4KO

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

Created: 2013-05-13
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 4KO
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Chemical Component Summary

Name(6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia -1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SynonymsCefmetazole
Systematic Name (OpenEye OEToolkits)(6R,7S)-7-[2-(cyanomethylsulfanyl)ethanoylamino]-7-methoxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
FormulaC15 H17 N7 O5 S3
Molecular Weight471.534
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01N#CCSCC(=O)NC3(OC)C(=O)N2C(=C(CSc1nnnn1C)CSC23)C(=O)O
SMILESCACTVS3.370CO[C]1(NC(=O)CSCC#N)[CH]2SCC(=C(N2C1=O)C(O)=O)CSc3nnnn3C
SMILESOpenEye OEToolkits1.7.6Cn1c(nnn1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
Canonical SMILESCACTVS3.370 CO[C@]1(NC(=O)CSCC#N)[C@H]2SCC(=C(N2C1=O)C(O)=O)CSc3nnnn3C
Canonical SMILESOpenEye OEToolkits1.7.6 Cn1c(nnn1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O
InChIInChI1.03 InChI=1S/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1
InChIKeyInChI1.03 SNBUBQHDYVFSQF-HIFRSBDPSA-N

Drug Info: DrugBank

DrugBank IDDB00274 
NameCefmetazole
Groups
  • approved
  • investigational
DescriptionA semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.
Synonyms
  • Cefmetazolum
  • Cefmetazole sodium
  • Cefmetazole
  • Cefmetazolo
  • (6R,7S)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
IndicationFor the treatment of infections caused by susceptible organisms.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-CodeJ01DC09
CAS number56796-20-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin binding protein 2aHSVIIPGMQKDQSIHIENLKSERGKILDRNNVELANTGTAYEIGIVPKNV...unknowninhibitor
Penicillin-binding protein 1AMKFVKYFLILAVCCILLGAGSIYGLYRYIEPQLPDVATLKDVRLQIPMQI...unknowninhibitor
Penicillin-binding protein 1BMAGNDREPIGRKGKPTRPVKQKVSRRRYEDDDDYDDYDDYEDEEPMPRKG...unknowninhibitor
Peptidoglycan synthase FtsIMKAAAKTQKPKRQEEHANFISWRFALLCGCILLALAFLLGRVAWLQVISP...unknowninhibitor
D-alanyl-D-alanine carboxypeptidase DacAMNTIFSARIMKRLALTTALCTAFISAAHADDLNIKTMIPGVPQIDAESYI...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
PubChem 42008
ChEMBL CHEMBL1201195
ChEBI CHEBI:3489