Cefonicid

Cefonicid
Clinical data
AHFS/Drugs	Micromedex Detailed Consumer Information
MedlinePlus	a601206
ATC code	J01DC06(WHO);
Identifiers
	IUPAC name (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	61270-58-4;
PubChemCID	43594;
ChemSpider	39734;
UNII	6532B86WFG;
KEGG	D07644;
ChEBI	CHEBI:3491;
ChEMBL	ChEMBL1601;
CompTox Dashboard(EPA)	DTXSID7022758;
Chemical and physical data
Formula	C18H18N6O8S3
Molar mass	542.56g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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; Key:DYAIAHUQIPBDIP-AXAPSJFSSA-N;
	(verify)

Cefonicide(orcefonicid) is acephalosporin antibiotic.^[1]

It has a density of 1.92g/cm³.

Synthesis

Injectable semi-synthetic cephalosporin antibiotic related tocefamandole,q.v.

Cefonicid is synthesized conveniently by nucleophilic displacement of the 3-acetoxy moiety of1with the appropriately substituted tetrazole thiole2.The mandelic acid amide C-7 side chain is reminiscent ofcefamandole.

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 toSmithKline Corp.
^D. A. Berges,U.S. patent 4,048,311(1977 toSmith Kline).
^U.S. patent 4,093,723,U.S. patent 4,159,373(1978, 1979 both toSmith Kline).

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[1] 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.

[2] DE 2611270,Berges, David Alan, "Cephalosporin-Derivate [Cephalosporin derivatives]", published 1976-09-30, assigned toSmithKline Corp.

[3] D. A. Berges,U.S. patent 4,048,311(1977 toSmith Kline).

[4] U.S. patent 4,093,723,U.S. patent 4,159,373(1978, 1979 both toSmith Kline).

[1]

[2]

[3]

[4]

Synthesis

See also

References