Misplaced Pages

Latamoxef

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

This is an old revision of this page, as edited by Beetstra (talk | contribs) at 11:41, 18 January 2011 (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: UNII ChEMBL.). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Revision as of 11:41, 18 January 2011 by Beetstra (talk | contribs) (Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: UNII ChEMBL.)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff) Pharmaceutical compound
Latamoxef
Clinical data
Routes of
administration
Intramuscular, intravenous
ATC code
Pharmacokinetic data
Protein binding35 to 50%
MetabolismNil
Elimination half-life2 hours
ExcretionMostly renal, unchanged; also biliary
Identifiers
IUPAC name
  • (6R,7R)-7-{amino}-7-methoxy-3-{methyl}-8-oxo-5-oxa-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.059.334 Edit this at Wikidata
Chemical and physical data
FormulaC20H20N6O9S
Molar mass520.474 g/mol g·mol
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(\CO12(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
  (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. 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.

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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. Salem RR, McIndoe A, Matkin JA, Lidou AC, Clarke A, Wood CB (1987). "The hematologic effects of latamoxef sodium when used as a prophylaxis during surgical treatment". Surg Gynecol Obstet. 164 (6): 525–9. PMID 3296254. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
Stub icon

This systemic antibiotic-related article is a stub. You can help Misplaced Pages by expanding it.

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
Categories: