Cefalotin

Cefalotin
Names
	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;
Clinical data
WHO AWaRe
Pregnancy; category	AU: A; US: B (No risk in non-human studies); ;
Routes of; use	Intravenous
External links
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682860
Legal
Legal status	AU: S4 (Prescription only) ; UK: POM (Prescription only) ;
Pharmacokinetics
Bioavailability	n/a
Protein binding	65 to 80%
Metabolism	Liver
Elimination half-life	30 minutes to 1 hour
Excretion	Kidney
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 ; Key:XIURVHNZVLADCM-IUODEOHRSA-N ;

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]

It is in the first-generation cephalosporin family of medications.^[4]

References

↑ 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.
↑ Greenwood D (21 February 2008). Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph. OUP Oxford. pp. 128–. ISBN 978-0-19-953484-5.
↑ International Drug Names: Cefalotin
↑ Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 830. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.

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Names

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
Clinical data
WHO AWaRe
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of use	Intravenous
External links
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682860
Legal
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetics
Bioavailability	n/a
Protein binding	65 to 80%
Metabolism	Liver
Elimination half-life	30 minutes to 1 hour
Excretion	Kidney
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