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Chemical compound
Cefonicid
AHFS /
Drugs.com
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MedlinePlus
a601206
ATC code
(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
CAS Number
PubChem
CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
Formula C 18 H 18 N 6 O 8 S 3
Molar mass 542.56 g·mol−1 3D model (
JSmol )
O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4CS(=O)(=O)O)C(=O)O
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
(verify)
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 synthesis:
[2]
[3]
[4]
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 ).