75847-73-3
Product Name:
Enalapril
Formula:
C20H28N2O5
Synonyms:
(S)-(−)-1-[N-(1-Ethoxycarbonyl-3-phenylpropyl)-L -alanyl]-L proline
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CHEMICAL AND PHYSICAL PROPERTIES
| Physical Description | Solid |
|---|---|
| Melting Point | 143-144.5 |
| Solubility | 16400 mg/L |
| LogP | 0.07 |
| Stability/Shelf Life | Stable under recommended storage conditions. /Enalapril maleate/ |
| Optical Rotation | Needles from water. MP 148-151 °C. Specific optical rotation: - 67.0 deg at 0 °C (0.1M HCl). Sparingly soluble in methanol, DMF; slightly soluble in water, isopropyl alcohol; very slightly soluble in acetone, alcodhol, hexane. Practically insoluble in acetonitrile, chlorform /Enalapril diacid dihydrate/ |
| Caco2 Permeability | -5.64 |
| Dissociation Constants | 2.92 |
| Collision Cross Section | 187.2 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Other Experimental Properties | Enalapril is commercially available as the maleate salt and differs structurally from enalaprilat by the presence of an ethoxycarbonyl group rather than a carboxy group at position 1 of L-alanyl-L-proline and by the presence of the maleate salt. These structural modifications result in increased GI absorption of enalapril compared with enalaprilat, which is poorly absorbed from the GI tract. Enalapril is structurally and pharmacologically similar to captopril but contains a disubstituted nitrogen rather than a sulfhydryl group at position 3 of 2-methyl-1- oxopropyl-L-proline. |
SAFETY INFORMATION
| Signal word | Warning |
|---|---|
| Pictogram(s) |
 Exclamation Mark Irritant GHS07  Health Hazard GHS08 |
| GHS Hazard Statements |
H317:Sensitisation, Skin H361:Reproductive toxicity |
| Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. |
COMPUTED DESCRIPTORS
| Molecular Weight | 376.4 g/mol |
|---|---|
| XLogP3 | -0.1 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 10 |
| Exact Mass | 376.19982200 g/mol |
| Monoisotopic Mass | 376.19982200 g/mol |
| Topological Polar Surface Area | 95.9 Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 519 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
PRODUCT INTRODUCTION
description
Enalapril is a dicarboxylic acid monoester that is ethyl 4-phenylbutanoate in which a hydrogen alpha to the carboxy group is substituted by the amino group of L-alanyl-L-proline (S-configuration). It has a role as a prodrug, an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, an antihypertensive agent and a geroprotector. It is a dicarboxylic acid monoester and a dipeptide. It is functionally related to an enalaprilat (anhydrous).