Enalaprilat dihydrateProduct ingredient for Enalaprilat
- Name
- Enalaprilat dihydrate
- Drug Entry
- Enalaprilat
Enalaprilat is the active metabolite of the orally available pro-drug, enalapril. Used in the treatment of hypertension, enalapril is an ACE inhibitor that prevents Angiotensin Converting Enzyme (ACE) from transforming angiotensin I into angiotensin II. As angiotensin II is responsible for vasoconstriction and sodium reabsorption in the proximal tubule of the kidney, down-regulation of this protein results in reduced blood pressure and blood fluid volume. Enalaprilat was originally created to overcome the limitations of the first ACE inhibitor, captopril, which had numerous side effects and left a metallic taste in the mouth. Removal of the problematic thiol group from captopril resulted in enalaprilat, which was then modified further with an ester to create the orally available pro-drug enalapril.
Enalaprilat is poorly orally available and is therefore only available as an intravenous injection for the treatment of hypertension when oral therapy is not possible.
- Accession Number
- DBSALT002434
- Structure
- Synonyms
- Enalapril diacid dihydrate / Enalprilat hydrate / Enalprilate hydrate
- External IDs
- MK-422
- UNII
- GV0O7ES0R3
- CAS Number
- 84680-54-6
- Weight
- Average: 384.429
Monoisotopic: 384.18965125 - Chemical Formula
- C18H28N2O7
- InChI Key
- MZYVOFLIPYDBGD-MLZQUWKJSA-N
- InChI
- InChI=1S/C18H24N2O5.2H2O/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13;;/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25);2*1H2/t12-,14-,15-;;/m0../s1
- IUPAC Name
- (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid dihydrate
- SMILES
- O.O.C[C@H](N[C@@H](CCC1=CC=CC=C1)C(O)=O)C(=O)N1CCC[C@H]1C(O)=O
- External Links
- KEGG Drug
- D03769
- ChemSpider
- 5292946
- ChEBI
- 59877
- ChEMBL
- CHEMBL3989406
- Predicted Properties
Property Value Source Water Solubility 0.876 mg/mL ALOGPS logP -0.09 ALOGPS logP -1.1 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 3.13 Chemaxon pKa (Strongest Basic) 7.83 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 106.94 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 90.06 m3·mol-1 Chemaxon Polarizability 36.4 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon