110221-44-8

Basic information

• Product Name: Temocapril hydrochloride
• Synonyms: TEMOCAPRIL HYDROCHLORIDE;Temocapril Hcl;TemocarpileHCL;Temocarpilhydrochloride;(2S,6R)-6-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]tetrahydro-5-oxo-2-(2-thienyl)-1,4-thiazepine-4(5H)-acetic Acid Hydrochloride;Acecol;CS-622;1,4-Thiazepine-4(5H)-acetic acid, 6-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]tetrahydro-5-oxo-2-(2-thienyl)-, monohydrochloride, (2S,6R)- (9CI)
• CAS NO: 110221-44-8
• Molecular Formula: C₂₃H₂₈N₂O₅S₂*ClH
• Molecular Weight: 513.076
• EINECS: 1312995-182-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 110221-44-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 196-2000C (dec)
• Boiling Point: 717.4 °C at 760 mmHg
• Flash Point: 387.7 °C
• Appearance: white solid powder
• Density: 1.33g/cm³
• Vapor Pressure: 1.34E-21mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: -20°C Freezer
• Solubility: DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Temocapril hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Temocapril hydrochloride(110221-44-8)
• EPA Substance Registry System: Temocapril hydrochloride(110221-44-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 110221-44-8(Hazardous Substances Data)

Usage

Description

Temocapril hydrochloride, marketed under the brand name Acecol, is a novel angiotensin-converting enzyme (ACE) inhibitor used for the treatment of hypertension. It is three times more potent than enalapril by oral administration and has a long duration of action. Temocapril is characterized by a rapid onset of action due to its fast conversion to the active diacid metabolite. Unlike most ACE inhibitors, which are excreted mainly through the kidneys, temocapril is excreted predominantly through the biliary route, making it especially useful for treating hypertensive patients with renal dysfunction. Additionally, its potential usefulness in the treatment of congestive heart failure has been reported. Temocapril hydrochloride is a white to off-white solid.

Uses

Used in Pharmaceutical Industry:
Temocapril hydrochloride is used as an angiotensin-converting enzyme (ACE) inhibitor for the treatment of hypertension. It is effective in lowering blood pressure and has a long duration of action, making it a suitable choice for patients with hypertension.
Used in Renal Dysfunction Treatment:
Temocapril hydrochloride is used as a hypertensive treatment for patients with renal dysfunction. Its predominant biliary excretion route makes it especially useful for patients with compromised kidney function, as it reduces the burden on the kidneys.
Used in Congestive Heart Failure Treatment:
Temocapril hydrochloride has been reported to have potential usefulness in the treatment of congestive heart failure. As an ACE inhibitor, it can help manage the symptoms and progression of this condition.

Originator

Sankyo (Japan)

InChI:InChI=1/C23H28N2O5S2/c1-2-30-23(29)17(11-10-16-7-4-3-5-8-16)24-18-15-32-20(19-9-6-12-31-19)13-25(22(18)28)14-21(26)27/h3-9,12,17-18,20,24H,2,10-11,13-15H2,1H3,(H,26,27)/t17-,18-,20-/m0/s1

Upstream product

• 110143-57-2 (S)-2-((2S,6R)-5-Oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 
• 110221-26-6 (2S,6R)-6-Amino-2-thiophen-2-yl-[1,4]thiazepan-5-one 
• 102090-86-8 N-t-butoxycarbonyl-S-[2-nitro-1-(thien-2-yl)ethyl]-L-cysteine 
• 102090-87-9 S-[2-amino-1-(thien-2-yl)ethyl]-N-t-butoxycarbonyl-L-cysteine 
• 950913-92-5 6(R)-t-butoxycarbonylamino-5-oxo-2-(2-thienyl)perhydro-1,4-thiazepine 
• 110143-65-2 2-oxo-4-phenylbut-3-enoic acid 2-isopropyl-5-methylcyclohexyl ester 
• 88767-98-0 ethyl (R)-4-phenyl-2-<<(trifluoromethyl)sulfonyl>oxy>butyrate 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 29678-81-7 (R)-2-hydroxy4-phenylbutanoic acid 
• 110143-66-3 R-2-hydroxy-4-phenylbutyric acid L-menthyl ester 
• 1914-59-6 (E)-2-oxo-4-phenyl-3-butenoic acid 
• 34312-77-1 1-(2-thienyl)-2-nitroethene 
• 110221-37-9 (S)-2-((2S,6R)-4-tert-Butoxycarbonylmethyl-5-oxo-2-thiophen-2-yl-[1,4]thiazepan-6-ylamino)-4-phenyl-butyric acid ethyl ester 

Downstream Products

• 1448222-97-6 (S)-temocapril sulfoxide hydrochloride 
• 1448222-98-7 (R)-temocapril sulfoxide hydrochloride 
• 110221-53-9 [3H]-Temocaprilat 

Relevant articles and documents

Angiotensin-Converting Enzyme Inhibitors: Perhydro-1,4-thiazepin-5-one Derivatives

α-amino>-5-oxoperhydro-1,4-thiazepin-4-yl>acetic acids (monoester monoacids) and their dicarboxylic acids having the hydrophobic substituents at the 2- or 3-position of the thiazepinone ring were prepared and assayed for angiotensin-converting enzyme (ACE) inhibitory activity.The dicarboxylic acids having the pseudoequatorial amino groups at the 6-position and the pseudoequatorial hydrophobic substituents at the 2- or 3-position of the chair conformation of the thiazepinone ring had potent in vitro inhibitory activity.The monoester monoacids having the hydrophobic substituents at the 2-position suppressed pressor response to angiotensin I for a longer duration than those having the substituents at the 3-position when administered orally.The structure-activity relationship was studied by conformational energy calculations of the thiazepinone ring.