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| Clinical data | |
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| AHFS/Drugs.com | International Drug Names |
| Routes of administration | Intramuscular,intravenous |
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| Pharmacokinetic data | |
| Protein binding | 35 to 50% |
| Metabolism | Nil |
| Eliminationhalf-life | 2 hours |
| Excretion | Mostlyrenal, unchanged; also biliary |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.059.334 |
| Chemical and physical data | |
| Formula | C20H20N6O9S |
| Molar mass | 520.47 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 117 to 122 °C (243 to 252 °F) (dec.) |
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Latamoxef (ormoxalactam) is anoxacephemantibiotic usually grouped with thecephalosporins. In oxacephems such as latamoxef, thesulfur atom of the cephalosporin core is replaced with anoxygen atom.
Latamoxef has been associated with prolongedbleeding time, and several cases ofcoagulopathy, 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 adisulfiram 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.[citation needed]
It has been described as a third-generation cephalosporin.[3]
Oxa-substituted third generation cephalosporin antibiotic (oxacephalosporin).
Thebenzhydrol ester of 6-Aminopenicillanic acid (6-APA) is S-chlorinated and treated with base whereupon the intermediatesulfenyl chloride fragments (to2). Next, displacement withpropargyl alcohol in the presence ofzinc chloride gives predominantly the stereochemistry represented by diastereoisomer3. The side chain is protected as the phenylacetylamide; the triple bond is partially reduced with a 5% Pd-CaCO3 (Lindlar catalyst) and then epoxidized withmCPBA to give4. The epoxide is opened at the least hindered end with 1-methyl-1H-tetrazole-5-thiol to put in place the future C-3 side chain and give intermediate5. Jones oxidation followed in turn by ozonolysis (reductive work-up with zinc-AcOH) and reaction withSOCl2 andpyridine give halide6. The stage is now wet for intramolecularWittig reaction. Displacement withPPh3 and Wittig olefination gives 1-oxacephem7. Next a sequence is undertaken of side chain exchange and introduction of a 7-methoxyl group analogous to that which is present incephamycins and gives them the enhancedbeta-lactamase stability. First7 is converted to the imino chloride withPCl5 and then to the imino methyl ether (withmethanol) and next hydrolyzed to the free amine (8). Imine formation with 3,5-di-t-butyl-4-hydroxybenzaldehyde is next carried out leading to9. Oxidation withnickel(III) oxide gives iminoquinone methide10, to which methanol is added in a conjugate sense and in the stereochemistry represented by formula11. The imine is exchanged withGirard's reagent T to give12, and this is acylated by a suitable protected arylmalonate, as the hemiester hemiacid chloride so as to give 11. Deblocking withaluminium chloride and anisole gives moxalactam14.