Cefalotin

Cefalotin (INN) /ˌsɛfəˈloʊtɪn/ or cephalothin (USAN) /ˌsɛfəˈloʊθɪn/ is a first-generation cephalosporin antibiotic with broad spectrum antibiotic activity.^[1][2] It was the first cephalosporin marketed (1964) and continues to be widely used.^[3] 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.^[2]

Cefalotin

Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682860
Pregnancy category	AU: A
Routes of administration	Intravenous
ATC code	J01DB03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Bioavailability	n/a
Protein binding	65 to 80%
Metabolism	Hepatic
Elimination half-life	30 minutes to 1 hour
Excretion	Renal
Identifiers
IUPAC name (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	153-61-7 Y
PubChem CID	6024
DrugBank	DB00456 Y
ChemSpider	5802 Y
UNII	R72LW146E6
KEGG	D07635 Y
ChEBI	CHEBI:124991 Y
ChEMBL	ChEMBL617 Y
CompTox Dashboard (EPA)	DTXSID4022783
ECHA InfoCard	100.005.288
Chemical and physical data
Formula	C16H16N2O6S2
Molar mass	396.43 g·mol−1
3D model (JSmol)	Interactive image
Melting point	160 to 160.5 °C (320.0 to 320.9 °F)
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=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 Y Key:XIURVHNZVLADCM-IUODEOHRSA-N Y
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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.^[4]

The compound is a derivative of thiophene-2-acetic acid.^[5]