Cefotiam: Difference between revisions

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{{drugbox
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 460024199
| IUPAC_name = (6''R'',7''R'')-7-{[2-(2-amino-1,3-thiazol-4-yl)acetyl]<br>amino}-3-{[1-(2-dimethylaminoethyl)tetrazol-5-yl]<br>sulfanylmethyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]<br>oct-2-ene-2-carboxylic acid
| IUPAC_name = (6''R'',7''R'')-7-{[2-(2-amino-1,3-thiazol-4-yl)acetyl]<br>amino}-3-{[1-(2-dimethylaminoethyl)tetrazol-5-yl]<br>sulfanylmethyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]<br>oct-2-ene-2-carboxylic acid
| image = Cefotiam.svg
| image = Cefotiam.jpg
| width = 250
| width = 250
| image2 = Cefotiam.svg
<!--Clinical data-->
| tradename =  Pansporin
| Drugs.com = {{drugs.com|international|cefotiam}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  Rx-only
| routes_of_administration = [[Intravenous therapy|Intravenous]], [[intramuscular injection|intramuscular]]
<!--Pharmacokinetic data-->
| bioavailability = 60% (intramuscular)
| protein_bound = 40%
| metabolism = Nil
| elimination_half-life = Approximately 1 hour
| excretion = [[Kidney|Renal]]
<!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 61622-34-2
| CAS_number = 61622-34-2
| ATC_prefix = J01
| ATC_prefix = J01
| ATC_suffix = DC07
| ATC_suffix = DC07
| ATC_supplemental =  
| ATC_supplemental =
| PubChem = 43708
| PubChem = 43708
| DrugBank = APRD00855
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| C = 18 | H = 23 | N = 9 | O = 4 | S = 3
| DrugBank = DB00229
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 39831
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 91W6Z2N718
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07648
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 355510
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1296
 
<!--Chemical data-->
| C=18 | H=23 | N=9 | O=4 | S=3  
| molecular_weight = 525.631 g/mol
| molecular_weight = 525.631 g/mol
| bioavailability = 60% ([[intramuscular injection|intramuscular]])
| smiles = CN(C)CCN1N=NN=C1SCC1=C(N2[C@H](SC1)[C@H](NC(=O)CC1=CSC(N)=N1)C2=O)C(O)=O
| protein_bound = 40%
| 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
| metabolism = Nil
| InChIKey = QYQDKDWGWDOFFU-IUODEOHRBO
| elimination_half-life = Approximately 1 hour
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion = [[Kidney|Renal]]
| StdInChI = 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
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US = <!-- A / B / C / D / X -->
| StdInChIKey = QYQDKDWGWDOFFU-IUODEOHRSA-N
| pregnancy_category =  
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  
| routes_of_administration = [[Intravenous therapy|Intravenous]], intramuscular
}}
}}
{{SI}}


'''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.
==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 test|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).
==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
<ref>http://www.toku-e.com/Assets/MIC/Cefotiam%20hydrochloride.pdf</ref>


'''Cefotiam''' is a second-generation [[cephalosporin]] [[antibiotic]].
==Indications==
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]]''.
 
==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.
 
==Adverse effects==
Side effects include nausea and vomiting, diarrhoea, hypersensitivity reactions, [[nephrotoxicity]], convulsions, CNS toxicity, hepatic dysfunction, haematologic disorders, pain at injection site, thrombophloebitis, [[pseudomembranous colitis]], and [[superinfection]] with prolonged use.


==External links==
==External links==
* {{cite journal | author = Müller R, Böttger C, Wichmann G | title = Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. | journal = Arzneimittelforschung | volume = 53 | issue = 2 | pages = 126-32 | year = 2003 | id = PMID 12642969}}
* {{cite journal | author = Müller R, Böttger C, Wichmann G | title = Suitability of cefotiam and cefuroxime axetil for the perioperative short-term prophylaxis in tonsillectomy patients. | journal = Arzneimittelforschung | volume = 53 | issue = 2 | pages = 126–32 | year = 2003 | pmid = 12642969 | doi=10.1055/s-0031-1297083}}
* {{cite journal | author = Kolben M, Mandoki E, Ulm K, Freitag K | title = Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. | journal = Eur J Clin Microbiol Infect Dis | volume = 20 | issue = 1 | pages = 40-2 | year = 2001 | id = PMID 11245321}}
* {{cite journal | author = Kolben M, Mandoki E, Ulm K, Freitag K | title = Randomized trial of cefotiam prophylaxis in the prevention of postoperative infectious morbidity after elective cesarean section. | journal = Eur J Clin Microbiol Infect Dis | volume = 20 | issue = 1 | pages = 40–2 | year = 2001 | pmid = 11245321 | doi = 10.1007/s100960000365}}
* {{cite journal | author = Shimizu S, Chen K, Miyakawa S | title = Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. | journal = Dermatology | volume = 192 | issue = 2 | pages = 174-6 | year = 1996 | id = PMID 8829507}}
* {{cite journal | author = Shimizu S, Chen K, Miyakawa S | title = Cefotiam-induced contact urticaria syndrome: an occupational condition in Japanese nurses. | journal = Dermatology | volume = 192 | issue = 2 | pages = 174–6 | year = 1996 | pmid = 8829507 | doi = 10.1159/000246352}}
 
{{reflist|30em}}


{{CephalosporinAntiBiotics}}
{{CephalosporinAntiBiotics}}
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[[Category:Tetrazoles]]
[[Category:Tetrazoles]]
[[Category:Cephalosporin antibiotics]]
[[Category:Cephalosporin antibiotics]]
[[th:เซโฟเตียม]]
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Revision as of 18:29, 10 April 2015

Cefotiam
File:Cefotiam.svg
Clinical data
Trade namesPansporin
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intravenous, intramuscular
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60% (intramuscular)
Protein binding40%
MetabolismNil
Elimination half-lifeApproximately 1 hour
ExcretionRenal
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC18H23N9O4S3
Molar mass525.631 g/mol
3D model (JSmol)
  (verify)

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.

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.

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).

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

[1]

Indications

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.

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.

Adverse effects

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

External links

  • 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. doi:10.1055/s-0031-1297083. 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.
  1. ↑ http://www.toku-e.com/Assets/MIC/Cefotiam%20hydrochloride.pdf
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