Quinaprilat HCl | CAS#82586-58-1 | ACE Inhibitor

MedKoo Cat#: 526074 | Name: Quinaprilat HCl

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 HCl

CAS#82586-58-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 526074

Name: Quinaprilat HCl

CAS#: 82586-58-1 (HCl)

Chemical Formula: C23H27ClN2O5

Exact Mass: 0.0000

Molecular Weight: 446.93

Elemental Analysis: C, 61.81; H, 6.09; Cl, 7.93; N, 6.27; O, 17.90

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Related CAS #

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

Synonym

Quinaprilat; CI 928; CI-928; CI928;

IUPAC/Chemical Name

(S)-2-(((S)-1-carboxy-3-phenylpropyl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

InChi Key

YQJDLRLEBDSBCP-ZAFWUOJLSA-N

InChi Code

InChI=1S/C23H26N2O5.ClH/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);1H/t15-,19-,20-;/m0./s1

SMILES Code

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

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

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Instruction

View handling instruction

Biological target:

Quinaprilat hydrate mediates the interaction of organic anion transporter 3 (hOAT3) which can promote renal active secretion of quinapril that increases uptake of quinaprilat to 25-fold in HEK293 cells. Quinaprilat hydrate can inhibit the activity of protein kinase C (PKC) by activing the B1 receptor resulting in the release of NO in human lung microvascular endothelial (HLMVE) cells.

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

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 446.93 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: 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. 2: 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. 3: 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. 4: 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. 5: 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. 6: 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. 7: 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. 8: Kieback AG, Grohmann A, Baumann G, Felix SB. Haemodynamic effects of intravenous quinaprilat in comparison to sodium nitroprusside in patients with chronic heart failure. Int J Cardiol. 2007 Sep 14;121(1):102-4. doi: 10.1016/j.ijcard.2006.08.040. Epub 2006 Nov 13. PMID: 17098309. 9: Steinhauff S, Pehlivanli S, Bakovic-Alt R, Meiser BM, Becker BF, von Scheidt W, Weis M. Beneficial effects of quinaprilat on coronary vasomotor function, endothelial oxidative stress, and endothelin activation after human heart transplantation. Transplantation. 2004 Jun 27;77(12):1859-65. doi: 10.1097/01.tp.0000131148.78203.b7. PMID: 15223904. 10: Kwapisz MM, Müller M, Schindler E, Demir S, Veit M, Roth P, Hempelmann G. The effect of intravenous quinaprilat on plasma cytokines and hemodynamic variables during cardiac surgery. J Cardiothorac Vasc Anesth. 2004 Feb;18(1):53-8. doi: 10.1053/j.jvca.2003.10.011. PMID: 14973800. 11: Appenroth D, Beutinger R, Lupp A, Fleck C. Effects of a therapy with losartan and quinaprilat on the progression of chronic renal failure in rats after a single dose of uranyl nitrate or 5/6 nephrectomy. Exp Toxicol Pathol. 2003 Jun;54(5-6):359-66. doi: 10.1078/0940-2993-00271. PMID: 12877346. 12: Yamada S, Muraoka I, Kato K, Hiromi Y, Takasu R, Seno H, Kawahara H, Nabeshima T. Elimination kinetics of quinaprilat and perindoprilat in hypertensive patients with renal failure on haemodialysis. Biol Pharm Bull. 2003 Jun;26(6):872-5. doi: 10.1248/bpb.26.872. PMID: 12808303. 13: Chen X, Minatoguchi S, Wang N, Arai M, Lu C, Uno Y, Misao Y, Takemura G, Fujiwara H. Quinaprilat reduces myocardial infarct size involving nitric oxide production and mitochondrial KATP channel in rabbits. J Cardiovasc Pharmacol. 2003 Jun;41(6):938-45. doi: 10.1097/00005344-200306000-00017. PMID: 12775974. 14: Hayase N, Satomi M, Hara A, Awaya T, Shimizu K, Matsubara K. Protective effects of quinaprilat and trandolaprilat, active metabolites of quinapril and trandolapril, on hemolysis induced by lysophosphatidylcholine in human erythrocytes. Biol Pharm Bull. 2003 May;26(5):712-6. doi: 10.1248/bpb.26.712. PMID: 12736518. 15: Lazar HL. Quinaprilat during cardioplegic arrest. J Thorac Cardiovasc Surg. 2003 Apr;125(4):974-5. doi: 10.1067/mtc.2003.337. PMID: 12698173. 16: Korn P, Kröner A, Schirnhofer J, Hallström S, Bernecker O, Mallinger R, Franz M, Gasser H, Wolner E, Podesser BK. Quinaprilat during cardioplegic arrest in the rabbit to prevent ischemia-reperfusion injury. J Thorac Cardiovasc Surg. 2002 Aug;124(2):352-60. doi: 10.1067/mtc.2002.121676. PMID: 12167796. 17: Abbara Ch, Aymard G, Hinh S, Diquet B. Simultaneous determination of quinapril and its active metabolite quinaprilat in human plasma using high- performance liquid chromatography with ultraviolet detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Jan 25;766(2):199-207. doi: 10.1016/s0378-4347(01)00474-1. PMID: 11824807. 18: Prieto JA, Alonso RM, Jiménez RM. Determination of the angiotensin- converting enzyme inhibitor quinapril and its metabolite quinaprilat in pharmaceuticals and urine by capillary zone electrophoresis and solid-phase extraction. Electrophoresis. 2002 Jan;23(1):102-9. doi: 10.1002/1522-2683(200201)23:1<102::AID-ELPS102>3.0.CO;2-C. PMID: 11824610. 19: Begg EJ, Robson RA, Gardiner SJ, Hudson LJ, Reece PA, Olson SC, Posvar EL, Sedman AJ. Quinapril and its metabolite quinaprilat in human milk. Br J Clin Pharmacol. 2001 May;51(5):478-81. doi: 10.1046/j.1365-2125.2001.01327.x. PMID: 11422007; PMCID: PMC2014479. 20: Prieto JA, Alonso RM, Jiménez RM, Blanco A. Solid-phase extraction and high- performance liquid chromatography applied to the determination of quinapril and its metabolite quinaprilat in urine. J Chromatogr Sci. 2001 Apr;39(4):153-9. doi: 10.1093/chromsci/39.4.153. PMID: 11318067.