198342-23-3

198342-23-3 structure

Name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid,hydrochloride
Chemical Name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid,hydrochloride
CAS Number: 198342-23-3
Molecular Formula: C₉H₁₆ClNO₃S
Molecular Weight: 253.74600
Catalog: Signaling Pathways Metabolic Enzyme/Protease Angiotensin-converting Enzyme (ACE)
Create Date: 2017-12-30 20:59:06
Modify Date: 2025-08-25 11:21:25
Captopril (SQ 14225) hydrochloride, antihypertensive agent, is a thiol-containing competitive, orally active angiotensin-converting enzyme (ACE) inhibitor (IC50=0.025 μM) and has been widely used for research of hypertension and congestive heart failure. Captopril hydrochloride is also a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 of 7.9 μM[1][2][3].

Name	(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid,hydrochloride
Synonyms	L-Proline,1-[(2S)-3-mercapto-2-methyl-1-oxopropyl]-,hydrochloride

Description	Captopril (SQ 14225) hydrochloride, antihypertensive agent, is a thiol-containing competitive, orally active angiotensin-converting enzyme (ACE) inhibitor (IC50=0.025 μM) and has been widely used for research of hypertension and congestive heart failure. Captopril hydrochloride is also a New Delhi metallo-β-lactamase-1 (NDM-1) inhibitor with an IC50 of 7.9 μM[1][2][3].
Related Catalog	Research Areas >> Cardiovascular Disease Signaling Pathways >> Metabolic Enzyme/Protease >> Angiotensin-converting Enzyme (ACE)
Target	ACE[1]
In Vitro	Captopril (SQ 14225) hydrochloride has been shown to have similar morbidity and mortality benefits to those of diuretics and beta-blockers in hypertensive patients. Captopril hydrochloride has been shown to delay the progression of diabetic nephropathy, and enalapril and lisinopril prevent the development of nephropathy in normoalbuminuric patients with diabetes[4]. An equimolar ratio of the cis and trans states of Captopril hydrochloride exists in solution and that the enzyme selects only the trans state of the inhibitor that presents architectural and stereoelectronic complementarity with its substrate binding groove[5].
References	[1]. Afrin S, et al. Eritadenine from Edible Mushrooms Inhibits Activity of Angiotensin Converting Enzyme in Vitro. J Agric Food Chem. 2016;64(11):2263-2268. [2]. Esmaeili S, et al. Captopril/enalapril inhibit promiscuous esterase activity of carbonic anhydrase at micromolar concentrations: An in vitro study. Chem Biol Interact. 2017;265:24-35. [3]. Li N, et al. Simplified captopril analogues as NDM-1 inhibitors. Bioorg Med Chem Lett. 2014;24(1):386-389. [4]. Tzakos, A.G., et al., The molecular basis for the selection of captopril cis and trans conformations by angiotensin I converting enzyme. Bioorg Med Chem Lett, 2006. 16(19): p. 5084-7. [5]. Song, J.C. and C.M. White, Clinical pharmacokinetics and selective pharmacodynamics of new angiotensin converting enzyme inhibitors: an update. Clin Pharmacokinet, 2002. 41(3): p. 207-24.

Molecular Formula	C₉H₁₆ClNO₃S
Molecular Weight	253.74600
Exact Mass	253.05400
PSA	96.41000
LogP	1.36780

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