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

MedKoo CAT#: 526074

CAS#: 1435786-09-6 (hydrate)

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.


Price and Availability

Size
Price

10mg
USD 350
Size
Price

25mg
USD 650
Size
Price

Quinaprilat, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 526074
Name: Quinaprilat hydrate
CAS#: 1435786-09-6 (hydrate)
Chemical Formula: C23H28N2O6
Exact Mass: 410.1842
Molecular Weight: 428.485
Elemental Analysis: C, 64.47; H, 6.59; N, 6.54; O, 22.40


Related CAS #: 1435786-09-6 (hydrate)   82768-85-2 (anhydrous)    

Synonym: Quinaprilat; BRN 5653070; CI 928; CI-928.

IUPAC/Chemical Name: (S)-2-(((S)-1-carboxy-3-phenylpropyl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrate

InChi Key: OFYSYEOWQQCPEU-ZAFWUOJLSA-N

InChi Code: InChI=1S/C23H26N2O5.H2O/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);1H2/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.[H]O[H]


Technical Data

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).

Harmonized System Code:
293490


References

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. PubMed PMID: 24175935.

2: 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. Review. PubMed PMID: 19761414.

3: 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. PubMed PMID: 21083190.

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. PubMed PMID: 19135197.

5: 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. PubMed PMID: 19016233.

6: 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. PubMed PMID: 18723407.

7: 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. Epub 2006 Nov 13. PubMed PMID: 17098309.

8: 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. PubMed PMID: 15223904.

9: 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. PubMed PMID: 14973800.

10: 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. PubMed PMID: 12877346.

11: 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. PubMed PMID: 12808303.

12: 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. PubMed PMID: 12775974.

13: 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. PubMed PMID: 12736518.

14: Lazar HL. Quinaprilat during cardioplegic arrest. J Thorac Cardiovasc Surg. 2003 Apr;125(4):974-5. PubMed PMID: 12698173.

15: 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. PubMed PMID: 12167796.

16: 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. PubMed PMID: 11824807.

17: 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. PubMed PMID: 11824610.

18: 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. PubMed PMID: 11422007; PubMed Central PMCID: PMC2014479.

19: 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. PubMed PMID: 11318067.

20: Houben AJ, Kroon AA, de Haan CH, Fuss-Lejeune MJ, de Leeuw PW. Quinaprilat-induced vasodilatation in forearm vasculature of patients with essential hypertension: comparison with enalaprilat. Cardiovasc Drugs Ther. 2000 Dec;14(6):657-63. PubMed PMID: 11300367.