89396-94-1

Basic information

• Product Name: (S)-3-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-1-METHYL-2-OXO-IMIDAZOLIDINE-4-CARBOXYLIC ACID
• Synonyms: (S)-3-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-1-METHYL-2-OXO-IMIDAZOLIDINE-4-CARBOXYLIC ACID;Imidaprilhydrochloride;4-Imidazolidinecarboxylic acid, 3-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-, monohydrochloride, (4S)-;4-Imidazolidinecarboxylic acid, 3-[2-[[1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-, monohydrochloride, [4S-[3[R*(R*)],4R*]]-;Novaloc;TA 6366;Tanapril;(S)-3-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-1-METHYL-2-OXO-IMIDAZOLIDINE-4-CARBOXYLIC ACID: HYDROCHLORIDE
• CAS NO: 89396-94-1
• Molecular Formula: C₂₀H₂₇N₃O₆*ClH
• Molecular Weight: 405.44488
• EINECS: 1308068-626-2
• Product Categories: Inhibitors
• Mol File: 89396-94-1.mol
• Article Data: 2

Chemical Properties

• Melting Point: 214-216℃
• Boiling Point: 577 °C at 760 mmHg
• Flash Point: 302.8 °C
• Appearance: white to tan/
• Storage Temp.: ?20°C
• Solubility: H2O: ≥5mg/mL
• Merck: 14,4911
• CAS DataBase Reference: (S)-3-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-1-METHYL-2-OXO-IMIDAZOLIDINE-4-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-1-METHYL-2-OXO-IMIDAZOLIDINE-4-CARBOXYLIC ACID(89396-94-1)
• EPA Substance Registry System: (S)-3-[(S)-2-((S)-1-ETHOXYCARBONYL-3-PHENYL-PROPYLAMINO)-PROPIONYL]-1-METHYL-2-OXO-IMIDAZOLIDINE-4-CARBOXYLIC ACID(89396-94-1)

Safety Data

• WGK Germany: 3
• RTECS: NI8927400
• Hazardous Substances Data: 89396-94-1(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 89396-94-1 differently. You can refer to the following data:
1. Angiotensin converting enzyme (ACE) inhibitor. Antihypertensive.
2. Imidapril hydrochloride was used as a standard in bioequivalence test by LC/MS method.

General Description

Imidapril comprises large acyl moiety and is hydrolyzed by carboxylesterase (CES) 1.

Biochem/physiol Actions

Imidapril is a potent angiotensin converting enzyme inhibitor and anti-hypertensive.

Drug interactions

Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs. Antihypertensives: increased risk of hyperkalaemia, hypotension and renal failure with ARBs and aliskiren. Bee venom extract: possible severe anaphylactoid reactions when used together. Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity. Cytotoxics: increased risk of angioedema with everolimus. Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics. ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect. Gold: flushing and hypotension with sodium aurothiomalate. Lithium: reduced excretion, possibility of enhanced lithium toxicity. Potassium salts: increased risk of hyperkalaemia. Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Metabolism

Imidapril is a prodrug, and is metabolised in the liver to the diacid imidaprilat, its active metabolite. The bioavailability of imidaprilat is about 42% after oral doses of imidapril. About 40% of an oral dose is excreted in the urine, the rest in the faeces.

Upstream product

• 16503-46-1 2-bromo-4-phenyl butanoic acid 
• 83056-78-4 tert-butyl (4S)-3-(benzyloxycarbonyl)-1-methyl-2-oxoimidazolidine-4-carboxylate 
• 928142-34-1 t-butyl-(4S)-3-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylate hydrochloride 
• 89371-34-6 N-succinimidyl (2S)-2-{N-[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propionate 
• 195828-75-2 tert.-butyl (4S)-1-methyl-3-(2-bromopropionyl)-2-oxo-imidazolidine-4-carboxylate 
• 90891-21-7 L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride 
• 89371-38-0 tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate 
• 97457-39-1 Benzyl (2S)-2-amino>propionate Hydrogenmaleate 
• 83056-79-5 (4S)-1-methyl-2-oxoimidazolidine-4-carboxylic acid t-butyl ester 
• 82717-95-1 Benzyl (2S)-2-amino>propionate 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 82586-61-6 ethyl 2-bromo-4-phenylbutanoate 
• 943-73-7 D-homophenylalanine 
• 5440-40-4 2-(acetylamino)-4-phenylbutanoic acid 

Downstream Products

• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 46460-23-5 ethyl 2-amino-4-phenyl-(2S)-butyrate 
• 89371-44-8 (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid 
• 1470364-43-2 C₂₀H₂₅N₃O₅ 

Relevant articles and documents

PROCESS FOR INDUSTRIALLY VIABLE PREPARATION OF IMIDAPRIL HYDROCHLORIDE

The invention relates to a novel method for the preparation of imidapril hydrochloride of formula-l by reacting esters of 4(S)-1-methyl-2-oxoimidazolidine-4-carboxylate of formula-ll with (S)-ethyl-2-[(S)-4-methyl-2,5-dioxooxazolidin-3-yl]-4-phenylbutanoate of formula-Ill and hydrolyzing the coupled product with an alcoholic hydrochloride.