Cefdinir

Title: Cefdinir
CAS Registry Number: 91832-40-5
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: syn-7-[2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid
Manufacturers' Codes: FK-482; BMY-28488
Trademarks: Omnicef (Abbott)
Molecular Formula: C14H13N5O5S2
Molecular Weight: 395.41
Percent Composition: C 42.53%, H 3.31%, N 17.71%, O 20.23%, S 16.22%
Literature References: Cephalosporin antibiotic structurally similar to cefixime, q.v. Prepn: T. Takaya et al., BE 897864; eidem, US 4559334 (1984, 1985 both to Fujisawa); Y. Inamoto et al., J. Antibiot. 41, 828 (1988); H. Kamachi et al., ibid. 1602. Improved prepn: M. González et al., Farmaco 58, 409 (2003). Clinical trial in children with acute otitis media: S. L. Block et al., Pediatr. Infect. Dis. J. 23, 834 (2004). Review of pharmacokinetics and in vitro antimicrobial activity: D. R. P. Guay, ibid. 19, S141-S146 (2000); of antibacterial activity, pharmacology and clinical efficacy: C. M. Perry, L. J. Scott, Drugs 64, 1433-1464 (2004).
Properties: White to slightly brownish-yellow solid, mp 170° (dec). uv max (pH 7 phosphate buffer): 223, 286 nm (e 17400, 19700). pKa 9.70. Slightly sol in dilute HCl; sparingly sol in 0.1 M pH 7.0 phosphate buffer.
Melting point: White to slightly brownish-yellow solid, mp 170° (dec)
pKa: pKa 9.70
Absorption maximum: uv max (pH 7 phosphate buffer): 223, 286 nm (e 17400, 19700)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefditoren Cefetamet Cefixime Cefmenoxime Cefmetazole

Cefdinir
Cefdinir.svg
Systematic (IUPAC) name
8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-
ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-
azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
Clinical data
Trade names Cefzon
AHFS/Drugs.com monograph
MedlinePlus a698001
Pregnancy cat. B (US)
Legal status Rx only (US)
Routes Oral
Pharmacokinetic data
Bioavailability 16% to 21% (dose-dependent)
Protein binding 60% to 70%
Metabolism Negligible
Half-life 1.7 ± 0.6 hours
Excretion Renal
Identifiers
CAS number 91832-40-5 YesY
ATC code J01DD15
PubChem CID 6915944
DrugBank DB00535
ChemSpider 5291705 YesY
UNII CI0FAO63WC YesY
KEGG D00917 YesY
ChEBI CHEBI:3485 YesY
ChEMBL CHEMBL927 YesY
Chemical data
Formula C14H13N5O5S2 
Mol. mass 395.416 g/mol
 YesY (what is this?)  (verify)

Cefdinir is a third generation oral cephalosporin antibiotic. It was discovered by Fujisawa Pharmaceutical Co., Ltd. "Fujisawa" (now Astellas) and introduced in 1991 under the brand name Cefzon.[1][2] Warner-Lambert licensed this cephalosporin, cefdinir, for marketing in US from Fujisawa, Japan.[3] Abbott obtained U.S. marketing rights to Omnicef (Cefdinir) in December 1998 through an agreement with Warner-Lambert Company.[4] It was approved by FDA on Dec 4, 1997.[5] It is available in US as Omnicef by Abbott Laboratories and in India as Cednir by Abbott, Kefnir by Glenmark and Cefdiel by Ranbaxy.

As of 2008, cefdinir was the highest-selling cephalosporin antibiotic in the United States, with more than US$585 million in retail sales of its generic versions alone.[6]