CID 9912532

Base Information

• Chemical Name: CID 9912532
• CAS No.: 81938-43-4
• Molecular Formula: 2(C22H22NO4S2)^.Ca
• Molecular Weight: 897.184
• European Community (EC) Number: 682-603-4
• NCI Thesaurus Code: C82220
• Mol file: 81938-43-4.mol

Synonyms:ZOFENOPRIL CALCIUM;81938-43-4;SCHEMBL388350

Chemical Property of CID 9912532

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline solid
• Vapor Pressure: 1.38E-17mmHg at 25°C
• Melting Point: >250 °C
• Boiling Point: 646.3 °C at 760 mmHg
• Flash Point: 344.7 °C
• PSA: 228.56000
• Density: 1.34 g/cm³
• LogP: 7.80660
• Storage Temp.: Refrigerator
• Solubility.: DMSO: >5mg/mL
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 469.0694414
• Heavy Atom Count: 30
• Complexity: 587

Purity/Quality:

99% ^*data from raw suppliers

Zofenopril Calcium Salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CSC(=O)C1=CC=CC=C1)C(=O)N2CC(CC2C(=O)O)SC3=CC=CC=C3.[Ca]
• Isomeric SMILES: C[C@H](CSC(=O)C1=CC=CC=C1)C(=O)N2C[C@H](C[C@H]2C(=O)O)SC3=CC=CC=C3.[Ca]
• Recent EU Clinical Trials: Interventional clinical trial to assess efficacy and safety of the extemporaneous combination of Zofenopril calcium and amlodipine in grade 1-2 hypertensive patients versus each monotherapy
• Uses: ACEI (angiotensin-converting enzyme inhibitors) class of antihypertensive drugs Angiotensin-converting enzyme ACE inhibitor. A prodrug that is de-esterified to the active inhibitor, the sulfhydryl group containing metabolite, Zofenoprilat adenosine A2a receptor agonist
• Description: Zofenopril is a prodrug form of the angiotensin-converting enzyme (ACE) inhibitor zofenoprilat. Zofenopril is hydrolyzed by cardiac esterases in vivo to form zofenoprilat. It inhibits ACE with an IC50 value of 0.9 nM in heart tissue homogenates and inhibits cardiac ACE activity in isolated perfused rat hearts. It reduces mean arterial blood pressure in two kidney-one clip renal hypertensive (2K-1C) rats and spontaneously hypertensive rats (SHRs) when administered at doses of 2.2, 6.6, and 22 mg/kg. Unlike the ACE inhibitor ramipril , zofenopril does not affect bronchoalveolar lavage fluid (BALF) levels of bradykinin or prostaglandin E2 (PGE2; ) or increase coughing induced by citric acid in guinea pigs. Zofenopril calcium was introduced as a second-generation angiotensinconverting enzyme (ACE) inhibitor for the treatment of acute myocardial infarction. Zofenopril, rapidly hydrolyzed by cardiac esterase, is actually a S-benzoyl prodrug of the active component zofenopril-sulfhydryl (zofenoprilat), the latter being the ACE inhibitor responsible for the improvement of postischemic contractile function and for the reduction of cardiac cell death. It was suggested that ACE inhibition alone was not sufficient to explain the cardioprotective effects; the antioxidant properties demonstrated in vitro and in viva could partly explain the strong anti-ischemic effects. In rats with CHF after myocardial infarction, zofenopril attenuated ventricular enlargement and cardiac hypertrophy. It was also shown in isolated globally ischemic rat hearts that the cardioprotective effect of zofenopril was stereoselective. Clinical studies in healthy volunteers comparing zofenopril with enalapril demonstrated that the rate of hydrolysis of the former was faster; at 30 or 60 mg, ACE was completely inhibited in most volunteers until 12h after administration. In patients with anterior acute myocardial infarction, a g-week treatment with zofenopril significantly reduced the incidence of death or severe CHF and also improved the chance of surviving the next year.
• Therapeutic Function: Antihypertensive

Technology Process of CID 9912532

There total 6 articles about CID 9912532 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1S,4S)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-(phenylthio)-L-proline potassium salt (81938-42-3) → calcium (2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate (81938-43-4)

Guidance literature:

With calcium chloride; In water; at 25 - 60 ℃; for 3 - 24h; Product distribution / selectivity;

Reference yield:

(4S)-1((2S)-3-(benzoylthio)-2-methylpropionyl)-4-(phenylthio)-L-proline, dicyclohexylamine salt (81938-38-7) → calcium (2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate (81938-43-4)

Guidance literature:

With calcium chloride; In methanol; water; at 55 - 85 ℃; for 3h; Product distribution / selectivity;

Reference yield:

zofenopril (81872-10-8) → calcium (2S,4S)-1-[(2S)-3-(benzoylsulfanyl)-2-methylpropanoyl]-4-(phenylsulfanyl)pyrrolidine-2-carboxylate (81938-43-4)

Guidance literature:

zofenopril; With sodium hydroxide; In water; at 40 - 45 ℃; pH=8 - 8.5;

With calcium(II) chloride dihydrate; In water; at 40 - 58 ℃; Product distribution / selectivity;

upstream raw materials:

(4S)-1((2S)-3-(benzoylthio)-2-methylpropionyl)-4-(phenylthio)-L-proline, dicyclohexylamine salt

calcium chloride

(1S,4S)-1-<3-(benzoylthio)-2-methyl-1-oxopropyl>-4-(phenylthio)-L-proline potassium salt

zofenopril

Downstream raw materials:

(4S)-1-[(S)-3-benzoylthio-2-methylpropanoyl]-4-phenylthio-L-proline methyl ester

Refernces

• 1、 -. "ZOFENOPRIL CALCIUM". Page/Page column 3. . Retrieved 2009/07/18.
• 2、 -. "ZOFENOPRIL CALCIUM". Page/Page column 9-10. . Retrieved 2008/06/13.