Title: Faropenem
CAS Registry Number: 106560-14-9
CAS Name: (5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Additional Names: fropenem; (5R,6S,8R,2¢R)-2-(2¢-tetrahydrofuryl)-6-hydroxyethylpenem-3-carboxylate
Molecular Formula: C12H15NO5S
Molecular Weight: 285.32
Percent Composition: C 50.51%, H 5.30%, N 4.91%, O 28.04%, S 11.24%
Literature References: Orally active, b-lactamase stable, penem antibiotic. Prepn: M. Ishiguro et al., EP 199446; eidem, US 4997829 (1986, 1991 both to Suntory); eidem, J. Antibiot. 41, 1685 (1988). Pharmacokinetics: A. Tsuji et al., Drug Metab. Dispos. 18, 245 (1990). In vitro antimicrobial spectrum: J. M. Woodcock et al., J. Antimicrob. Chemother. 39, 35 (1997). b-Lactamase stability: A. Dalhoff et al., Chemotherapy (Basel) 49, 229 (2003). HPLC determn in plasma: R. V. S. Nirogi et al., Arzneim.-Forsch. 55, 762 (2005). Clinical trial in urinary tract infections: S. Arakawa et al., Nishinihon J. Urol. 56, 300 (1994); in bacterial sinusitis: R. Siegert et al., Eur. Arch. Otorhinolaryngol. 260, 186 (2003).
Derivative Type: Sodium salt
CAS Registry Number: 122547-49-3
Additional Names: Furopenem
Manufacturers' Codes: ALP-201; SUN-5555; SY-5555; WY-49605
Trademarks: Farom (Daiichi)
Molecular Formula: C12H15NNaO5S
Molecular Weight: 308.31
Percent Composition: C 46.75%, H 4.90%, N 4.54%, Na 7.46%, O 25.95%, S 10.40%
Properties: [a]D22 +60° (c = 0.10).
Optical Rotation: [a]D22 +60° (c = 0.10)
Derivative Type: Daloxate
CAS Registry Number: 141702-36-5
CAS Name: (5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester
Additional Names: faropenem medoxomil
Manufacturers' Codes: Bay-56-6854; SUN-208
Trademarks: Orapem (Replidyne)
Molecular Formula: C17H19NO8S
Molecular Weight: 397.40
Percent Composition: C 51.38%, H 4.82%, N 3.52%, O 32.21%, S 8.07%
Literature References: Prepn: H. Iwata et al., WO 9203442; eidem, US 5830889 (1992, 1998 both to Suntory).
Properties: Pale yellow crystals.
Therap-Cat: Antibacterial (antibiotics).
Keywords: Antibacterial (Antibiotics); ?Lactams; Penems. |