EAL

1-((2S)-2-{[(1S)-1-CARBOXY-3-PHENYLPROPYL]AMINO}PROPANOYL)-L-PROLINE

Created: 2004-03-11
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count49
Chiral Atom Count3
Bond Count50
Aromatic Bond Count6
2D diagram of EAL
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Chemical Component Summary

Name1-((2S)-2-{[(1S)-1-CARBOXY-3-PHENYLPROPYL]AMINO}PROPANOYL)-L-PROLINE
SynonymsENALAPRILAT INHIBITOR
Systematic Name (OpenEye OEToolkits)(2S)-1-[(2S)-2-[[(2S)-1-hydroxy-1-oxo-4-phenyl-butan-2-yl]amino]propanoyl]pyrrolidine-2-carboxylic acid
FormulaC18 H24 N2 O5
Molecular Weight348.394
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=C(O)C2N(C(=O)C(NC(C(=O)O)CCc1ccccc1)C)CCC2
SMILESCACTVS3.341C[CH](N[CH](CCc1ccccc1)C(O)=O)C(=O)N2CCC[CH]2C(O)=O
SMILESOpenEye OEToolkits1.5.0CC(C(=O)N1CCCC1C(=O)O)NC(CCc2ccccc2)C(=O)O
Canonical SMILESCACTVS3.341 C[C@H](N[C@@H](CCc1ccccc1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O
Canonical SMILESOpenEye OEToolkits1.5.0 C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N[C@@H](CCc2ccccc2)C(=O)O
InChIInChI1.03 InChI=1S/C18H24N2O5/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)/t12-,14-,15-/m0/s1
InChIKeyInChI1.03 LZFZMUMEGBBDTC-QEJZJMRPSA-N

Drug Info: DrugBank

DrugBank IDDB09477 
NameEnalaprilat
Groups approved
DescriptionEnalaprilat 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.
Synonyms
  • Enalaprilat anhydrous
  • Enalaprilat
  • Enalaprilat dihydrate
Brand Names
  • Enalaprilat Injection USP
  • Enalaprilat
  • Vasotec IV
IndicationEnalaprilat injection is indicated for the treatment of hypertension when oral therapy is not practical.
Categories
  • Agents Acting on the Renin-Angiotensin System
  • Agents causing angioedema
  • Agents causing hyperkalemia
  • Amino Acids, Peptides, and Proteins
  • Angiotensin-Converting Enzyme Inhibitors
CAS number76420-72-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Angiotensin-converting enzymeMGAASGRRGPGLLLPLPLLLLLPPQPALALDPGLQPGNFSADEAGAQLFA...unknowninhibitor
B1 bradykinin receptorMASSWPPLELQSSNQSQLFPQNATACDNAPEAWDLLHRVLPTFIISICFF...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL577
PubChem 5462501
ChEMBL CHEMBL577
ChEBI CHEBI:4786