KOV

(6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid



Chemical Component Summary

Name(6R,7R)-3-[(carbamoyloxy)methyl]-7-{[(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SynonymsCefuroxime
Identifiers(6R,7R)-3-(aminocarbonyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyimino-ethanoyl]amino]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
FormulaC16 H16 N4 O8 S
Molecular Weight424.385
TypeNON-POLYMER
Isomeric SMILESCO/N=C(/c1ccco1)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)N)C(=O)O
InChIInChI=1S/C16H16N4O8S/c1-26-19-9(8-3-2-4-27-8)12(21)18-10-13(22)20-11(15(23)24)7(5-28-16(17)25)6-29-14(10)20/h2-4,10,14H,5-6H2,1H3,(H2,17,25)(H,18,21)(H,23,24)/b19-9-/t10-,14-/m1/s1
InChIKeyJFPVXVDWJQMJEE-IZRZKJBUSA-N

Chemical Details

Formal Charge0
Atom Count45
Chiral Atom Count2
Bond Count47
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB01112 
NameCefuroxime
Groups approved
DescriptionBroad-spectrum cephalosporin antibiotic resistant to beta-lactamase. It has been proposed for infections with gram-negative and gram-positive organisms, gonorrhea, and haemophilus.
Synonyms
  • Cefuroximo
  • Cephuroxime
  • Cefuroximum
  • Cefuroxime
  • Cefuroxime axetil
Brand Names
  • Zinacef Inj 750mg/vial
  • Ceftin - Tab 500mg
  • Zinacef Inj 7.5gm/vial
  • Kefurox
  • Kefurox Inj Pws 1.5gm/add-vantage Vial
IndicationFor the treatment of many different types of bacterial infections such as bronchitis, sinusitis, tonsillitis, ear infections, skin infections, gonorrhea, and urinary tract infections.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-Code
  • S01AA27
  • J01DC02
  • J01RA03
CAS number55268-75-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 1AMTERKREHKDRKQNKNSPKNQSKVTKFLKWFFIGILLLGITAVTVVGIYV...unknowninhibitor
Solute carrier family 15 member 1MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...unknowninhibitor
Solute carrier family 15 member 2MNPFQKNESKETLFSPVSIEEVPPRPPSPPKKPSPTICGSNYPLSIAFIV...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
PubChem 5479529
ChEMBL CHEMBL1436
ChEBI CHEBI:3515