Flomoxef - Misplaced Pages

Chemical compound Pharmaceutical compound

Flomoxef
Clinical data

Trade names	Flumarin
AHFS/Drugs.com	International Drug Names
ATC code	J01DC14 (WHO)
Identifiers
IUPAC name (6R,7R)-7-amino]-3-sulfanylmethyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number	99665-00-6
PubChem CID	65864
ChemSpider	59274
UNII	V9E5U5XF42
KEGG	D07963
ChEMBL	ChEMBL15413
CompTox Dashboard (EPA)	DTXSID5048845
Chemical and physical data
Formula	C₁₅H₁₈F₂N₆O₇S₂
Molar mass	496.46 g·mol
3D model (JSmol)	Interactive image
Melting point	82.5 to 87.5 °C (180.5 to 189.5 °F)
SMILES CO1(2N(C1=O)C(=C(CO2)CSc3nnnn3CCO)C(=O)O)NC(=O)CSC(F)F
InChI InChI=1S/C15H18F2N6O7S2/c1-29-15(18-8(25)6-31-13(16)17)11(28)23-9(10(26)27)7(4-30-12(15)23)5-32-14-19-20-21-22(14)2-3-24/h12-13,24H,2-6H2,1H3,(H,18,25)(H,26,27)/t12-,15+/m1/s1 Key:UHRBTBZOWWGKMK-DOMZBBRYSA-N
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Flomoxef is an oxacephem antibiotic that was developed by Shionogi.

It has been classified either as a second-generation or fourth-generation cephalosporin.

It was patented in 1982 and approved for medical use in 1988 under the trade name Flumarin.

References

Masuda Z, Kurosaki Y, Ishino K, Yamauchi K, Sano S (April 2008). "Pharmacokinetic analysis of flomoxef in children undergoing cardiopulmonary bypass and modified ultrafiltration". General Thoracic and Cardiovascular Surgery. 56 (4): 163–169. doi:10.1007/s11748-007-0208-5. PMID 18401677. S2CID 23845740.
Ito M, Ishigami T (1991). "The meaning of the development of flomoxef and clinical experience in Japan". Infection. 19 (Suppl 5): S253–S257. doi:10.1007/bf01645536. PMID 1783441. S2CID 25339977.
Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495.

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Combinations

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

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