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Fosinopril Sodium (also known as SQ28555), the ester prodrug offosinoprilat, is a potent angiotensin-converting enzyme (ACE) inhibitor that is used for the treatment of hypertension and some types of chronic heart failure. Fosinopril Sodium is a phosphinic acid-containing ACEinhibitor that is effective in the treatment of hypertension. Fosinoprilbinds to the active site of ACE via targeting the zinc ions with its phosphinic acid moiety.
Physicochemical Properties
| Molecular Formula | C30H45NO7P.NA |
| Molecular Weight | 585.64 |
| Exact Mass | 563.301 |
| CAS # | 88889-14-9 |
| Related CAS # | Fosinopril;98048-97-6 |
| PubChem CID | 23681451 |
| Appearance | White to off-white solid powder |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 705.7±70.0 °C at 760 mmHg |
| Melting Point | 196-198ºC |
| Flash Point | 380.6±35.7 °C |
| Vapour Pressure | 0.0±2.4 mmHg at 25°C |
| Index of Refraction | 1.532 |
| LogP | 6.09 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 15 |
| Heavy Atom Count | 40 |
| Complexity | 857 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2C[C@@H](C[C@H]2C(=O)[O-])C3CCCCC3.[Na+] |
| InChi Key | TVTJZMHAIQQZTL-HREVRLCXSA-M |
| InChi Code | InChI=1S/C30H46NO7P.Na/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);/q;+1/p-1/t25-,26+,30?,39?;/m1./s1 |
| Chemical Name | sodium;(2S,4S)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate |
| Synonyms | SQ-28,555;SQ 28,555; SQ 28555; SQ-28,555; SQ-28555; SQ28,555; SQ28555; Monopril; Staril; Dynacil; Fosinil; Tenso Stop; Tensocardil; Sodium, Fosinopril; Staril; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Co-sedimentation of liposomes and recombinant LPLA2 is partially inhibited by fosinopril (0, 1, 10, 33, 100 μM; 30 min) [1]. The soluble esterase activity of LPLA2 is not inhibited by fosinopril (250 nM) [1]. With a Ki value of 1.675 μM, fosinopril (0.372, 0.744, 1.116 μM) inhibits ACE activity in a non-competitive manner [2]. |
| ln Vivo | By decreasing the levels of lactate dehydrogenase (LDH) and creatine kinase (CK), fosinopril (oral; 4.67 mg/kg; 4 weeks) counteracts cardiac dysfunction and structural alterations [3]. In rat models of acute myocardial infarction, fosinopril (oral; 4.67 mg/kg; 4 weeks) reduces the expression of cleaved-caspase 3 and cardiomyocyte apoptosis. |
| Animal Protocol |
Animal/Disease Models: Acute myocardial infarction (AMI) rat model after heart failure (SPF grade SD (SD (Sprague-Dawley)) rat, 265±15g) [3] Doses: 4.67mg/kg Route of Administration: oral; 4-week Experimental Results: Combats cardiac dysfunction and structural changes and inhibits apoptosis. |
| References |
[1]. Ondetti, M.A., Structural relationships of angiotensin converting-enzyme inhibitors to pharmacologic activity. Circulation, 1988. 77(6 Pt 2): p. I74-8. [2]. Piepho, R.W., Overview of the angiotensin-converting-enzyme inhibitors. Am J Health Syst Pharm, 2000. 57 Suppl 1: p. S3-7. [3]. The hemodynamic effects of long-term ACE inhibition with fosinopril in patients with heart failure. Fosinopril Hemodynamics Study Group. Am J Ther, 1999. 6(4): p. 181-9. |
| Additional Infomation |
Fosinopril sodium is the sodium salt of fosinopril. It is used for the treatment of hypertension and heart failure. A pro-drug, its phosphinate ester group is hydrolysed in vivo to give the corresponding phosphininc acid, fosinoprilat, which is the active metabolite. It has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, a prodrug and an antihypertensive agent. It contains a fosinopril(1-). Fosinopril Sodium is the sodium salt of fosinopril, a phosphinic acid-containing angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Fosinopril sodium is an ester prodrug that is hydrolysed by esterases to its active metabolite fosinoprilat. Fosinoprilat specifically and competitively inhibits angiotensin-converting enzyme thereby decreasing the formation of the potent vasoconstrictor angiotensin II, resulting in diminished vasopressor activity. In addition, angiotensin II-mediated aldosterone secretion by adrenal cortex is decreased, which results in a decrease of sodium retention and an increase of serum potassium. (NCI05) 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. See also: Fosinopril (has active moiety); Fosinoprilat (has active moiety); Fosinopril sodium; hydrochlorothiazide (component of). |
Solubility Data
| Solubility (In Vitro) | DMSO:<1 mg/mL Water:117 mg/mL (199.8 mM) Ethanol:4 mg/mL (6.8 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 9.09 mg/mL (15.52 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7075 mL | 8.5377 mL | 17.0753 mL | |
| 5 mM | 0.3415 mL | 1.7075 mL | 3.4151 mL | |
| 10 mM | 0.1708 mL | 0.8538 mL | 1.7075 mL |