FLOMOXEF

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H18F2N6O7S2
Molecular Weight	496.466
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12OCC(CSC3=NN=NN3CCO)=C(N1C(=O)[C@]2(NC(=O)CSC(F)F)OC)C(O)=O

InChI

InChIKey=UHRBTBZOWWGKMK-DOMZBBRYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C65693
Curator's Comment: Description was created based on several sources, including http://adisinsight.springer.com/drugs/800003964 http://evanigma.zapto.org:8081/wikipedia_en_medicine_2016-01/A/Flomoxef.html http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33753

Flomoxef is a cephamycin antibiotic with a difluoromethylthio-acetamido group at the 7-beta position of the cephem nucleus, commonly used for postoperative prophylaxis. Flomoxef has activity against epidermides, streptococci, propionibacteria, and both methicillin-resistant and -susceptible Staphylococcus aureus. Flomoxef exhibits a broad spectrum of antibacterial activity against G(+), G(-) and even anaerobes such as Staphylococcus sp., Escherichia coli, and Bacteroides sp., and it can be used singly to treat infection caused by aerobes and anaerobes (Mixed infection) effectively. Flomoxef belongs to the cephamycin, so it is very stable against β-lactamase as well as Extended Spectrum β-lactamase (ESBL), a novel resistance induced by Enterobacteriaceae. There is no Oxyimino group in the structure of Flomoxef, so it won’t derive ESBL and it is also effective for the treatment to ESBL infection. No disulfiram-like reaction and less incidence of vitamin K deficiency than that of Latamoxef. Marketed in Japan as FLUMARIN.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26625536	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3430712	Inhibitor 8297
Salmonella sp. 2 Target ID: CHEMBL612618 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3430712	Inhibitor 8297
Haemophilus influenzae 10 Target ID: CHEMBL355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3430712	Inhibitor 8297
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D07963 \| https://www.ncbi.nlm.nih.gov/pubmed/9841767	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33753	Curative	Approved 8429	FLUMARIN Approved Use This medicine is an oxacephem antibiotic and has an antibacterial effect by inhibiting bacterial cell wall synthesis. It is usually used for the treatment of a wide range of bacterial infections including surgical infections, respiratory infections, urinary tract infections, intra-abdominal infections, biliary tract infections, obstetric and gynecologic infections, otorhinolaryngologic infections, etc.
Urinary tract infections 205 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33753	Curative	Approved 8429	FLUMARIN Approved Use This medicine is an oxacephem antibiotic and has an antibacterial effect by inhibiting bacterial cell wall synthesis. It is usually used for the treatment of a wide range of bacterial infections including surgical infections, respiratory infections, urinary tract infections, intra-abdominal infections, biliary tract infections, obstetric and gynecologic infections, otorhinolaryngologic infections, etc.
Intra-abdominal infections 49 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33753	Curative	Approved 8429	FLUMARIN Approved Use This medicine is an oxacephem antibiotic and has an antibacterial effect by inhibiting bacterial cell wall synthesis. It is usually used for the treatment of a wide range of bacterial infections including surgical infections, respiratory infections, urinary tract infections, intra-abdominal infections, biliary tract infections, obstetric and gynecologic infections, otorhinolaryngologic infections, etc.

PubMed

Title	Date	PubMed
Cervical discitis associated with spinal epidural abscess caused by methicillin-resistant staphylococcus aureus.	1996 Jan	8786835

Patents

Sample Use Guides

In Vivo Use Guide

The usual dose is 1 to 2 g daily in two divided doses. In general, for adults, the medicine is administered by intravenous injection or intravenous drip infusion daily in 2 divided doses. For children, it is administered by intravenous injection or intravenous drip infusion daily in 3 or 4 divided doses. For premature infants and neonates within 3 days after birth, it is administered by intravenous injection or intravenous drip infusion daily in 2 or 3 divided doses. For premature infants and neonates on the 4th day or later after birth, it is administered by intravenous injection or intravenous drip infusion daily in 3 or 4 divided doses. In case of intractable and/or severe infections, for adults, the medicine is administered by intravenous injection or intravenous drip infusion daily in 2 to 4 divided doses, and for premature infants, neonates and children, the medicine is administered by intravenous injection or intravenous drip infusion daily in 3 or 4 divided doses.

Route of Administration: Intravenous

In Vitro Use Guide

The distribution of MIC's of Flomoxef against Escherichia coli and Salmonella spp. ranged from 0.05 to 0.78 ug/ml and from 0.05 to 0.39 ug/ml, respectively.

Name

Type

Language

FLOMOXEF

Official Name

English

FLOMOXEF [MI]

Common Name

English

Flomoxef [WHO-DD]

Common Name

English

flomoxef [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357