Latamoxef

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Latamoxef
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Intramuscular, intravenous
ATC code
Pharmacokinetic data
Protein binding35 to 50%
MetabolismNil
Elimination half-life2 hours
ExcretionMostly renal, unchanged; also biliary
Identifiers
  • (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
JSmol)
Melting point117 to 122 °C (243 to 252 °F) (dec.)
  • 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 checkY
  • Key:JWCSIUVGFCSJCK-CAVRMKNVSA-N checkY
 ☒NcheckY (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 a disulfiram 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]

Synthesis

Oxa-substituted third generation cephalosporin antibiotic (oxacephalosporin).

Moxalactam synthesis:[4][5][6][7][8] (excerpt from Lednicer book 3)

The

PCl5 and then to the imino methyl ether (with methanol) and next hydrolyzed to the free amine (8). Imine formation with 3,5-di-t-butyl-4-hydroxybenzaldehyde is next carried out leading to 9. Oxidation with nickel(III) oxide gives iminoquinone methide 10, to which methanol is added in a conjugate sense and in the sterechemistry represented by formula 11. The imine is exchanged with Girard's reagent T to give 12, and this is acylated by a suitable protected arylmalonate, as the hemiester hemiacid chloride so as to give 11. Deblocking with aluminium chloride
and anisole gives moxalactam 14.

References

  1. PMID 6217353
    .
  2. PMID 3778044
    .
  3. PMID 3296254
    .
  4. ^ DE 2713370, Nagata W, Narisada M, "1-Oxadethiacephalosporine, Verfahren zu Arzneimittel [1-oxadethiacephalosporins, procedure for medicinal products]", published 1977-09-29, assigned to Shionogi & Co. Ltd. 
  5. ^ US 4138486, Nagata W, Narisada M, issued 1979, assigned to Shionogi 
  6. PMID 448673
    .
  7. S2CID 45623930
    .
  8. doi:10.3987/S-1977-02-0839 (inactive 2024-02-07).{{cite journal}}: CS1 maint: DOI inactive as of February 2024 (link
    )
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