Cefixime

Title: Cefixime
CAS Registry Number: 79350-37-1
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-[2-(2-amino-4-thiazolyl)-2-(carboxymethoxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid
Manufacturers' Codes: FK-027; FR-17027; CL-284635
Trademarks: Cefixoral (Menarini); Cefspan (Fujisawa); Cephoral (Merck KGaA); Oroken (Bellon); Suprax (Wyeth); Unixime (Firma)
Molecular Formula: C16H15N5O7S2
Molecular Weight: 453.45
Percent Composition: C 42.38%, H 3.33%, N 15.44%, O 24.70%, S 14.14%
Literature References: Orally active, third generation cephalosporin antibiotic. Prepn: T. Takaya et al., EP 30630; eidem, US 4409214 (1981, 1983 both to Fujisawa); H. Yamanaka et al., J. Antibiot. 38, 1738 (1985). Synthesis and activity of (E)-isomer: K. Kawabata et al., Chem. Pharm. Bull. 34, 3458 (1986). Mechanism of action: Y. Shigi et al., J. Antibiot. 37, 790 (1984). Comparative antibacterial spectrum in vitro and in vivo: T. Kamimura et al., Antimicrob. Agents Chemother. 25, 98 (1984). In vitro activity and b-lactamase stability: H. C. Neu et al., ibid. 26, 174 (1984). HPLC determn in human plasma and urine: Y. Tokuma et al., J. Chromatogr. 311, 339 (1984). Pharmacokinetics in humans: D. R. P. Guay et al., Antimicrob. Agents Chemother. 30, 485 (1986). Clinical trial in urinary tract infections: J. Levenstein et al., S. Afr. Med. J. 70, 455 (1986); A. Irvani et al., Am. J. Med. 85, Suppl. 3A, 17 (1988); in respiratory infections: R. Kiani et al., ibid. 6.
Derivative Type: (Z)-Form disodium salt
Molecular Formula: C16H13N5Na2O7S2
Molecular Weight: 497.41
Percent Composition: C 38.63%, H 2.63%, N 14.08%, Na 9.24%, O 22.52%, S 12.89%
Properties: mp >250°.
Melting point: mp >250°
Derivative Type: (E)-Form trihydrate
Properties: Pale yellow solid, mp 218-225° (dec).
Melting point: mp 218-225° (dec)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefmenoxime Cefmetazole Cefminox Cefodizime Cefonicid

Cefixime
Cefixime.svg
Systematic (IUPAC) name
(6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxy
methoxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-
1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names Suprax
AHFS/Drugs.com monograph
MedlinePlus a690007
Pregnancy cat. B
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability 40% to 50%
Protein binding Approximately 60%
Half-life Variable
Average 3 to 4 hours
Excretion Renal and biliary
Identifiers
CAS number 79350-37-1 YesY
ATC code J01DD08
PubChem CID 5362065
DrugBank DB00671
ChemSpider 4514923 YesY
UNII 97I1C92E55 YesY
KEGG D00258 YesY
ChEBI CHEBI:472657 YesY
ChEMBL CHEMBL1541 YesY
Chemical data
Formula C16H15N5O7S2 
Mol. mass 453.452 g/mol
 YesY (what is this?)  (verify)

Cefixime (under the brand name of Suprax in the USA, Setic in Bangladesh, ) is a cephalosporin antibiotic used to treat bacterial infections.