Cefalotin

Cefalotin (INN) /ˌsɛfəˈloʊtɪn/ or cephalothin (USAN) /ˌsɛfəˈloʊθɪn/ is a first-generation cephalosporin antibiotic.[1] It was the first cephalosporin marketed (1964) and continues to be widely used.[2] It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agent cefalexin. Cefalotin sodium is marketed as Keflin (Lilly) and under other trade names.[3]

Cefalotin
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682860
Pregnancy
category
  • AU: A
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
Pharmacokinetic data
Bioavailabilityn/a
Protein binding65 to 80%
MetabolismHepatic
Elimination half-life30 minutes to 1 hour
ExcretionRenal
Identifiers
  • (6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.288
Chemical and physical data
FormulaC16H16N2O6S2
Molar mass396.43 g·mol−1
3D model (JSmol)
Melting point160 to 160.5 °C (320.0 to 320.9 °F)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)Cc3sccc3)COC(=O)C)C(=O)O
  • InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1 checkY
  • Key:XIURVHNZVLADCM-IUODEOHRSA-N checkY
  (verify)

The compound is a derivative of thiophene-2-acetic acid.[4]

References
  1. Hameed TK, Robinson JL (July 2002). "Review of the use of cephalosporins in children with anaphylactic reactions from penicillins". The Canadian Journal of Infectious Diseases. 13 (4): 253–8. doi:10.1155/2002/712594. PMC 2094874. PMID 18159398.
  2. Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.
  3. International Drug Names: Cefalotin
  4. Swanston, Jonathan (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..
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