POSSIBILITIES TO ACYLATE 7-AMINOCEPHALOSPORANIC ACID TO OBTAIN SOME CEPHALOSPORINS
Keywords:
7-AMINOCEPHALOSPORANIC ACID, CEFOTAXIME, CEPHALO-SPORINS, ACYLA-TION.Abstract
Aim: Acylation of 7-aminocephalosporanic acid with an adequate acyl chloride in order to obtain cefotaxime sodium salt. Material and methods: Cefotaxime sodium salt was synthesized by acylating 7-amino cephalosporanic acid with 2-[2`-chloracetamidothiazole-4-yl]-2-(syn)-methoxy-imino acetic chloride in four steps. The melting point was determined, and IR spectral analysis and elemental analysis were performed to confirm cefotaxime structure. The quantitative determination was performed. Results: The reaction conditions were established. The yield of the synthesis phases (73-80%) and actual yield (45-47%) were very good. The structure of the obtained cefotaxime sodium salt was confirmed by the IR spectral analysis and by elemental analysis (C, H, N). The melting point was 1630C. The purity of the synthesized cefotaxime sodium salt was 98.9%. Conclusions: Cefotaxime sodium salt was synthesized by acylation of 7-aminocephalosporanic acid with 2-[2`-chloracetamidothiazole-4-yl]-2-(syn)-methoxy-imino acetic chloride, in aqueous solution, then transformed into sodium salt with sodium 2-ethylhexanoate. The method proved to be very good, yields were good, it is reproducible and simple, and does not involve high risks, so it is also safe.
References
2. Cristea AN. Tratat de farmacologie. Bucureşti: Editura Medicală, 2012.
3. Tippa DMR, Singh N. Synthesis of cefotaxime from DAMA (diethyl thiophosphoryl [(z)-(2-aminothiazol-4-yl)-2-(methoxyimino) and 7-ACA (7-amino cephalosporinic acid). IJPSR 2011; 2(8): 2178-2182.
4. Diaconu E. Tendinţe şi strategii în cercetarea, fabricarea şi utilizarea penicilinelor şi cefalosporinelor. In: Nechifor M, Diaconu E editors. Actualităţi în chimioterapia antibacteriană. Iaşi: Editura Timpul, 1999, 13-56.
5. Bucourt R, Bormann D, Heymes R, Perronnet M. Chemistry of cefotaxime. J. Antimicrob. Chemother 1980; 6(A): 63-67.
6. Isogai T. New processes for production of 7-aminocefalosporanic acid from cephalosporin. In: Strohl WR editor. Biotechnology of antibiotics. 2nd edition. Boca Raton: Taylor&Francis Group, 1997, 733-751.
7. *** Farmacopeea Română. Ediţia a X-a. Bucureşti: Editura Medicală, 1993.
8. *** European Pharmacopoeia. 7.0 edition, on line, 2011.
Additional Files
Published
Issue
Section
License
COPYRIGHT
Once an article is accepted for publication, MSJ requests a transfer of copyrights for published articles.
COPYRIGHT TRANSFER FORM FOR
REVISTA MEDICO-CHIRURGICALĂ A SOCIETĂȚII DE MEDICI ȘI NATURALIȘTI DIN IAȘI /
THE MEDICAL-SURGICAL JOURNAL OF THE SOCIETY OF PHYSICIANS AND NATURALISTS FROM IASI
We, the undersigned authors of the manuscript entitled
_____________________________________________________________________________________
_____________________________________________________________________________________
warrant that this manuscript, which is submitted for publication in the REVISTA MEDICO-CHIRURGICALĂ, has not been published and it is not under consideration for publication in another journal.
- we give the consent for publication in the REVISTA MEDICO-CHIRURGICALĂ, in printed and electronic format and we transfer unconditioned and complete the copyright of this manuscript to the REVISTA MEDICO-CHIRURGICALĂ, in the event of its acceptance.
- the manuscript does not break the intellectual property rights of any other person.
- we have read the submitted version of the manuscript and we are fully responsible for the content.
Names and signatures of authors / copyright owners (the following sequence is the authorship of the article):
- ______________________________/_________________________
- ______________________________/_________________________
- ______________________________/_________________________
N.B. All the authors must sign this form