105107-84-4

Basic information

• Product Name: cis-4-Phenylthio-L-proline hydrochloride
• Synonyms: Cis-4-Phenylthio-L-proline hydrochloride;(4S)-4-(Phenylthio)-L-proline hydrochloride;Cis-4-phenylthio-L-proline;L-Proline,4-(phenylthio)-, hydrochloride (1:1), (4S);cis-4-Phenylthio-L-Proline HCl;(2S,4S)-4-(phenylthio)pyrrolidine-2-carboxylic acid hydrochloride;cis-4-Phenylthio-L-proline hydrochloride(Zofenopril calcium)
• CAS NO: 105107-84-4
• Molecular Formula: BrH*C₁₁H₁₃NO₂S
• Molecular Weight: 259.75
• Mol File: 105107-84-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• CAS DataBase Reference: cis-4-Phenylthio-L-proline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: cis-4-Phenylthio-L-proline hydrochloride(105107-84-4)
• EPA Substance Registry System: cis-4-Phenylthio-L-proline hydrochloride(105107-84-4)

Safety Data

• Hazardous Substances Data: 105107-84-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Manufacturing:
cis-4-Phenylthio-L-proline hydrochloride is used as a reference impurity for the drug Zofenopril (Z587000). Its presence is crucial for ensuring the purity and quality of the final drug product, as it helps in monitoring and controlling the manufacturing process to meet regulatory standards.
Used in Quality Control and Analysis:
In the pharmaceutical industry, cis-4-Phenylthio-L-proline hydrochloride is utilized as a benchmark for quality control and analytical testing. It aids in the development of methods to detect and quantify impurities, thereby ensuring the safety, efficacy, and consistency of the drug Zofenopril.
Used in Research and Development:
cis-4-Phenylthio-L-proline hydrochloride serves as a valuable compound in the research and development of new pharmaceuticals and drug formulations. Its unique chemical properties and role as an impurity in Zofenopril make it a useful tool for studying drug synthesis, stability, and potential interactions with other compounds.

InChI:InChI=1/C11H13NO2S.ClH/c13-11(14)10-6-9(7-12-10)15-8-4-2-1-3-5-8;/h1-5,9-10,12H,6-7H2,(H,13,14);1H/t9-,10-;/m0./s1

Upstream product

• 83623-88-5 (2S,4S)-4-(phenylsulfanyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 
• 57653-38-0 N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester 
• 108-98-5 thiophenol 
• 75176-28-2 N-(benzyloxycarbonyl)-cis-4-(phenylthio)-L-proline 

Downstream Products

• 81872-10-8 zofenopril 
• 83552-05-0 (2S,4S)-1-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-4-phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester 
• 83552-06-1 [1(S),4S]-1-[N-(1-Carboxy-3-phenylpropyl)-L-alanyl]-4-(phenylthio)-L-prolin 
• 83552-04-9 (2S,4S)-4-Phenylsulfanyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride 

Relevant articles and documents

PYRROLIDINE ANALOGUE FOR PREVENTING NEUROGENIC PAIN AND METHOD FOR PRODUCTION THEREOF

[Problems] To provide a pyrrolidine analogue having an inhibitory activity on the induction of allodynia, a method for producing the pyrrolidine analogue, and an agent for preventing a neurogenic pain. [Means for Solving the Problems] A pyrrolidine analog

Angiotensin-converting enzyme inhibitors. Mercaptan, carboxyalkyl dipeptide, and phosphinic acid inhibitors incorporating 4-substituted prolines

Analogues of captopril, enalaprilat, and the phosphinic acid [[hydroxy(4-phenylbutyl)phosphinyl]acetyl)-L-proline incorporating 4-substituted proline derivatives have been synthesized and evaluated as inhibitors of angiotensin-converting enzyme (ACE) in vitro and in vivo. The 4-substituted prolines, incorporating alkyl, aryl, alkoxy, aryloxy, alkylthio, and arylthio substituents were prepared from derivatives of 4-hydroxy- and 4-ketoproline. In general, analogues of all three classes of inhibitors with hydrophobic substituents on proline were more potent in vitro than the corresponding unsubstituted proline compounds. 4-Substituted analogues of captopril showed greater potency and duration of action than the parent compound as inhibitors of the angiotensin I induced pressor response in normotensive rats. The S-benzoyl derivative of cis-4-(phenylthio)captopril, zofenopril, was found to be one of the most potent compounds of this class and is now being evaluated clinically as an antihypertensive agent. In the phosphinic acid series, the 4-ethylenethioketal and trans-4-cyclohexyl derivatives were found to be the most potent compounds in vitro and in vivo. A prodrug of the latter compound, fosinopril, is also being evaluated in clinical trials.