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MedKoo Cat#: 597877 | Name: Fosinoprilat
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Description:

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

Fosinoprilat is an active phosphinic acid metabolite of prodrug fosenopril, which is activated by esterases in vivo; binds zinc with phosphinic acid group.

Chemical Structure

Fosinoprilat
Fosinoprilat
CAS#95399-71-6

Theoretical Analysis

MedKoo Cat#: 597877

Name: Fosinoprilat

CAS#: 95399-71-6

Chemical Formula: C23H34NO5P

Exact Mass: 435.2175

Molecular Weight: 435.50

Elemental Analysis: C, 63.43; H, 7.87; N, 3.22; O, 18.37; P, 7.11

Price and Availability

Size Price Availability Quantity
5mg USD 385.00 2 Weeks
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Related CAS #
No Data
Synonym
Fosinoprilat; Fosinopril diacid; fosfenopril; Fosinoprilic acid; SQ 27,519; SQ-27,519; SQ27,519; SQ-27519; SQ27519; SQ 27519
IUPAC/Chemical Name
(2S,4S)-4-cyclohexyl-1-(2-(hydroxy(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylic acid
InChi Key
WOIWWYDXDVSWAZ-RTWAWAEBSA-N
InChi Code
InChI=1S/C23H34NO5P/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29)/t20-,21+/m1/s1
SMILES Code
O=C(O)[C@H]1N(C(CP(CCCCC2=CC=CC=C2)(O)=O)=O)C[C@H](C3CCCCC3)C1
Appearance
Solid powder
Purity
>95% (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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 435.50 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.

Recalculate based on batch purity %
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
1: Xue K, Li G, Sun X, Hu Y, Hu L, Huang J, Si L. Simultaneous quantification of fosinopril and its active metabolite fosinoprilat in rat plasma by UFLC-MS/MS: Application of formic acid in the stabilization of an ester-containing drug. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 May 15;990:141-9. doi: 10.1016/j.jchromb.2015.03.028. Epub 2015 Apr 3. PubMed PMID: 25875586. 2: Yang S, Li R, Qu X, Tang L, Ge G, Fang W, Qiao Z, Ma J, Hou Y, Liu H. Fosinoprilat alleviates lipopolysaccharide (LPS)-induced inflammation by inhibiting TLR4/NF-κB signaling in monocytes. Cell Immunol. 2013 Jul-Aug;284(1-2):182-6. doi: 10.1016/j.cellimm.2013.06.009. Epub 2013 Jun 28. PubMed PMID: 24036412. 3: Uutela P, Monto M, Iso-Mustajärvi I, Madetoja M, Yliperttula M, Ketola RA. Identification of metabolites of fosinopril produced by human and rat liver microsomes with liquid chromatography-mass spectrometry. Eur J Pharm Sci. 2014 Mar 12;53:86-94. doi: 10.1016/j.ejps.2013.12.009. Epub 2013 Dec 21. PubMed PMID: 24365260. 4: Hu OY, Ding PY, Huang CS, Hwang GM, Chu KM. Pharmacokinetics of fosinoprilat in Chinese and whites after intravenous administration. J Clin Pharmacol. 1997 Sep;37(9):834-40. PubMed PMID: 9549638. 5: Jancic B, Ivanovic D, Medenica M, Malenovic A, Dimkovic N. Development of liquid chromatographic method for fosinoprilat determination in human plasma using microemulsion as eluent. J Chromatogr A. 2005 Sep 23;1088(1-2):187-92. PubMed PMID: 16130750. 6: Greenbaum R, Zucchelli P, Caspi A, Nouriel H, Paz R, Sclarovsky S, O'Grady P, Yee KF, Liao WC, Mangold B. Comparison of the pharmacokinetics of fosinoprilat with enalaprilat and lisinopril in patients with congestive heart failure and chronic renal insufficiency. Br J Clin Pharmacol. 2000 Jan;49(1):23-31. PubMed PMID: 10606834; PubMed Central PMCID: PMC2014892. 7: Gehr TW, Sica DA, Grasela DM, Duchin KL. The pharmacokinetics and pharmacodynamics of fosinopril in haemodialysis patients. Eur J Clin Pharmacol. 1993;45(5):431-6. PubMed PMID: 8112372. 8: Ford NF, Lasseter KC, Van Harken DR, Hammett JL, Raymond R, Manning J. Single-dose and steady-state pharmacokinetics of fosinopril and fosinoprilat in patients with hepatic impairment. J Clin Pharmacol. 1995 Feb;35(2):145-50. PubMed PMID: 7751424. 9: Jemal M, Huang M, Mao Y, Whigan D, Schuster A. Liquid chromatography/electrospray tandem mass spectrometry method for the quantitation of fosinoprilat in human serum using automated 96-well solid-phase extraction for sample preparation. Rapid Commun Mass Spectrom. 2000;14(12):1023-8. PubMed PMID: 10861982. 10: Jemal M, Mulvana DE. Liquid chromatographic-electrospray tandem mass spectrometric method for the simultaneous quantitation of the prodrug fosinopril and the active drug fosinoprilat in human serum. J Chromatogr B Biomed Sci Appl. 2000 Mar 10;739(2):255-71. PubMed PMID: 10755370. 11: Janci B, Medenica M, Ivanović D, Malenović A, Marković S. Microemulsion liquid chromatographic method for characterisation of fosinopril sodium and fosinoprilat separation with chemometrical support. Anal Bioanal Chem. 2005 Oct;383(4):687-94. Epub 2005 Sep 30. PubMed PMID: 16195875. 12: Cui S, Feng F, Ma M, Liu H, Chen Y. Development and validation of liquid chromatography-tandem mass spectrometric method for simultaneous determination of fosinopril and its active metabolite fosinoprilat in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jul 1;854(1-2):143-51. Epub 2007 Apr 25. PubMed PMID: 17482898. 13: O'Grady P, Yee KF, Lins R, Mangold B. Fosinopril/hydrochlorothiazide: single dose and steady-state pharmacokinetics and pharmacodynamics. Br J Clin Pharmacol. 1999 Sep;48(3):375-81. PubMed PMID: 10510149; PubMed Central PMCID: PMC2014346. 14: Hui KK, Duchin KL, Kripalani KJ, Chan D, Kramer PK, Yanagawa N. Pharmacokinetics of fosinopril in patients with various degrees of renal function. Clin Pharmacol Ther. 1991 Apr;49(4):457-67. PubMed PMID: 1826651. 15: Kostis JB, Garland WT, Delaney C, Norton J, Liao WC. Fosinopril: pharmacokinetics and pharmacodynamics in congestive heart failure. Clin Pharmacol Ther. 1995 Dec;58(6):660-5. PubMed PMID: 8529331. 16: Duchin KL, Waclawski AP, Tu JI, Manning J, Frantz M, Willard DA. Pharmacokinetics, safety, and pharmacologic effects of fosinopril sodium, an angiotensin-converting enzyme inhibitor in healthy subjects. J Clin Pharmacol. 1991 Jan;31(1):58-64. PubMed PMID: 1646240. 17: Murdoch D, McTavish D. Fosinopril. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in essential hypertension. Drugs. 1992 Jan;43(1):123-40. Review. PubMed PMID: 1372856. 18: Shionoiri H, Naruse M, Minamisawa K, Ueda S, Himeno H, Hiroto S, Takasaki I. Fosinopril. Clinical pharmacokinetics and clinical potential. Clin Pharmacokinet. 1997 Jun;32(6):460-80. Review. PubMed PMID: 9195116. 19: Auch-Schwelk W, Bossaller C, Claus M, Graf K, Gräfe M, Fleck E. Local potentiation of bradykinin-induced vasodilation by converting-enzyme inhibition in isolated coronary arteries. J Cardiovasc Pharmacol. 1992;20 Suppl 9:S62-7. PubMed PMID: 1282632. 20: Ranadive SA, Chen AX, Serajuddin AT. Relative lipophilicities and structural-pharmacological considerations of various angiotensin-converting enzyme (ACE) inhibitors. Pharm Res. 1992 Nov;9(11):1480-6. PubMed PMID: 1475237.