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74258-86-9

Basic Information
CAS No.: 74258-86-9
Name: Alacepril
Article Data: 3
Molecular Structure:
Molecular Structure of 74258-86-9 (Alacepril)
Formula: C20H26N2O5S
Molecular Weight: 406.503
Synonyms: L-Phenylalanine,N-[1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl]-, (S)-;Cetapril;DU 1219;L-Phenylalanine,1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl-;
Density: 1.281 g/cm3
Melting Point: 155-156°
Boiling Point: 679.1 °C at 760 mmHg
Flash Point: 364.5 °C
Hazard Symbols: Xn
Risk Codes: R22
PSA: 129.08000
LogP: 2.03410
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    Alacepril

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    Alacepril CAS#74258-86-9 Storage:Keep container tightly closed in a dry, cool and well-ventilated place. Package:25Kg/drum, 150Kg/drum, 200kg/drum, According to request. Transportation:By sea, by air.

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    Alacepril,74258-86-9

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Specification

1. Introduction of Alacepril
Alacepril is one kind of powder. It belongs to the product category of Active Pharmaceutical Ingredients. What's more, its IUPAC name is 2-[[1-(3-Acetylsulfanyl-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid and systematic name is called 1-[(2S)-3-(Acetylsulfanyl)-2-methylpropanoyl]-L-prolyl-L-phenylalanine. This chemical's classification codes are Angiotensin-converting Enzyme Inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Hypertensive; Protease Inhibitors and Reproductive Effect.

2. Properties of Alacepril
Physical properties about Alacepril are:
(1) ACD/LogP: 1.99; 92) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): -0.26; (4) ACD/LogD (pH 7.4): -1.62; (5) ACD/BCF (pH 5.5): 1; (6) ACD/BCF (pH 7.4): 1; (7) ACD/KOC (pH 5.5): 1.63; (8) ACD/KOC (pH 7.4): 1; (9) #H bond acceptors: 7; (10) #H bond donors: 2; (11) #Freely Rotating Bonds: 9; (12) Polar Surface Area: 109.29 Å2; (13) Index of Refraction: 1.581; (14) Molar Refractivity: 105.81 cm3; (15) Molar Volume: 317.3 cm3; (16) Surface Tension: 57.4 dyne/cm; (17) Density: 1.281 g/cm3; (18) Flash Point: 364.5 °C; (19) Enthalpy of Vaporization: 104.69 kJ/mol; (20) Boiling Point: 679.1 °C at 760 mmHg; (21) Vapour Pressure: 2.26E-19 mmHg at 25 °C.

3. Structure Descriptors of Alacepril
(1) SMILES: O=C(N[C@H](C(=O)O)Cc1ccccc1)[C@H]2N(C(=O)[C@H](C)CSC(=O)C)CCC2
(2) InChI: InChI=1/C20H26N2O5S/c1-13(12-28-14(2)23)19(25)22-10-6-9-17(22)18(24)21-16(20(26)27)11-15-7-4-3-5-8-15/h3-5,7-8,13,16-17H,6,9-12H2,1-2H3,(H,21,24)(H,26,27)/t13-,16+,17+/m1/s1
(3) InChIKey: FHHHOYXPRDYHEZ-COXVUDFIBE

4. The toxicity data of Alacepril
The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 1600mg/kg (1600mg/kg)   Drugs in Japan Vol. -, Pg. 64, 1990.
mouse LD50 intraperitoneal 2921mg/kg (2921mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 7033, 1985.
mouse LD50 intravenous > 1gm/kg (1000mg/kg)   European Patent Application. Vol. #7477,
mouse LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 7033, 1985.
mouse LD50 subcutaneous > 3gm/kg (3000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 7033, 1985.
rat LD50 intraperitoneal 1872mg/kg (1872mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 7033, 1985.
rat LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 7033, 1985.
rat LD50 subcutaneous > 3gm/kg (3000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 7033, 1985.
women TDLo oral 120mg/kg/17W- (120mg/kg) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Internal Medicine. Vol. 38, Pg. 164, 1999.
 

5. Uses of Alacepril
Alacepril is an ACE inhibitor. Alacepril can be used in the medicine which can treat hypertension; myocardial ischemia or cardiac failure.Amyl acetate can be used to manufacture Alacepril.

6. Production of Alacepril
0g compound (I) was dissolved in dichloromethane containing N-methyl morpholine was added 0.57g of compound (II), for 1h, the obtained compound (III). 2.5g of compound (III) in trifluoroacetic acid - anisole reaction 1h. Then you can get the Alacepril.

Production of Alacepril