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 |
- 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=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 Y
Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N Y
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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.[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 [edit]
- ^ 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.
- ^ 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.
- ^ 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.
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