Temocapril

Modify Date: 2024-01-02 20:22:09

Temocapril Structure
Temocapril structure
Common Name Temocapril
CAS Number 111902-57-9 Molecular Weight 476.60900
Density 1.33 g/cm3 Boiling Point 717.4ºC at 760 mmHg
Molecular Formula C23H28N2O5S2 Melting Point >230ºC (dec)
MSDS N/A Flash Point 387.7ºC

 Use of Temocapril


Temocapril is an orally active angiotensin-converting enzyme (ACE) inhibitor. Temocapril can be used for the research of hypertension, congestive heart failure, acute myocardial infarction, insulin resistance, and renal diseases[1][2].

 Names

Name 2-[(2S)-6-[[(1S)-1-Ethoxycarbonyl-3-phenyl-propyl]amino]-5-oxo-2-thiophen-2-yl-1,4-thiazepan-4-yl]acetic acid
Synonym More Synonyms

 Temocapril Biological Activity

Description Temocapril is an orally active angiotensin-converting enzyme (ACE) inhibitor. Temocapril can be used for the research of hypertension, congestive heart failure, acute myocardial infarction, insulin resistance, and renal diseases[1][2].
Related Catalog
Target

Angiotensin-converting Enzyme (ACE)[1]

In Vitro Temocapril hydrochloride is a prodrug of the ACE inhibitor, Temocaprilat. Temocapril hydrochloride can be readily uptaken via the small intestine, and then be converted to its active metabolite (temocaprilat) by CES1 (human carboxylesterase 1) in the liver[1]. Temocapril hydrochloride (500 nM) reduces the inhibitory effects of RS (N-acetyltetradecapeptide renin substrate) and AngI (angiotensin) on neurogenic vasodilation in the spontaneously hypertensive rats (SHR)[2]. Temocapril hydrochloride (0.1-10 μM; 24 h) shows inductive effects on redox proteins thioredoxin (TRX) while no effect on antioxidant enzymes Cu/ZnSOD and Mn-SOD expressions[3]. Western Blot Analysis[3] Cell Line: Cultured neonatal rat cardiomyocytes Concentration: 0.1 μM, 1 μM, 10 μM Incubation Time: 24 hours Result: Enhanced redox proteins thioredoxin (TRX) expression 1.9-fold at 10 μM without affecting TRX2, Cu/Zn-SOD or Mn-SOD protein expression.
In Vivo Temocapril (10 mg/kg; p.o.; 21 d) enhances cardiomyocyte thioredoxin expression and ameliorates autoimmune myocarditis[3]. Temocapril (30 mg/kg; p.o.; daily; for 4 weeks) suppresses Angiotensin I-induced hypertension, plasma and renal ACE activity, but fails to reduce the level of Ang II in the kidney[4]. Animal Model: Experimental autoimmune myocarditis (EAM) rat model[3] Dosage: 10 mg/kg Administration: Oral gavage; administration by water; 21 days Result: Ameliorated EAM and prevented cellular proteins from oxidation. Enhanced cardiomyocyte redox regulatory protein TRX expression. Animal Model: Male Sprague Dawley rats[4] Dosage: 30 mg/kg Administration: Oral gavage, daily, for 4 weeks Result: Suppressed the blood pressure elevation induced by Ang I.
References

[1]. Fukami T, et al. In vitro evaluation of inhibitory effects of antidiabetic and antihyperlipidemic drugs on human carboxylesterase activities. Drug Metab Dispos. 2010 Dec;38(12):2173-8.

[2]. Kawasaki H, et al. Angiotensin inhibits neurotransmission of calcitonin gene-related peptide-containing vasodilator nerves in mesenteric artery of spontaneously hypertensive rats. J Pharmacol Exp Ther. 1998 Feb;284(2):508-15.

[3]. Yuan Z, et al. Temocapril treatment ameliorates autoimmune myocarditis associated with enhanced cardiomyocyte thioredoxin expression. Cardiovasc Res. 2002 Aug 1;55(2):320-8.

[4]. Ohnishi K, et al. Angiotensin-converting enzyme inhibitor does not suppress renal angiotensin II levels in angiotensin I-infused rats. J Pharmacol Sci. 2013;122(2):103-8.

 Chemical & Physical Properties

Density 1.33 g/cm3
Boiling Point 717.4ºC at 760 mmHg
Melting Point >230ºC (dec)
Molecular Formula C23H28N2O5S2
Molecular Weight 476.60900
Flash Point 387.7ºC
Exact Mass 476.14400
PSA 149.48000
LogP 3.30070
Storage condition -20℃

 Synthetic Route

~78%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Yanagisawa, Hiroaki; Ishihara, Sadao; Ando, Akiko; Kanazaki, Takuro Chemistry Letters, 1989 , p. 137 - 140

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Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

~%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

~%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

~%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

~%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

~%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

~%

Temocapril Structure

Temocapril

CAS#:111902-57-9

Literature: Chemistry Letters, , p. 137 - 140

 Synonyms

2-[(2S)-6-[[(2S)-1-ethoxy-1-oxo-4-phenyl-butan-2-yl]amino]-5-oxo-2-thiophen-2-yl-1,4-thiazepan-4-yl]ethanoic acid
2-[(2S)-6-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-5-oxo-2-thiophen-2-yl-1,4-thiazepan-4-yl]acetic acid
TemocaprilnDiscontinued
2-[(2S)-6-[[(1S)-1-carbethoxy-3-phenyl-propyl]amino]-5-keto-2-(2-thienyl)-1,4-thiazepan-4-yl]acetic acid
TEMOCAPRIL
2-((2S,6R)-6-((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-ylamino)-5-oxo-2-(thiophen-2-yl)-1,4-thiazepan-4-yl)aceticacid
Temocapil
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