1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine
alacepril
CAS: 74258-86-9
Molecular Formula: C20H26N2O5S
1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine - Names and Identifiers
| Name | alacepril |
| Synonyms | du1219 cetapril alacepril ALACEPRIL Alacepril (s)-l-phenylalanin 1-[3-(acetylsulfanyl)-2-methylpropanoyl]prolylphenylalanine phenylalanine, 1-[3-(acetylthio)-2-methyl-1-oxopropyl]prolyl- 1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine 1-[(2S)-3-(acetylsulfanyl)-2-methylpropanoyl]-L-prolyl-L-phenylalanine L-Phenylalanine, 1-[(2S)-3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl- L-Phenylalanine, N-[1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-prolyl]-, (S)- 2-[[1-(3-Acetylsulfanyl-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid |
| CAS | 74258-86-9 |
| 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 |
1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine - Physico-chemical Properties
| Molecular Formula | C20H26N2O5S |
| Molar Mass | 406.5 |
| Density | 1.281g/cm3 |
| Melting Point | 155-156° |
| Boling Point | 679.1°C at 760 mmHg |
| Specific Rotation(α) | D25 -81.3° (c = 1.02 in ethanol) |
| Flash Point | 364.5°C |
| Vapor Presure | 2.26E-19mmHg at 25°C |
| Storage Condition | 2-8°C |
| Refractive Index | 1.581 |
| Physical and Chemical Properties | Crystallized from ethanol-n-hexane, melting point 155-156 ℃. White crystal or crystalline powder, no smell or slight peculiar smell, slightly bitter taste. Easily soluble in chloroform or methanol, more soluble in ethanol, more difficult to dissolve in acetone, less soluble in water, extremely difficult to dissolve in ether. [α]D25-81.3 (C = 1.02, ethanol). Acute toxic LD50 rats, mice (mg/kg):>5000,>5000 oral;>3000,>3000 subcutaneous injection; About 2000, about 3000 intraperitoneal injection. |
1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine - Risk and Safety
| Toxicity | LD50 in rats, mice (mg/kg): >5000, >5000 orally; >3000, >3000 s.c.; ~2000, ~3000 i.p. (Iida, pp 7033-40) |
1-(d-3-acetylthio-2-methylpropanoyl)-l-prolyl-l-phenylalanine - Reference Information
| drug interaction | alapril can be combined with hydrochlorothiazide or furosemide in the treatment of hypertension. In the treatment of heart failure, it can be combined with digitalis and potassium excretion diuretics to play a synergistic role |
| indications | alapril is clinically used for the treatment of hypertension, myocardial ischemia and heart failure. Used for hypertension: The antihypertensive effect is obvious. It can be used as the first choice and as a substitute for other drugs when the effect is not good. used for myocardial ischemia: it can not only reduce myocardial oxygen consumption, but also increase myocardial oxygen supply; it can reduce the severity and frequency of angina pectoris, and can also improve exercise tolerance, especially suitable for heart with hypertension |
| Chemical properties | Crystallized from ethanol-n-hexane, melting point 155-156 ℃. White crystal or crystalline powder, no smell or slight peculiar smell, slightly bitter taste. Easily soluble in chloroform or methanol, more soluble in ethanol, more difficult to dissolve in acetone, less soluble in water, extremely difficult to dissolve in ether. [α]D25-81.3 (C = 1.02, ethanol). Acute toxic LD50 rats, mice (mg/kg):>5000,>5000 oral;>3000,>3000 subcutaneous injection; About 2000, about 3000 intraperitoneal injection. |
| use | angiotensin converting enzyme inhibitor is a prodrug that is converted to deacetylalapril and captopril after oral administration. For primary and renal hypertension. |
| production method | 1.0g compound (I) is dissolved in dichloromethane containing N-methylmorpholine, 0.57g compound (II) is added, and the reaction is 1h to obtain compound (III). 2.5g compound (Ⅲ) was reacted in trifluoroacetic acid-anisole for 1h to obtain 1.8g arapril. |
Last Update：2024-04-09 15:16:38
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