(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; (2Z)-but-2-enedioic acid

• ChemBase ID: 72825
• Molecular Formular: C24H32N2O9
• Molecular Mass: 492.51888
• Monoisotopic Mass: 492.21078061
• SMILES: c1cccc(c1)CC[C@H](N[C@H](C(=O)N1[C@@H](CCC1)C(=O)O)C)C(=O)OCC.C(=O)(O)/C=C\C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CCOC(=O)[C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C20H28N2O5.C4H4O4/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25;5-3(6)1-2-4(7)8/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,16-,17-;/m0./s1
• InChIKey: OYFJQPXVCSSHAI-QFPUQLAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; (2Z)-but-2-enedioic acid
• IUPAC Traditional name: enalapril; maleic acid; @enalapril; maleic acid
• Synonyms: N-[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline (2Z)-2-Butenedioate; Acapril; Acetensil; Alphrin; Amprace; Enaloc; Enapren; Enapril; Enaprin; Hipoartel; Hytrol; Innovace; Innovade; Lapril; Lotrial; MK 421; Reniten; Renivace; Tenace; Unaril; Xanef; (S,S,S)-Enalapril Maleate; Vasotec; Glioten; Renitec; Enalapril maleate

Database IDs

• CAS Number: 76095-16-4
• PubChem SID: 162037746
• PubChem CID: 5388961

CALCULATED PROPERTIES

• Acid pKa: 3.6713305
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.29928052
• LogD (pH = 7.4): -1.0552722
• Log P: 0.5877766
• Molar Refractivity: 99.5746 cm^3
• Polarizability: 39.423725 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 143-144.5°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: maleate

DETAILS

Selleck Chemicals - S1941

Research Area: Cardiovascular Disease
Biological Activity:
Enalapril maleate (Vasotec), the active metabolite of enalapril, competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion. Enalaprilat may also act on kininase II, an enzyme identical to ACE that degrades the vasodilator bradykinin. [1]

Toronto Research Chemicals - E555250

An antihypertensive. An angiotensin-converting enzyme (ACE) inhibitor.

REFERENCES

• http://www.drugbank.ca/drugs/DB00584
• Gross, M., et al.: J. Pharmacol. Exp. Ther., 216, 552 (1980)
• Gomez, H.J., et al.: J. Cardiovasc. Pharmacol., 15, Suppl. 3, S26-S29, (1980)
• MacFadyen, J., et al.: Clin. Pharmacokinet., 25, 274 (1980)
• Malini, P.L.: Adv. Ther., 10, 253 (1980)