |
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| DrugBank = DB00881 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D03752 |
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| KEGG = D03752 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 8713 |
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| ChEBI = 8713 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1592 |
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| ChEMBL = 1592 |
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| NIAID_ChemDB = |
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| PDB_ligand = |
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| synonyms = |
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<!--Chemical data--> |
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<!-- Chemical and physical data --> |
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| IUPAC_name = (3''S'')-2-amino]propanoyl]-3,4-dihydro-1''H''-isoquinoline-3-carboxylic acid |
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| C=25 | H=30 | N=2 | O=5 |
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| C=25 | H=30 | N=2 | O=5 |
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| molecular_weight = 438.516 g/mol |
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| smiles = O=C(OCC)(N(C(=O)N2(C(=O)O)Cc1c(cccc1)C2)C)CCc3ccccc3 |
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| SMILES = O=C(OCC)(N(C(=O)N2(C(=O)O)Cc1c(cccc1)C2)C)CCc3ccccc3 |
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| InChI = 1/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 |
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| InChIKey = JSDRRTOADPPCHY-HSQYWUDLBG |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChI_comment = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JSDRRTOADPPCHY-HSQYWUDLSA-N |
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| StdInChIKey = JSDRRTOADPPCHY-HSQYWUDLSA-N |
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| density = |
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| density_notes = |
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| melting_point = 120 |
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| melting_high = 130 |
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| melting_notes = |
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| boiling_point = |
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| boiling_notes = |
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| solubility = |
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| sol_units = |
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| specific_rotation = |
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}} |
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}} |
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<!-- Definition and medical uses --> |
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'''Quinapril''', sold under the brand name '''Accupril'''<ref>{{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}}</ref> by the ] corporation, is a ] used to treat ] (hypertension), ], and ].<ref name="Accupril FDA label" /><ref name=AHFS2019/> It is a first line treatment for high blood pressure.<ref name=AHFS2019/> It is taken ].<ref name="Accupril FDA label" /><ref name=AHFS2019/> |
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<!-- Side effects and mechanisms --> |
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Common side effects include headaches, dizziness, feeling tired, and cough.<ref name=AHFS2019/> Serious side effects may include liver problems, ], ], ], and ].<ref name=AHFS2019/> Use in ] and ] is not recommended.<ref name=Preg2019>{{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}}</ref> It is among a class of drugs called ] and works by decreasing ] activity.<ref name=AHFS2019>{{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}}</ref> |
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<!-- Society and culture --> |
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Quinapril was patented in 1980 and came into medical use in 1989.<ref name=Fis2006>{{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}}</ref> It is available as a ].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=172|edition=76}}</ref> In 2020, it was the 253rd most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title = The Top 300 of 2020 | url = https://clincalc.com/DrugStats/Top300Drugs.aspx | website = ClinCalc | access-date = 7 October 2022}}</ref><ref>{{cite web | title = Quinapril - Drug Usage Statistics | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Quinapril | access-date = 7 October 2022}}</ref> |
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==Medical uses== |
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Quinapril is ] for the treatment of high blood pressure (]) and as adjunctive therapy in the management of ].<ref name="Accupril FDA label" /> It may be used for the treatment of hypertension by itself or in combination with ]s, and with diuretics and ] for heart failure.<ref name="Accupril FDA label" /> |
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==Contraindications== |
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Contraindications include:<ref name="cleveland" /> |
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* Pregnancy |
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* Impaired renal and liver function |
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* Patients with a history of angioedema related to previous treatment with an ACE inhibitor |
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* Hypersensitivity to Quinapril |
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==Side effects== |
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]s of Quinapril<ref name="cleveland">{{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}}</ref> include dizziness, cough, vomiting, upset stomach, ], and ]. |
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==Mechanism of action== |
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Quinapril inhibits ], an enzyme which ] the formation of ] ] from its precursor, ]. ] is a powerful ] and increases blood pressure through a variety of mechanisms. Due to reduced angiotensin production, plasma concentrations of ] are also reduced, resulting in increased excretion of ] in the urine and increased concentrations of ] in the blood. |
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==Partial Recall== |
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In April of 2022, ] voluntarily recalled five batches of the drug because of the presence of a ], NNitroso-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 ] (FDA). Though long-term ingestion of NNitroso-quinapril potentially might cause cancer in some individuals, there is not believed to be an imminent risk of harm.<ref>{{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=] }}</ref><ref>{{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=] | date=22 April 2022 }}</ref> |
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==References== |
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{{reflist}} |
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==External links== |
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* {{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 }} |
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{{ACE inhibitors}} |
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{{Angiotensin receptor modulators}} |
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{{Portal bar | Medicine}} |
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