Cefonicid
Chemical compound
- J01DC06 (WHO)
- (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetyl)amino]-8-oxo-
3-{[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl}-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 61270-58-4
- 43594
- 39734 Y
- 6532B86WFG
- D07644 Y
- CHEBI:3491 Y
- ChEMBL1601 Y
- DTXSID7022758
- Interactive image
- O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4CS(=O)(=O)O)C(=O)O
InChI
- InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1 Y
- Key:DYAIAHUQIPBDIP-AXAPSJFSSA-N Y
Cefonicide (or cefonicid) is a cephalosporin antibiotic.[1]
It has a density of 1.92g/cm3.
Synthesis
Injectable semi-synthetic cephalosporin antibiotic related to cefamandole, q.v.
Cefonicid is synthesized conveniently by nucleophilic displacement of the 3-acetoxy moiety of 1 with the appropriately substituted tetrazole thiole 2. The mandelic acid amide C-7 side chain is reminiscent of cefamandole.
See also
References
- ^ Saltiel E, Brogden RN (September 1986). "Cefonicid. A review of its antibacterial activity, pharmacological properties and therapeutic use". Drugs. 32 (3): 222–59. doi:10.2165/00003495-198632030-00002. PMID 3530703. S2CID 243051006.
- ^ DE 2611270, Berges, David Alan, "Cephalosporin-Derivate [Cephalosporin derivatives]", published 1976-09-30, assigned to SmithKline Corp.
- ^ D. A. Berges, U.S. patent 4,048,311 (1977 to Smith Kline).
- ^ U.S. patent 4,093,723, U.S. patent 4,159,373 (1978, 1979 both to Smith Kline).
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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- ‡Withdrawn from market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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