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Flomoxef

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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-[[2-(Difluoromethylsulfanyl)acetyl]amino]-3-[[1-(2-hydroxyethyl)tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	99665-00-6^Y
PubChemCID	65864
ChemSpider	59274^N
UNII	V9E5U5XF42
KEGG	D07963^Y
ChEMBL	ChEMBL15413^N
CompTox Dashboard(EPA)	DTXSID5048845
Chemical and physical data
Formula	C₁₅H₁₈F₂N₆O₇S₂
Molar mass	496.46 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	82.5 to 87.5 °C (180.5 to 189.5 °F)
SMILES CO[C@@]1([C@@H]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^N Key:UHRBTBZOWWGKMK-DOMZBBRYSA-N^N
^NY (what is this?) (verify)

Flomoxef is anoxacephem antibiotic that was developed byShionogi.

It has been classified either as a second-generation^[1] or fourth-generation cephalosporin.^[2]

It was patented in 1982 and approved for medical use in 1988 under the trade nameFlumarin.^[3]

^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

Other

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