CE3

(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxo-5-thia-1-azabicy clo[4.2.0]oct-2-ene-2-carboxylic acid

Created: 2005-12-07
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count47
Chiral Atom Count2
Bond Count49
Aromatic Bond Count5
2D diagram of CE3
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Chemical Component Summary

Name(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxo-5-thia-1-azabicy clo[4.2.0]oct-2-ene-2-carboxylic acid
SynonymsCEFOTAXIME
Systematic Name (OpenEye OEToolkits)(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-azanyl-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
FormulaC16 H17 N5 O7 S2
Molecular Weight455.465
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(O)C=2N3C(=O)C(NC(=O)C(=N\OC)/c1nc(sc1)N)C3SCC=2COC(=O)C
SMILESCACTVS3.370CON=C(C(=O)N[CH]1[CH]2SCC(=C(N2C1=O)C(O)=O)COC(C)=O)c3csc(N)n3
SMILESOpenEye OEToolkits1.7.6CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)c3csc(n3)N)SC1)C(=O)O
Canonical SMILESCACTVS3.370 CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(=C(N2C1=O)C(O)=O)COC(C)=O)c3csc(N)n3
Canonical SMILESOpenEye OEToolkits1.7.6 CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/c3csc(n3)N)SC1)C(=O)O
InChIInChI1.03 InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1
InChIKeyInChI1.03 GPRBEKHLDVQUJE-QSWIMTSFSA-N

Drug Info: DrugBank

DrugBank IDDB00493 
NameCefotaxime
Groups approved
DescriptionCefotaxime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime sodium is marketed under various trade names including Claforan (Sanofi-Aventis).
Synonyms
  • Cefotaximum
  • Cefotaxima
  • Cefotaxim
  • (6R,7R)-3-(acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cephotaxime
Brand Names
  • Claforan 1gm/vial
  • Cefotaxime Sodium Sterile
  • Claforan
  • Claforan 2gm/vial
  • Cefotaxime and Dextrose
IndicationUsed to treat gonorrhoea, meningitis, and severe infections including infections of the kidney (pyelonephritis) and urinary system. Also used before an operation to prevent infection after surgery.
Categories
  • Agents that reduce seizure threshold
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
ATC-CodeJ01DD01
CAS number63527-52-6

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 1bMQNQLNELKRKMLEFFQQKQKNKKSARPGKKGSSTKKSKTLDKSAIFPAI...unknowninhibitor
Penicillin-binding protein 2aMKLDKLFEKFLSLFKKETSELEDSDSTILRRSRSDRKKLAQVGPIRKFWR...unknowninhibitor
Penicillin-binding protein 3MLKKCILLVFLCVGLIGLIGCSKTDSPEDRMEAFVKQWNDQQFDDMYQSL...unknowninhibitor
Penicillin-binding protein 1AMNKPTILRLIKYLSISFLSLVIAAIVLGGGVFFYYVSKAPSLSESKLVAT...unknowninhibitor
Penicillin-binding protein 2BMRKFNSHSIPIRLNLLFSIVILLFMTIIGRLLYMQVLNKDFYEKKLASAS...unknowninhibitor
View More
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 CHEMBL1730
PubChem 5742673
ChEMBL CHEMBL1730
ChEBI CHEBI:204928