Title: Cefditoren
CAS Registry Number: 104145-95-1
CAS Name: (6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[(1Z)-2-(4-methyl-5-thiazolyl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: (+)-(6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-[(Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 72-(Z)-(O-methyloxime)
Manufacturers' Codes: ME-1206
Molecular Formula: C19H18N6O5S3
Molecular Weight: 506.58
Percent Composition: C 45.05%, H 3.58%, N 16.59%, O 15.79%, S 18.99%
Literature References: Broad spectrum, third generation cephalosporin; active metabolite of orally absorbed pivaloyloxymethyl ester prodrug. Prepn: K. Atsumi et al., EP 175610; eidem, US 4839350 (1986, 1989 both to Meiji); K. Sakagami et al., J. Antibiot. 43, 1047 (1990); idem et al., Chem. Pharm. Bull. 39, 2433 (1991). In vitro and in vivo activities: A. Tamura et al., Antimicrob. Agents Chemother. 32, 1421 (1988). Extensive in vitro activity study: D. Felmingham et al., Drugs Exp. Clin. Res. 20, 127 (1994). Clinical pharmacokinetics and efficacy in pediatrics: N. Iwai et al., Jpn. J. Antibiot. 47, 181 (1994), C.A. 120, 260636e (1994).
Derivative Type: Sodium salt, sesquihydrate
Molecular Formula: C19H17N6NaO5S3.1½H2O
Molecular Weight: 537.57
Percent Composition: C 42.45%, H 3.37%, N 15.63%, Na 4.28%, O 16.37%, S 17.89%
Properties: Pale yellow crystals from water, mp 195-200° (dec). [a]D20 +121.6° (c = 0.5 in methanol).
Melting point: mp 195-200° (dec)
Optical Rotation: [a]D20 +121.6° (c = 0.5 in methanol)
Derivative Type: Pivaloyloxymethyl ester
CAS Registry Number: 117467-28-4
Additional Names: Cefditoren pivoxil
Manufacturers' Codes: ME-1207
Trademarks: Meiact (Meiji Seika)
Molecular Formula: C25H28N6O7S3
Molecular Weight: 620.72
Percent Composition: C 48.37%, H 4.55%, N 13.54%, O 18.04%, S 15.50%
Properties: Pale yellow powder, mp 127-129°. [a]D20 -48.5° (c = 0.5 in methanol).
Melting point: mp 127-129°
Optical Rotation: [a]D20 -48.5° (c = 0.5 in methanol)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins. |