Chemical Component Summary

NameOmapatrilat
Identifiers(4~{S},7~{S},10~{a}~{S})-5-oxidanylidene-4-[[(2~{S})-3-phenyl-2-sulfanyl-propanoyl]amino]-2,3,4,7,8,9,10,10~{a}-octahydropyrido[2,1-b][1,3]thiazepine-7-carboxylic acid
FormulaC19 H24 N2 O4 S2
Molecular Weight408.535
TypeNON-POLYMER
Isomeric SMILESc1ccc(cc1)C[C@@H](C(=O)N[C@H]2CCS[C@H]3CCC[C@H](N3C2=O)C(=O)O)S
InChIInChI=1S/C19H24N2O4S2/c22-17(15(26)11-12-5-2-1-3-6-12)20-13-9-10-27-16-8-4-7-14(19(24)25)21(16)18(13)23/h1-3,5-6,13-16,26H,4,7-11H2,(H,20,22)(H,24,25)/t13-,14-,15-,16-/m0/s1
InChIKeyLVRLSYPNFFBYCZ-VGWMRTNUSA-N

Chemical Details

Formal Charge0
Atom Count51
Chiral Atom Count4
Bond Count53
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB00886 
NameOmapatrilat
Groups investigational
DescriptionOmapatrilat is an investigational drug that inhibits both neutral endopeptidase (NEP) and angiotensin converting enzyme (ACE). The inhibition of NEP elevates natriuretic peptide levels, increasing excretion of sodium in urine, dilating blood vessels, and reducing preload and ventricular remodeling. This drug from BMS was not approved by the FDA due to angioedema safety concerns.
Synonyms
  • Omapatrilate
  • Omapatrilat
IndicationFor the treatment of hypertension.
Categories
  • Agents Acting on the Renin-Angiotensin System
  • Agents causing angioedema
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Angiotensin-Converting Enzyme Inhibitors
CAS number167305-00-2

Drug Targets

NameTarget SequencePharmacological ActionActions
NeprilysinMGKSESQMDITDINTPKPKKKQRWTPLEISLSVLVLLLTIIAVTMIALYA...unknown
Angiotensin-converting enzymeMGAASGRRGPGLLLPLPLLLLLPPQPALALDPGLQPGNFSADEAGAQLFA...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 CHEMBL289556
PubChem 656629
ChEMBL CHEMBL289556
ChEBI CHEBI:135660