Cefacetrile
Chemical compound
- J01DB10 (WHO) QJ51DB10 (WHO)
- In general: ℞ (Prescription only)
- (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-
8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-
carboxylic acid
- 10206-21-0 Y
- 91562
- DB01414 Y
- 82675 Y
- FDM21QQ344
- D07629 Y
- ChEMBL2104099
- DTXSID0022779
- Interactive image
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CC#N)COC(=O)C)C(=O)O
- 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 Y
- Key:RRYMAQUWDLIUPV-BXKDBHETSA-N Y
Cefacetrile (INN, also spelled cephacetrile) is a broad-spectrum first generation cephalosporin antibiotic effective in gram-positive and gram-negative bacterial infections. It is a bacteriostatic antibiotic.[1][2] Cefacetrile is marketed under the trade names Celospor, Celtol, and Cristacef,[3] and as Vetimast for the treatment of mammary infections in lactating cows.[2]
Synthesis
It was made by reacting 7-ACA (7-aminocephalosporanic acid) with cyanoacetyl chloride in the presence of tributylamine.[citation needed]
References
- ^ "Cefacetrile Summary Report" (PDF). European Medicines Agency, Committee for Veterinary Medicinal Products. 1998. Archived from the original (PDF) on 2020-05-26. Retrieved 2012-01-25.
- ^ a b Haberfeld H, ed. (2007). Austria-Codex (in German) (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-183-8.
- ^ Horiuchi N, Oyakawa Y, Oka R, Fujiwara T (October 1980). "[Clinical evaluation of cephacetrile (Celtol) for respiratory infections (author's transl)]". The Japanese Journal of Antibiotics. 33 (10): 1145–55. PMID 7206219.
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(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Glycopeptides Lipoglycopeptides |
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Lipopeptides |
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Polymyxins |
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Other |
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- Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
- DADAL/AR inhibitors (Cycloserine)
- bactoprenol inhibitors (Bacitracin)
- Hydrolyze NAM-NAG
- Tyrothricin
- Isoniazid#
- Teixobactin
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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