Latamoxef

Latamoxef
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Intramuscular, intravenous
ATC code	J01DD06 (WHO) ;
Pharmacokinetic data
Protein binding	35 to 50%
Metabolism	Nil
Elimination half-life	2 hours
Excretion	Mostly renal, unchanged; also biliary
Identifiers
	IUPAC name (6R,7R)-7-{[carboxy(4-hydroxyphenyl)acetyl]amino}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)thio]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	64952-97-2 ;
PubChem CID	47499;
DrugBank	DB04570 ;
ChemSpider	43215 ;
UNII	VUF6C936Z3;
KEGG	D08109 ;
ChEBI	CHEBI:599928 ;
ChEMBL	ChEMBL74632 ;
CompTox Dashboard (EPA)	DTXSID9023338 ;
ECHA InfoCard	100.059.334
Chemical and physical data
Formula	C20H20N6O9S
Molar mass	520.47 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	117 to 122 °C (243 to 252 °F) (dec.)
	SMILES O=C2N1/C(=C(\CO[C@@H]1[C@]2(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O;
	InChI InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1 ; Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N ;
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Latamoxef (or moxalactam) is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as latamoxef, the sulfur atom of the cephalosporin core is replaced with an oxygen atom.

Latamoxef has been associated with prolonged bleeding time, and several cases of coagulopathy, some fatal, were reported during the 1980s. Latamoxef is no longer available in the United States. As with other cephalosporins with a methylthiotetrazole side chain, latamoxef causes a disulfiram reaction when mixed with alcohol. Additionally, the methylthiotetrazole side chain inhibits γ-carboxylation of glutamic acid; this can interfere with the actions of vitamin K.

It has been described as a third-generation cephalosporin.

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