SMX

(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid


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Chemical Component Summary

Name(6R,7R)-7-{[(2R)-2-hydroxy-2-phenylacetyl]amino}-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SynonymsCEFAMANDOLE, free form
Identifiers(6R,7R)-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-7-[(2-oxidanyl-2-phenyl-ethanoyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
FormulaC18 H18 N6 O5 S2
Molecular Weight462.503
TypeNON-POLYMER
Isomeric SMILESCn1c(nnn1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)C(c4ccccc4)O)SC2)C(=O)O
InChIInChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
InChIKeyOLVCFLKTBJRLHI-AXAPSJFSSA-N

Chemical Details

Formal Charge0
Atom Count49
Chiral Atom Count3
Bond Count52
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB01326 
NameCefamandole
Groups
  • experimental
  • approved
DescriptionCefamandole is also known as cephamandole. It is a parenterally administered broad-spectrum cephalosporin antibiotic. It is generally formulated as a formate ester, [cefamandole nafate]. It is no longer marketed in the United States.
Synonyms
  • (6R,7R)-7-(R)-Mandelamido-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-carboxylic acid
  • Cefadole
  • Cefamandole
  • Cephamandole
  • Céfamandole
IndicationFor the treatment of serious infections caused by susceptible strains of microorganisms.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-CodeJ01DC03
CAS number34444-01-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 2MAKDYVLEKRKYVIGGVALAIVLIYLLRLFSLQIATDDYKKNADSNAFLN...unknowninhibitor
Solute carrier family 22 member 6MAFNDLLQQVGGVGRFQQIQVTLVVLPLLLMASHNTLQNFTAAIPTHHCR...unknowninhibitor
Solute carrier family 22 member 8MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...unknowninhibitor
Solute carrier family 22 member 11MAFSKLLEQAGGVGLFQTLQVLTFILPCLMIPSQMLLENFSAAIPGHRCW...unknowninhibitor
Solute carrier family 22 member 7MGFEELLEQVGGFGPFQLRNVALLALPRVLLPLHFLLPIFLAAVPAHRCA...unknowninhibitor
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 CHEMBL1146
PubChem 456255
ChEMBL CHEMBL1146
ChEBI CHEBI:3480