Cefotiam
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Systematic (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 |
Clinical data |
Trade names |
Pansporin |
AHFS/Drugs.com |
International Drug Names |
Pregnancy cat. |
? |
Legal status |
℞ Prescription only |
Routes |
Intravenous, intramuscular |
Pharmacokinetic data |
Bioavailability |
60% (intramuscular) |
Protein binding |
40% |
Metabolism |
Nil |
Half-life |
Approximately 1 hour |
Excretion |
Renal |
Identifiers |
CAS number |
61622-34-2 |
ATC code |
J01DC07 |
PubChem |
CID 43708 |
DrugBank |
DB00229 |
ChemSpider |
39831 Y |
UNII |
91W6Z2N718 Y |
KEGG |
D07648 Y |
ChEBI |
CHEBI:355510 Y |
ChEMBL |
CHEMBL1296 Y |
Chemical data |
Formula |
C18H23N9O4S3 |
Mol. mass |
525.631 g/mol |
SMILES
- CN(C)CCN1N=NN=C1SCC1=C(N2[C@H](SC1)[C@H](NC(=O)CC1=CSC(N)=N1)C2=O)C(O)=O
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InChI
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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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Y (what is this?) (verify)
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Cefotiam is a parenteral second-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.
Cefotiam was launched as Pansporin in February 1981 by Takeda Pharmaceutical of Japan and has been available as a generic since February 1993.
Contents
- 1 Mechanism of action
- 2 Indications
- 3 Dosage
- 4 Adverse effects
- 5 See also
- 6 External links
Mechanism of action[edit]
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.
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).
Indications[edit]
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.
Dosage[edit]
Adult: Up to 6 grams daily via intravenous or intramuscular route in divided doses according to severity of infection.
In patients with renal impairment a dose reduction may be needed.
Adverse effects[edit]
Nausea, vomiting, diarrhoea, hypersensitivity reactions, nephrotoxicity, convulsions, CNS toxicity, hepatic dysfunction, haematologic disorders, pain at injection site, thrombophloebitis, Pseudomembranous colitis, superinfection with prolonged use.
See also[edit]
External links[edit]
- Müller R, Böttger C, Wichmann G (2003). "Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients.". Arzneimittelforschung 53 (2): 126–32. PMID 12642969.
- Kolben M, Mandoki E, Ulm K, Freitag K (2001). "Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section.". Eur J Clin Microbiol Infect Dis 20 (1): 40–2. doi:10.1007/s100960000365. PMID 11245321.
- Shimizu S, Chen K, Miyakawa S (1996). "Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses.". Dermatology 192 (2): 174–6. doi:10.1159/000246352. PMID 8829507.
Antibacterials: cell envelope antibiotics (J01C-J01D)
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Intracellular |
- inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
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Glycopeptide |
- inhibit PG chain elongation: Vancomycin# (Oritavancin
- Telavancin)
- Teicoplanin (Dalbavancin)
- Ramoplanin
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β-lactams/
(inhibit PBP
cross-links) |
Penicillins
(penams)
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Extended sp.
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- aminopenicillins: Amoxicillin#
- Ampicillin# (Pivampicillin
- Hetacillin
- Bacampicillin
- Metampicillin
- Talampicillin)
- Epicillin
- carboxypenicillins: Carbenicillin (Carindacillin)
- Ticarcillin
- Temocillin
- ureidopenicillins: Azlocillin
- Piperacillin
- Mezlocillin
- other: Mecillinam (Pivmecillinam)
- Sulbenicillin
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Narrow sp.
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β-lactamase sensitive
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- Benzylpenicillin (G)#: Clometocillin
- Benzathine benzylpenicillin#
- Procaine benzylpenicillin#
- Azidocillin
- Penamecillin
- Phenoxymethylpenicillin (V)#: Propicillin
- Benzathine phenoxymethylpenicillin
- Pheneticillin
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β-lactamase resistant
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- Cloxacillin# (Dicloxacillin
- Flucloxacillin)
- Oxacillin
- Meticillin
- Nafcillin
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Penems
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Carbapenems
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- Biapenem
- Ertapenem
- antipseudomonal (Doripenem
- Imipenem
- Meropenem)
- Panipenem
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Cephalosporins/Cephamycins
(cephems)
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1st (PEcK)
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- Cefazolin#
- Cefacetrile
- Cefadroxil
- Cefalexin
- Cefaloglycin
- Cefalonium
- Cefaloridine
- Cefalotin
- Cefapirin
- Cefatrizine
- Cefazedone
- Cefazaflur
- Cefradine
- Cefroxadine
- Ceftezole
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2nd (HEN)
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- Cefaclor
- Cefamandole
- Cefminox
- Cefonicid
- Ceforanide
- Cefotiam
- Cefprozil
- Cefbuperazone
- Cefuroxime
- Cefuzonam
- cephamycin (Cefoxitin
- Cefotetan
- Cefmetazole)
- carbacephem (Loracarbef)
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3rd
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- Cefixime#
- Ceftriaxone#
- antipseudomonal (Ceftazidime#
- Cefoperazone)
- Cefcapene
- Cefdaloxime
- Cefdinir
- Cefditoren
- Cefetamet
- Cefmenoxime
- Cefodizime
- Cefotaxime
- Cefpimizole
- Cefpiramide
- Cefpodoxime
- Cefsulodin
- Cefteram
- Ceftibuten
- Ceftiolene
- Ceftizoxime
- oxacephem (Flomoxef
- Latamoxef ‡)
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4th (antips-)
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- Cefepime
- Cefozopran
- Cefpirome
- Cefquinome
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5th
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- Ceftobiprole
- Ceftaroline fosamil
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Veterinary
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- Ceftiofur
- Cefquinome
- Cefovecin
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Monobactams
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- Aztreonam
- Tigemonam
- Carumonam
- Nocardicin A
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β-lactamase inh.
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- penam (Sulbactam
- Tazobactam)
- clavam (Clavulanic acid)
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Combinations
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- Amoxicillin/clavulanic acid#
- Imipenem/cilastatin#
- Ampicillin/flucloxacillin
- Ampicillin/sulbactam (Sultamicillin)
- Piperacillin/tazobactam
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Other |
- polymyxins/detergent (Colistin
- Polymyxin B)
- depolarizing (Daptomycin)
- hydrolyze NAM-NAG (Lysozyme)
- Gramicidin
- Isoniazid
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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gr+f/gr+a (t)/gr-p (c)/gr-o
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drug (J1p, w, n, m, vacc)
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