Cefonicid

Cefonicid
Names
	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;
External links
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a601206
Identifiers
CAS Number	61270-58-4;
PubChem CID	43594;
ChemSpider	39734 ;
UNII	6532B86WFG;
KEGG	D07644 ;
ChEBI	CHEBI:3491 ;
ChEMBL	ChEMBL1601 ;
ATC code	J01DC06 (WHO) ;
Chemical and physical data
Formula	C18H18N6O8S3
Molar mass	542.56 g·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 ;

Cefonicide (or cefonicid) is an antibiotic.^[1]

It is in the second-generation cephalosporin family of medications.^[2]

It has a density of 1.92g/cm³.

Synthesis

Injectable semi-synthetic cephalosporin antibiotic related to cefamandole, q.v.

Cefonicid synthesis:^[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.

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.
↑ Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 832. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.
↑ D. A. Berges, DE 2611270 ; idem, U.S. Patent 4,048,311 (1976, 1977 both 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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[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.

[Katzung2021-2] Beauduy, Camille E.; Winston, Lisa G. (2020). "43. Beta-lactam and other cell wall - & membrane - active antibiotics". In Katzung, Bertram G.; Trevor, Anthony J. (eds.). Basic and Clinical Pharmacology (15th ed.). New York: McGraw-Hill. p. 832. ISBN 978-1-260-45231-0. Archived from the original on 2021-10-10. Retrieved 2021-11-30.

[3] D. A. Berges, DE 2611270 ; idem, U.S. Patent 4,048,311 (1976, 1977 both to Smith Kline).

[4] U.S. Patent 4,093,723, U.S. Patent 4,159,373 (1978, 1979 both to Smith Kline).

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[2]

[3]

[4]

Cefonicid

Synthesis

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References

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Cefonicid

Synthesis

See also

References

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