| Revision as of 11:41, 18 January 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: UNII ChEMBL.← Previous edit | Revision as of 11:51, 18 January 2011 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[userNext edit → | ||
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| {{Drugbox | {{Drugbox | ||
| | verifiedrevid = |
| verifiedrevid = 408571626 | ||
| | IUPAC_name = (6''R'',7''R'')-7-{amino}-7-methoxy-3-{methyl}-8-oxo-5-oxa-1-azabicyclooct-2-ene-2-carboxylic acid | | IUPAC_name = (6''R'',7''R'')-7-{amino}-7-methoxy-3-{methyl}-8-oxo-5-oxa-1-azabicyclooct-2-ene-2-carboxylic acid | ||
| | image = Latamoxef.svg | | image = Latamoxef.svg | ||
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| | InChI = 1/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 | | InChI = 1/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 | ||
| | InChIKey = JWCSIUVGFCSJCK-CAVRMKNVBQ | | InChIKey = JWCSIUVGFCSJCK-CAVRMKNVBQ | ||
| | ChEMBL_Ref = {{ebicite|correct|EBI}} | |||
| | ChEMBL = 74632 | | ChEMBL = 74632 | ||
| | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ||
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| | PubChem = 47499 | | PubChem = 47499 | ||
| | DrugBank = | | DrugBank = | ||
| | KEGG_Ref = {{keggcite|correct|kegg}} | |||
| | KEGG = D08109 | | KEGG = D08109 | ||
| | smiles = O=C2N1/C(=C(\CO12(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O | | smiles = O=C2N1/C(=C(\CO12(OC)NC(=O)C(c3ccc(O)cc3)C(=O)O)CSc4nnnn4C)C(=O)O | ||
Revision as of 11:51, 18 January 2011
Pharmaceutical compound | |
| Clinical data | |
|---|---|
| Routes of administration | Intramuscular, intravenous |
| ATC code | |
| Pharmacokinetic data | |
| Protein binding | 35 to 50% |
| Metabolism | Nil |
| Elimination half-life | 2 hours |
| Excretion | Mostly renal, unchanged; also biliary |
| Identifiers | |
IUPAC name
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.059.334  |
| Chemical and physical data | |
| Formula | C20H20N6O9S |
| Molar mass | 520.474 g/mol g·mol |
| 3D model (JSmol) | |
SMILES
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InChI
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| (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
- 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.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - 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)
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