Cefotiam

Chemical compound
  • J01DC07 (WHO)
Legal statusLegal status
  • In general: ℞ (Prescription only)
Pharmacokinetic dataBioavailability60% (intramuscular)Protein binding40%MetabolismNilElimination half-lifeApproximately 1 hourExcretionRenalIdentifiers
  • (6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)acetyl]
    amino}-3-{[1-(2-dimethylaminoethyl)tetrazol-5-yl]
    sulfanylmethyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]
    oct-2-ene-2-carboxylic acid
CAS Number
  • 61622-34-2 checkY
PubChem CID
  • 43708
DrugBank
  • DB00229 checkY
ChemSpider
  • 39831 checkY
UNII
  • 91W6Z2N718
KEGG
  • D07648 checkY
ChEBI
  • CHEBI:355510 checkY
ChEMBL
  • ChEMBL1296 checkY
CompTox Dashboard (EPA)
  • DTXSID6022763 Edit this at Wikidata
ECHA InfoCard100.205.922 Edit this at WikidataChemical and physical dataFormulaC18H23N9O4S3Molar mass525.62 g·mol−13D model (JSmol)
  • Interactive image
  • CN(C)CCN1N=NN=C1SCC1=C(N2[C@H](SC1)[C@H](NC(=O)CC1=CSC(N)=N1)C2=O)C(O)=O
  • InChI=1S/C18H23N9O4S3/c1-25(2)3-4-26-18(22-23-24-26)34-7-9-6-32-15-12(14(29)27(15)13(9)16(30)31)21-11(28)5-10-8-33-17(19)20-10/h8,12,15H,3-7H2,1-2H3,(H2,19,20)(H,21,28)(H,30,31)/t12-,15-/m1/s1 checkY
  • Key:QYQDKDWGWDOFFU-IUODEOHRSA-N checkY
  (verify)

Cefotiam is a parenteral third-generation cephalosporin antibiotic. It has broad-spectrum activity against Gram-positive and Gram-negative bacteria. As a beta-lactam, its bactericidal activity results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins.

It was patented in 1973 and approved for medical use in 1981.[1]

Medical uses

This drug is indicated for prophylaxis for surgical infection, postoperative infections, bacterial septicaemia, bone and joint infections, cholangitis, cholecystitis, peritonitis, prostatitis, pyelonephritis, respiratory tract infections, skin and soft tissue infections, cystitis, urethritis, and infections caused by susceptible organisms. It does not have activity against Pseudomonas aeruginosa.[citation needed]

Dosage

For adults, the dose is up to 6 grams daily by intravenous or intramuscular route in divided doses according to severity of infection. In patients with renal impairment a dose reduction may be needed.[citation needed]

Spectrum of bacterial susceptibility

Cefotiam has a broad spectrum of activity and has been used to treat infections caused by a number of enteric bacteria and bacteria responsible for causing skin infections. The following represents MIC susceptibility data for a few medically significant bacteria.

  • Bacteroides fragilis: - 16 - >128 μg/ml
  • Clostridium difficile: >128 μg/ml
  • Staphylococcus aureus: 0.25 - 32 μg/ml

[2]

Adverse effects

Side effects include nausea and vomiting, diarrhoea, hypersensitivity reactions, nephrotoxicity, convulsions, CNS toxicity, hepatic dysfunction, haematologic disorders, pain at injection site, thrombophlebitis, pseudomembranous colitis, and superinfection with prolonged use.[citation needed]

Mechanism of action

Cefotiam inhibits final cross-linking stage of peptidoglycan production, thus inhibiting bacterial cell wall synthesis. It has similar or less activity against Gram-positive staphylococci and streptococci, but is resistant to some beta-lactamases produced by Gram-negative bacteria. It is more active against many of the Enterobacteriaceae including Enterobacter, E. coli, Klebsiella, Salmonella and indole-positive Proteus species.[citation needed]

In clinical use, high concentrations of cefotiam are observed in several tissues (kidney, heart, ear, prostate, and genital tract), as well as in fluids and secretions (bile, ascitic fluid).[citation needed]

References

  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 978-3-527-60749-5.
  2. ^ "Cefotiam hydrochloride" (PDF). Susceptibilty and Resistance Data. TOKU-E. 24 February 2014. Archived from the original (PDF) on 2016-03-04. Retrieved 2014-02-06.

Further reading

  • Müller R, Böttger C, Wichmann G (2003). "Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients". Arzneimittel-Forschung. 53 (2): 126–132. doi:10.1055/s-0031-1297083. PMID 12642969. S2CID 38768846.
  • Kolben M, Mandoki E, Ulm K, Freitag K (January 2001). "Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section". European Journal of Clinical Microbiology & Infectious Diseases. 20 (1): 40–42. doi:10.1007/s100960000365. PMID 11245321. S2CID 26877334.
  • Shimizu S, Chen KR, Miyakawa S (1996). "Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses". Dermatology. 192 (2): 174–176. doi:10.1159/000246352. PMID 8829507.
  • v
  • t
  • e
Beta-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Glycopeptides
Lipoglycopeptides
Lipopeptides
Polymyxins
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin§
Intracellular
Other