WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H564690
CAS#: 82768-85-2 (free base)
Description: 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.
Hodoodo Cat#: H564690
Name: Quinaprilat free base
CAS#: 82768-85-2 (free base)
Chemical Formula: C23H26N2O5
Exact Mass: 410.18
Molecular Weight: 410.470
Elemental Analysis: C, 67.30; H, 6.38; N, 6.82; O, 19.49
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:
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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: | |
| In vitro protocol: | |
| In vivo protocol: |
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.
