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

CO[C@]1(NC(=O)CSC(F)F)[C@H]2OCC(CSC3=NN=NN3CCO)=C(N2C1=O)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 8504
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3430712	Inhibitor 8504
Salmonella sp. 2 Target ID: CHEMBL612618 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3430712	Inhibitor 8504
Haemophilus influenzae 10 Target ID: CHEMBL355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3430712	Inhibitor 8504
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D07963 \| https://www.ncbi.nlm.nih.gov/pubmed/9841767	Inhibitor 8504

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 8583	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 207 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33753	Curative	Approved 8583	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 50 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33753	Curative	Approved 8583	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.

C_max

Value	Dose	Analyte	Population
38.9 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31822449/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
76.6 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31822449/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
33.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
36 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
17.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
10 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: HEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
53.1 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31822449/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
111.9 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31822449/	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
616.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
611.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
387 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
15.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: HEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
15.03 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
13.63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
16.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	5 mg/kg single, intravenous dose: 5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
0.66 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8371488/	10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FLOMOXEF serum	Homo sapiens population: HEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% EXPERIMENT https://www.jstage.jst.go.jp/article/chemotherapy1953/35/Supplement1/35_Supplement1_161/_article/-char/en			FLOMOXEF serum	Homo sapiens

Doses

Dose	Population	Adverse events
1 g 2 times / day steady-state, intravenous Studied dose Dose: 1 g, 2 times / day Route: intravenous Route: steady-state Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/	Other AEs: urticaria, Hemoglobin decreased... Other AEs: urticaria (1 pt) Hemoglobin decreased (1 pt) leukocytes decreased (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/

AEs

AE	Significance	Dose	Population
Hemoglobin decreased	1 pt	1 g 2 times / day steady-state, intravenous Studied dose Dose: 1 g, 2 times / day Route: intravenous Route: steady-state Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/
leukocytes decreased	1 pt	1 g 2 times / day steady-state, intravenous Studied dose Dose: 1 g, 2 times / day Route: intravenous Route: steady-state Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/
urticaria	1 pt	1 g 2 times / day steady-state, intravenous Studied dose Dose: 1 g, 2 times / day Route: intravenous Route: steady-state Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3444025/

PubMed

Title	Date	PubMed
Cervical discitis associated with spinal epidural abscess caused by methicillin-resistant staphylococcus aureus.	1996-01	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 [MI]

Preferred Name

English

FLOMOXEF

Official Name

English

Flomoxef [WHO-DD]

Common Name

English

flomoxef [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357