Cefotiam

Cefotiam

Clinical data
Trade names	Pansporin
AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous, intramuscular
ATC code	J01DC07 ( WHO )
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	60% (intramuscular)
Protein binding	40%
Metabolism	Nil
Elimination half-life	Approximately 1 hour
Excretion	Renal
Identifiers
IUPAC name (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  Y
PubChem CID	43708
DrugBank	DB00229  Y
ChemSpider	39831  Y
UNII	91W6Z2N718
KEGG	D07648  Y
ChEBI	CHEBI:355510  Y
ChEMBL	ChEMBL1296  Y
CompTox Dashboard (EPA)	DTXSID6022763
ECHA InfoCard	100.205.922
Chemical and physical data
Formula	C18H23N9O4S3
Molar mass	525.62 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCN1N=NN=C1SCC1=C(N2[C@H](SC1)[C@H](NC(=O)CC1=CSC(N)=N1)C2=O)C(O)=O
InChI 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 Y Key:QYQDKDWGWDOFFU-IUODEOHRSA-N Y
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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 sepsis, 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 the 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 several 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
• Clostridioides 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 the 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.