Quinaprilat free base| CAS# 82768-85-2 | ACE inhibitor

MedKoo Cat#: 564690 | Name: Quinaprilat free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Quinaprilat is the active metabolite of quinapril, an angiotensin-converting enzyme inhibitor (ACE inhibitor) used in the treatment of hypertension and congestive heart failure. Quinaprilat reduces myocardial infarct size involving nitric oxide production and mitochondrial KATP channel in rabbits. Quinaprilat during cardioplegic arrest in the rabbit to prevent ischemia-reperfusion injury. quinaprilat attenuates the LPC-induced increase in [Ca2+]i, and that the protective effect of quinaprilat on the LPC-induced change may not be related to a decrease in angiotensin II production or an increase in bradykinin production.

Chemical Structure

Quinaprilat free base

CAS#82768-85-2 (free base)

Theoretical Analysis

MedKoo Cat#: 564690

Name: Quinaprilat free base

CAS#: 82768-85-2 (free base)

Chemical Formula: C23H26N2O5

Exact Mass: 410.1842

Molecular Weight: 410.47

Elemental Analysis: C, 67.30; H, 6.38; N, 6.82; O, 19.49

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 425.00	2 Weeks
10mg	USD 650.00	2 Weeks

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Related CAS #

82586-58-1 (HCl) 82768-85-2 (free base) 1435786-09-6 (hydrate)

Synonym

CI928; CI 928; CI-928; Quinaprilat

IUPAC/Chemical Name

(3S)-2-[(2S)-2-[[(1S)-1-Carboxy-3-phenylpropyl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid

InChi Key

FLSLEGPOVLMJMN-YSSFQJQWSA-N

InChi Code

InChI=1S/C23H26N2O5/c1-15(24-19(22(27)28)12-11-16-7-3-2-4-8-16)21(26)25-14-18-10-6-5-9-17(18)13-20(25)23(29)30/h2-10,15,19-20,24H,11-14H2,1H3,(H,27,28)(H,29,30)/t15-,19-,20-/m0/s1

SMILES Code

O=C([C@H]1N(C([C@@H](N[C@H](C(O)=O)CCC2=CC=CC=C2)C)=O)CC3=C(C=CC=C3)C1)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO and Methanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO and Methanol

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#C23M06C27

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Quinaprilat is a dicarboxylic acid resulting from the hydrolysis of the ethyl ester group of quinapril to give the corresponding dicarboxylic acid. The active angiotensin-converting enzyme inhibitor (ACE inhibitor) of the prodrug quinapril. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a vasodilator agent. It is a dicarboxylic acid, a member of isoquinolines and a tertiary carboxamide.

In vitro activity:

This study examined the effects of propofol (50 μM), quinaprilat and enalaprilat (10-5 M) on fibrinolysis, oxidative stress parameters, and nitric oxide bioavailability in human umbilical vein endothelial cells (HUVECs). These findings suggest that the studied angiotensin-converting enzyme inhibitors exerted protective effects against endothelial cell dysfunction caused by propofol, independently of hemodynamics. Reference: J Renin Angiotensin Aldosterone Syst. 2017 Jan;18(1):1470320316687197. https://pubmed.ncbi.nlm.nih.gov/28090801/

In vivo activity:

Angiotensin converting enzyme (ACE) inhibitors, including quinapril, improve survival and quality of life in human patients and small animals with cardiovascular and renal disease. There is limited information regarding their effects in healthy, mature horses. Quinaprilat was detected in all horses following oral administration of quinapril; however, it was below the limit of quantification of the assay for most horses in the 120 mg dosing group. These results suggest that quinapril has sufficient oral absorption to produce inhibition of ACE in healthy horses. provides a potential treatment for horses with cardiovascular and renal disease. Reference: Equine Vet J. 2014 Nov;46(6):729-33. https://pubmed.ncbi.nlm.nih.gov/24175935/

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00
	Methanol	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 410.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wojewodzka-Zelezniakowicz M, Gromotowicz-Poplawska A, Kisiel W, Konarzewska E, Szemraj J, Ladny JR, Chabielska E. Angiotensin-converting enzyme inhibitors attenuate propofol-induced pro-oxidative and antifibrinolytic effect in human endothelial cells. J Renin Angiotensin Aldosterone Syst. 2017 Jan;18(1):1470320316687197. doi: 10.1177/1470320316687197. PMID: 28090801; PMCID: PMC5843862. 2. Knütter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M. Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. PMID: 18713951. 3. Davis JL, Kruger K, LaFevers DH, Barlow BM, Schirmer JM, Breuhaus BA. Effects of quinapril on angiotensin converting enzyme and plasma renin activity as well as pharmacokinetic parameters of quinapril and its active metabolite, quinaprilat, after intravenous and oral administration to mature horses. Equine Vet J. 2014 Nov;46(6):729-33. doi: 10.1111/evj.12206. Epub 2014 Jan 7. PMID: 24175935. 4. van Beusekom HM, Ferrero V, Ribichini F, van der Giessen WJ. Quinaprilat-eluting stents do not attenuate intimal thickening following stenting in porcine coronary arteries. Atherosclerosis. 2009 Jul;205(1):120-5. doi: 10.1016/j.atherosclerosis.2008.11.029. Epub 2008 Dec 6. PMID: 19135197.

In vitro protocol:

In vivo protocol:

1. Davis JL, Kruger K, LaFevers DH, Barlow BM, Schirmer JM, Breuhaus BA. Effects of quinapril on angiotensin converting enzyme and plasma renin activity as well as pharmacokinetic parameters of quinapril and its active metabolite, quinaprilat, after intravenous and oral administration to mature horses. Equine Vet J. 2014 Nov;46(6):729-33. doi: 10.1111/evj.12206. Epub 2014 Jan 7. PMID: 24175935. 2. van Beusekom HM, Ferrero V, Ribichini F, van der Giessen WJ. Quinaprilat-eluting stents do not attenuate intimal thickening following stenting in porcine coronary arteries. Atherosclerosis. 2009 Jul;205(1):120-5. doi: 10.1016/j.atherosclerosis.2008.11.029. Epub 2008 Dec 6. PMID: 19135197.

1: Ozkizilcik A, Sysavanh F, Patel S, Tandon I, Balachandran K. Local Renin- Angiotensin System Signaling Mediates Cellular Function of Aortic Valves. Ann Biomed Eng. 2021 Dec;49(12):3550-3562. doi: 10.1007/s10439-021-02876-y. Epub 2021 Oct 26. PMID: 34704164. 2: Sun S, Wei Y, Wang H, Cao Y, Deng B. A novel electrochemiluminescence sensor coupled with capillary electrophoresis for simultaneous determination of quinapril hydrochloride and its metabolite quinaprilat hydrochloride in human plasma. Talanta. 2018 Mar 1;179:213-220. doi: 10.1016/j.talanta.2017.10.050. Epub 2017 Nov 4. PMID: 29310224. 3: Wojewodzka-Zelezniakowicz M, Gromotowicz-Poplawska A, Kisiel W, Konarzewska E, Szemraj J, Ladny JR, Chabielska E. Angiotensin-converting enzyme inhibitors attenuate propofol-induced pro-oxidative and antifibrinolytic effect in human endothelial cells. J Renin Angiotensin Aldosterone Syst. 2017 Jan;18(1):1470320316687197. doi: 10.1177/1470320316687197. PMID: 28090801; PMCID: PMC5843862. 4: de Diego M, Godoy R, Mennickent S, Vergara C, Charnock H, Hernández C. Comparison of Stability-Indicating LC Methods Using Light Scattering and Photodiode Array Detection with Monolithic Column for Determination of Quinapril and Hydrochlorothiazide. J Chromatogr Sci. 2016 Sep;54(8):1346-51. doi: 10.1093/chromsci/bmw068. Epub 2016 May 10. PMID: 27165572. 5: Tarkiainen EK, Tornio A, Holmberg MT, Launiainen T, Neuvonen PJ, Backman JT, Niemi M. Effect of carboxylesterase 1 c.428G > A single nucleotide variation on the pharmacokinetics of quinapril and enalapril. Br J Clin Pharmacol. 2015 Nov;80(5):1131-8. doi: 10.1111/bcp.12667. Epub 2015 Jun 11. PMID: 25919042; PMCID: PMC4631185. 6: Davis JL, Kruger K, LaFevers DH, Barlow BM, Schirmer JM, Breuhaus BA. Effects of quinapril on angiotensin converting enzyme and plasma renin activity as well as pharmacokinetic parameters of quinapril and its active metabolite, quinaprilat, after intravenous and oral administration to mature horses. Equine Vet J. 2014 Nov;46(6):729-33. doi: 10.1111/evj.12206. Epub 2014 Jan 7. PMID: 24175935. 7: Fateev MM, Sidorov AV, Grigor'eva MV, Rakov AA, Fateeva KM. Heart rate variability in conscious and anesthetized rats under the action of angiotensin converting enzyme inhibitors. Bull Exp Biol Med. 2012 Mar;152(5):590-4. English, Russian. doi: 10.1007/s10517-012-1583-1. PMID: 22803141. 8: Chen L, Kim SM, Eisner C, Oppermann M, Huang Y, Mizel D, Li L, Chen M, Sequeira Lopez ML, Weinstein LS, Gomez RA, Schnermann J, Briggs JP. Stimulation of renin secretion by angiotensin II blockade is Gsalpha-dependent. J Am Soc Nephrol. 2010 Jun;21(6):986-92. doi: 10.1681/ASN.2009030307. Epub 2010 Apr 15. PMID: 20395378; PMCID: PMC2900955. 9: Kieback AG, Felix SB, Reffelmann T. Quinaprilat: a review of its pharmacokinetics, pharmacodynamics, toxicological data and clinical application. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1337-47. doi: 10.1517/17425250903282773. PMID: 19761414. 10: Yuan H, Feng B, Yu Y, Chupka J, Zheng JY, Heath TG, Bond BR. Renal organic anion transporter-mediated drug-drug interaction between gemcabene and quinapril. J Pharmacol Exp Ther. 2009 Jul;330(1):191-7. doi: 10.1124/jpet.108.149476. Epub 2009 Apr 6. PMID: 19349522. 11: Sora I, Cristea E, Albu F, Udrescu S, David V, Medvedovici A. LC-MS/MS assay of quinapril and its metabolite quinaprilat for drug bioequivalence evaluation: prospective, concurrential and retrospective method validation. Bioanalysis. 2009 Apr;1(1):71-86. doi: 10.4155/bio.09.5. PMID: 21083190. 12: Lausević-Vuk L. [Hemodynamic effects of intravenous administration of ACE inhibitor in prevention of heart failure following coronary artery bypass surgery]. Med Pregl. 2008 Sep-Oct;61(9-10):512-6. Serbian. doi: 10.2298/mpns0810512l. PMID: 19203070. 13: van Beusekom HM, Ferrero V, Ribichini F, van der Giessen WJ. Quinaprilat- eluting stents do not attenuate intimal thickening following stenting in porcine coronary arteries. Atherosclerosis. 2009 Jul;205(1):120-5. doi: 10.1016/j.atherosclerosis.2008.11.029. Epub 2008 Dec 6. PMID: 19135197. 14: Dasandi B, Shah S; Shivprakash. Determination of quinapril and quinaprilat in human plasma by ultraperformance liquid chromatography-electrospray ionization mass spectrometry. Biomed Chromatogr. 2009 May;23(5):492-8. doi: 10.1002/bmc.1143. PMID: 19016233. 15: Delli Gatti C, Osto E, Kouroedov A, Eto M, Shaw S, Volpe M, Lüscher TF, Cosentino F. Pulsatile stretch induces release of angiotensin II and oxidative stress in human endothelial cells: effects of ACE inhibition and AT1 receptor antagonism. Clin Exp Hypertens. 2008 Oct;30(7):616-27. doi: 10.1080/10641960802443183. PMID: 18855265. 16: Parekh SA, Pudage A, Joshi SS, Vaidya VV, Gomes NA, Kamat SS. Simultaneous determination of hydrochlorothiazide, quinapril and quinaprilat in human plasma by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2008 Sep 15;873(1):59-69. doi: 10.1016/j.jchromb.2008.07.046. Epub 2008 Aug 7. PMID: 18723407. 17: Knütter I, Wollesky C, Kottra G, Hahn MG, Fischer W, Zebisch K, Neubert RH, Daniel H, Brandsch M. Transport of angiotensin-converting enzyme inhibitors by H+/peptide transporters revisited. J Pharmacol Exp Ther. 2008 Nov;327(2):432-41. doi: 10.1124/jpet.108.143339. Epub 2008 Aug 19. PMID: 18713951. 18: Rojanasthien N, Nasangiam N, Kumsorn B, Roongapinun S, Jengjareon A. Pharmacokinetics and bioequivalence study of the two 20-mg quinapril hydrochloride tablet formulations in healthy Thai male volunteers. J Med Assoc Thai. 2008 May;91(5):739-46. PMID: 18672641. 19: van Esch JH, van Gool JM, de Bruin RJ, Payne JR, Montgomery HE, Hectors M, Deinum J, Dive V, Jan Danser AH. Different contributions of the angiotensin- converting enzyme C-domain and N-domain in subjects with the angiotensin- converting enzyme II and DD genotype. J Hypertens. 2008 Apr;26(4):706-13. doi: 10.1097/HJH.0b013e3282f465d2. PMID: 18327080. 20: Infanger M, Faramarzi S, Grosse J, Kurth E, Ulbrich C, Bauer J, Wehland M, Kreutz R, Kossmehl P, Paul M, Grimm D. Expression of vascular endothelial growth factor and receptor tyrosine kinases in cardiac ischemia/reperfusion injury. Cardiovasc Pathol. 2007 Sep-Oct;16(5):291-9. doi: 10.1016/j.carpath.2007.04.001. Epub 2007 Jun 20. PMID: 17868880.