Latamoxef

Latamoxef
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.  ?
Legal status  ?
Routes Intramuscular, intravenous
Pharmacokinetic data
Protein binding 35 to 50%
Metabolism Nil
Half-life 2 hours
Excretion Mostly renal, unchanged; also biliary
Identifiers
CAS number 64952-97-2 Y
ATC code J01DD06
PubChem CID 47499
DrugBank DB04570
ChemSpider 43215 Y
UNII VUF6C936Z3 Y
KEGG D08109 Y
ChEBI CHEBI:599928 N
ChEMBL CHEMBL74632 Y
Chemical data
Formula C20H20N6O9S 
Mol. mass 520.474 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

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.[1][2] Latamoxef is no longer available in the United States. As with other cephalosporins with a methylthiotetrazole side chain, latamoxef causes an antabuse 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.[3]

References

  1. ^ Weitekamp MR, Aber RC (1983). "Prolonged bleeding times and bleeding diathesis associated with moxalactam administration". JAMA 249 (1): 69–71. doi:10.1001/jama.249.1.69. PMID 6217353. 
  2. ^ Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M (1986). "Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients". Arch Intern Med 146 (11): 2159–64. doi:10.1001/archinte.146.11.2159. PMID 3778044. 
  3. ^ Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (June 1987). "The hematologic effects of latamoxef sodium when used as a prophylaxis during surgical treatment". Surg Gynecol Obstet 164 (6): 525–9. PMID 3296254. 
Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)
Glycopeptide
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin
β-lactams/
(inhibit PBP
cross-links)
Combinations
Other

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)