cefotetan

Also known as ICI-156834, (6R,7S)-7-[4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido]-7-methoxy-3-{[(1-methyl-1H-tetrazol-5- yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- carboxylic acid

Cefotetan is an injectable antibiotic of the cephamycin type for prophylaxis and treatment of bacterial infections. It is often grouped together with second-generation cephalosporins and has a similar antibacterial spectrum, but with additional anti-anaerobe coverage.

Chemical data

Formula: C17H17N7O8S4
Molecular weight: 575.6 g/mol
IUPAC name: (7S)-7-[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES: CN1C(=NN=N1)SCC2=C(N3C([C@@](C3=O)(NC(=O)C4SC(=C(C(=O)N)C(=O)O)S4)OC)SC2)C(=O)O
InChIKey: SRZNHPXWXCNNDU-PGEKIEPBSA-N
XLogP: 0.1
Polar surface area: 321 Å²
H-bond donors: 4
H-bond acceptors: 15
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1985
Admin. routes: parenteral
Indications: osteomyelitis, bacterial disease, Cholecystitis

via ChEMBL · EBI

Research

864 papers

Cefotetan.2006
Cefotetan: a review of the microbiologic properties and antimicrobial spectrum.American journal of surgery · 1988
Cefotetan. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use.Drugs · 1985
Clinical pharmacokinetics of cefotetan.Clinical pharmacokinetics · 1994
Cefotetan-bound human RKIP involves in Ras/Raf1/MEK/ERK signaling pathway.Acta biochimica et biophysica Sinica · 2022

via PubMed

Wikidata facts

Subclass of: cephalosporin antibiotic
Mass: 575.0021445040001

Show 9 more facts

discoverer or inventor: Astellas Pharma
chemical formula: C₁₇H₁₇N₇O₈S₄
medical condition treated: staphylococcal infection
World Health Organisation international non-proprietary name: cefotetan
defined daily dose: 4
subject has role: antibiotic
isomeric SMILES: CO[C@]1(NC(=O)C2SC(=C(C(=O)N)C(=O)O)S2)[C@H]3SCC(=C(N3C1=O)C(=O)O)CSc4nnnn4C
stylized name: cefoTEtan
canonical SMILES: COC1(NC(=O)C2SC(=C(C(N)=O)C(=O)O)S2)C(=O)N2C(C(=O)O)=C(CSc3nnnn3C)CSC21

Sources (6)

via Wikidata · CC0

~3 min read

Encyclopedic overview

4 sections

Contents

Adverse effects
Spectrum of bacterial susceptibility
References
External links

{{Drugbox | Verifiedfields = changed | verifiedrevid = 401948686 | IUPAC_name = (7S)-7-{[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)1,3-dithietane-2-carbonyl]amino}-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | image = Cefotetan.svg | image_class = skin-invert-image | width = 250

Excerpted from Wikipedia’s “cefotetan” article, available under the CC BY-SA 4.0 licence.

Available in 19 languages

via Wikidata sitelinks · CC0