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Cefalotin

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Chemical compound Pharmaceutical compound
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
IUPAC name
  • (6R,7R)-3--8-oxo-7--5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.288 Edit this at Wikidata
Chemical and physical data
FormulaC16H16N2O6S2
Molar mass396.43 g·mol
3D model (JSmol)
Melting point160 to 160.5 °C (320.0 to 320.9 °F)
SMILES
  • O=C2N1/C(=C(\CS12NC(=O)Cc3sccc3)COC(=O)C)C(=O)O
InChI
  • 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
  • Key:XIURVHNZVLADCM-IUODEOHRSA-N
  (verify)

Cefalotin (INN) /ˌsɛfəˈloʊtɪn/ or cephalothin (USAN) /ˌsɛfəˈloʊθɪn/ is a first-generation cephalosporin antibiotic with broad spectrum antibiotic activity. It was the first cephalosporin marketed (1964) and continues to be widely used. Cefalotin is used for bacterial infections of the respiratory tract, urinary tract, skin, soft tissues, bones and joints, sepsis, peritonitis, osteomyelitis, mastitis, infected wounds, and post-operational infections.

It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agents cefalexin and cefadroxil. Cefalotin sodium is marketed as Keflin (Lilly) and under other trade names.

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

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. ^ "Cefalotin - an overview | ScienceDirect Topics". www.sciencedirect.com. Retrieved 2024-01-26.
  3. Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.
  4. International Drug Names: Cefalotin
  5. Swanston, Jonathan (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 3527306730..
Antibacterials active on the cell wall and envelope (J01C-J01D)
β-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
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
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