Cefacetrile

• CAT Number: R047719
• CAS Number: 10206-21-0
• Molecular Formula: C13H13N3O6S
• Molecular Weight: 339.322
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChI: InChI=1S/C13H13N3O6S/c1-6(17)22-4-7-5-23-12-9(15-8(18)2-3-14)11(19)16(12)10(7)13(20)21/h9,12H,2,4-5H2,1H3,(H,15,18)(H,20,21)/t9-,12-/m1/s1
• InChIKey: RRYMAQUWDLIUPV-BXKDBHETSA-N
• SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC#N)SC1)C(=O)O

Cephacetrile (CAS 10206-21-0) is a broad-spectrum first-generation cephalosporin with antibiotic and antibacterial activity. Cephacetrile binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Reference

1:[Stability of sulbenicillin and cefacetrile in bile (author/'s transl)]. Yoshida M, Nonoshita Y, Saito S, Hyon U, Henmi T.Jpn J Antibiot. 1980 Apr;33(4):472-7. Japanese. PMID: 7411851
2:[In vitro and in vivo antibacterial activity of combined flucloxacillin-cefacetrile (Flunicef)]. Venturini AP, Stanzani L, Mantovani V, Mascellani G.G Ital Chemioter. 1979 Jan-Dec;26(1-2):153-8. Italian. No abstract available. PMID: 554805
3:[Serum and joint levels of cefacetrile during its administration for septic arthritis]. Blanc CH, Meyer-Brunot HG, Tosch W, Schelling JL.Schweiz Med Wochenschr. 1978 Jul 1;108(26):988-94. French. PMID: 663591
4:[A clinical study of cefacetrile in the treatment for orthopedic infections (author/'s transl)]. Oto T, Yoshida M, Ueno H, Nishikawa M, Hayashi R.Jpn J Antibiot. 1977 Jul;30(7):484-7. Japanese. No abstract available. PMID: 909136