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MedKoo Cat#: 597878 | Name: Fosinopril

Description:

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

Fosinopril is a phosphinic acid-containing angiotensin-converting enzyme inhibitor that is effective in the treatment of hypertension. It is a prodrug that is converted to its active metabolite fosinoprilat.

Chemical Structure

Fosinopril
Fosinopril
CAS#98048-97-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 597878

Name: Fosinopril

CAS#: 98048-97-6 (free acid)

Chemical Formula: C30H46NO7P

Exact Mass: 563.3012

Molecular Weight: 563.67

Elemental Analysis: C, 63.93; H, 8.23; N, 2.48; O, 19.87; P, 5.49

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
98048-97-6 (free acid) 88889-14-9 (sodium)
Synonym
Fosinopril; Fosinopril impurity C; Fosenopril; Fozitec
IUPAC/Chemical Name
(2S,4S)-4-cyclohexyl-1-(2-(((S)-2-methyl-1-(propionyloxy)propoxy)(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylic acid
InChi Key
BIDNLKIUORFRQP-AJTMIRJTSA-N
InChi Code
InChI=1S/C30H46NO7P/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35)/t25-,26+,30+,39?/m1/s1
SMILES Code
O=C([C@H]1N(C(CP(CCCCC2=CC=CC=C2)(O[C@H](OC(CC)=O)C(C)C)=O)=O)C[C@H](C3CCCCC3)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
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 563.67 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: Huang ZB, Deng CY, Lin MH, Yuan GY, Wu W. Fosinopril improves the electrophysiological characteristics of left ventricular hypertrophic myocardium in spontaneously hypertensive rats. Naunyn Schmiedebergs Arch Pharmacol. 2014 Nov;387(11):1037-44. doi: 10.1007/s00210-014-1024-y. Epub 2014 Jul 27. PubMed PMID: 25064464. 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: Huang ZB, Fang C, Lin MH, Yuan GY, Zhou SX, Wu W. Effect of fosinopril on the transient outward potassium current of hypertrophied left ventricular myocardium in the spontaneously hypertensive rat. Naunyn Schmiedebergs Arch Pharmacol. 2014 May;387(5):419-25. doi: 10.1007/s00210-014-0956-6. Epub 2014 Jan 19. PubMed PMID: 24441766. 5: Araiza-Saldaña CI, Pedraza-Priego EF, Torres-López JE, Rocha-González HI, Castañeda-Corral G, Hong-Chong E, Granados-Soto V. Fosinopril Prevents the Development of Tactile Allodynia in a Streptozotocin-Induced Diabetic Rat Model. Drug Dev Res. 2015 Dec;76(8):442-9. doi: 10.1002/ddr.21280. Epub 2015 Sep 9. PubMed PMID: 26349482. 6: Huang H, Hu L, Lin J, Zhu X, Cui W, Xu W. Effect of fosinopril on chemerin and VEGF expression in diabetic nephropathy rats. Int J Clin Exp Pathol. 2015 Sep 1;8(9):11470-4. eCollection 2015. PubMed PMID: 26617877; PubMed Central PMCID: PMC4637693. 7: Green BR, Bain LJ. Mrp2 is involved in the efflux and disposition of fosinopril. J Appl Toxicol. 2013 Jun;33(6):458-65. doi: 10.1002/jat.1767. Epub 2011 Nov 17. PubMed PMID: 22095822. 8: Yang S, Li R, Tang L, Qu X, Ge G, Ma J, Liu H, Qiao Z, Fang W. TLR4-mediated anti-atherosclerosis mechanisms of angiotensin-converting enzyme inhibitor--fosinopril. Cell Immunol. 2013 Sep-Oct;285(1-2):38-41. doi: 10.1016/j.cellimm.2013.08.003. Epub 2013 Aug 20. PubMed PMID: 24044965. 9: Narayanam M, Singh S. Characterization of stress degradation products of fosinopril by using LC-MS/TOF, MS(n) and on-line H/D exchange. J Pharm Biomed Anal. 2014 Apr;92:135-43. doi: 10.1016/j.jpba.2014.01.010. Epub 2014 Jan 22. PubMed PMID: 24518132. 10: Deb D, Bairy KL, Nayak V, Rao M. Comparative Effect of Lisinopril and Fosinopril in Mitigating Learning and Memory Deficit in Scopolamine-Induced Amnesic Rats. Adv Pharmacol Sci. 2015;2015:521718. doi: 10.1155/2015/521718. Epub 2015 Aug 2. PubMed PMID: 26300914; PubMed Central PMCID: PMC4537708. 11: Zhang YC, Tang Y, Zhang M, Chen J, Zhou Q, Sun YG, Chen MT, Xu WP. Fosinopril attenuates the doxorubicin-induced cardiomyopathy by restoring the function of sarcoplasmic reticulum. Cell Biochem Biophys. 2012 Dec;64(3):205-11. doi: 10.1007/s12013-012-9386-6. PubMed PMID: 22729889. 12: Khukhlina OS, Mandryk OIe, Drozd VIu, Haĭdychuk VS, Kosar LIu. [The use of complex tools ezetimibe, hepadyfu fosinopril and correction of blood pressure and endothelial dysfunction in patients with nonalcoholic steatohepatitis and essential hypertension stage II]. Wiad Lek. 2014;67(2 Pt 2):269-72. Ukrainian. PubMed PMID: 25796845. 13: Pouwels KB, Visser ST, Hak E. Effect of pravastatin and fosinopril on recurrent urinary tract infections. J Antimicrob Chemother. 2013 Mar;68(3):708-14. doi: 10.1093/jac/dks419. Epub 2012 Oct 30. PubMed PMID: 23111852; PubMed Central PMCID: PMC3566666. 14: Sarro GD, Paola ED, Gratteri S, Gareri P, Rispoli V, Siniscalchi A, Tripepi G, Gallelli L, Citraro R, Russo E. Fosinopril and zofenopril, two angiotensin-converting enzyme (ACE) inhibitors, potentiate the anticonvulsant activity of antiepileptic drugs against audiogenic seizures in DBA/2 mice. Pharmacol Res. 2012 Mar;65(3):285-96. doi: 10.1016/j.phrs.2011.11.005. Epub 2011 Nov 17. PubMed PMID: 22107891. 15: Choudary J, Kini SG, Ranganath Pai Karkala S, Mubeen M. Docking studies and biological activity of fosinopril analogs. Int J Med Chem. 2014;2014:721834. doi: 10.1155/2014/721834. Epub 2014 Jul 6. PubMed PMID: 25383221; PubMed Central PMCID: PMC4207403. 16: Singh RG, Rajak M, Ghosh B; Usha, Agrawal A, Dubey GP. Comparative evaluation of fosinopril and herbal drug Dioscorea bulbifera in patients of diabetic nephropathy. Saudi J Kidney Dis Transpl. 2013 Jul;24(4):737-42. PubMed PMID: 23816723. 17: Brouwers FP, Asselbergs FW, Hillege HL, de Boer RA, Gansevoort RT, van Veldhuisen DJ, van Gilst WH. Long-term effects of fosinopril and pravastatin on cardiovascular events in subjects with microalbuminuria:Ten years of follow-up of Prevention of Renal and Vascular End-stage Disease Intervention Trial (PREVEND IT). Am Heart J. 2011 Jun;161(6):1171-8. doi: 10.1016/j.ahj.2011.03.028. Epub 2011 May 11. PubMed PMID: 21641365. 18: Sbârcea L, Udrescu L, Drăgan L, Trandafirescu C, Szabadai Z, Bojiţă M. Fosinopril-cyclodextrin inclusion complexes: phase solubility and physicochemical analysis. Pharmazie. 2011 Aug;66(8):584-9. PubMed PMID: 21901980. 19: Sharma S, Deitchman D, Eni JS, Gelperin K, Ilgenfritz JP, Blumenthal M. The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther. 1999 Jul;6(4):181-9. PubMed PMID: 11329095. 20: Wagstaff AJ, Davis R, McTavish D. Fosinopril: a reappraisal of its pharmacology and therapeutic efficacy in essential hypertension. Drugs. 1996 May;51(5):777-91. Review. PubMed PMID: 8861547.