Fleroxacin

Names

[ Name ]:
Fleroxacin

[Synonym ]:
Fleroxacin
6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-4-oxo-7-(4-methyl-1-piperazinyl)-quinoline-3-carboxylic acid
MEGALONE
6,8-difluoro-1-(2-fluoro-ethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid
6,8-Difluoro-1-(2-fluoroethyl)-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid
ro23-6240/000
3-Quinolinecarboxylic acid, 6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-
Megalocin
AM-833
Quinodis
3-quinolinecarboxylicacid,1,4-dihydro-6,8-difluoro-1-(2-fluoroethyl)-7-(4-met
hyl-1-piperazinyl)-4-oxo
MFCD00864880
6,8-difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
6,8-Difluoro-1-(2-fluoroethyl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
6,8-difluoro-1-(2-fluoroethyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid
RO-23-6240

Biological Activity

[Description]:

Fleroxacin is a broad-spectrum antimicrobial fluoroquinolone.Target: AntibacterialFleroxacin (Ro 23-6240; AM-833) is a new trifluorinated quinolone exhibiting high activity against a broad spectrum of gram-negative and gram-positive bacteria. Fleroxacin is characterized pharmacokinetically by a long elimination half-life (9 to 10 h) and high concentrations in plasma (e.g., maximum concentration of 2.3 micrograms/ml after an oral dose of 200 mg) [1]. Fleroxacin is effective against Haemophilus ducreyi in vitro. Fleroxacin, 200 or 400 mg as a single oral dose, is efficacious therapy for microbiologically proven chancroid in patients who do not have concurrent HIV-1 infection. Among HIV-1-infected men, a single dose of 200 or 400 mg of fleroxacin is inadequate therapy for chancroid [2, 3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Weidekamm, E., et al., Single- and multiple-dose pharmacokinetics of fleroxacin, a trifluorinated quinolone, in humans. Antimicrob Agents Chemother, 1987. 31(12): p. 1909-14.

[2]. MacDonald, K.S., et al., Evaluation of fleroxacin (RO 23-6240) as single-oral-dose therapy of culture-proven chancroid in Nairobi, Kenya. Antimicrob Agents Chemother, 1989. 33(5): p. 612-4.

[3]. Rubinstein, E., History of quinolones and their side effects. Chemotherapy, 2001. 47 Suppl 3: p. 3-8; discussion 44-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
535.3±50.0 °C at 760 mmHg

[ Melting Point ]:
264-266°C

[ Molecular Formula ]:
C₁₇H₁₈F₃N₃O₃

[ Molecular Weight ]:
369.338

[ Flash Point ]:
277.6±30.1 °C

[ Exact Mass ]:
369.130035

[ PSA ]:
65.78000

[ LogP ]:
1.72

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VB1999050

CHEMICAL NAME :: 3-Quinolinecarboxylic acid, 1,4-dihydro-6,8-difluoro-1-(2-fluoroethyl)-7-(4-methy l-1- piperazinyl)-4-oxo-

CAS REGISTRY NUMBER :: 79660-72-3

LAST UPDATED :: 199612

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C17-H18-F3-N3-O3

MOLECULAR WEIGHT :: 369.38

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 20405 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 21730 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Musculoskeletal - joints

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 109 gm/kg/13W-I

TOXIC EFFECTS :: Musculoskeletal - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 4550 mg/kg/13W-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Musculoskeletal - joints Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 26 gm/kg

SEX/DURATION :: male 61 day(s) pre-mating female 2 week(s) pre-mating - 7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1300 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - abortion Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :: DNA damage

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 400 ng/disk

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 38(Suppl 2),252,1990

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
VB1999050

[ HS Code ]:
2933990090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain.

Bioorg. Med. Chem. 17 , 6983-92, (2009)

Computational modeling continues to play an important role in novel therapeutics discovery and development. In this study, we have investigated the use of in silico approaches to develop inhibitors of...

QSAR-based permeability model for drug-like compounds.

Bioorg. Med. Chem. 19 , 2615-24, (2011)

A QSAR model was developed for predicting intestinal drug permeability, one of the most important parameters when evaluating compounds in drug discovery projects. First, a set of relevant properties f...

Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.

Drug Metab. Dispos. 36 , 1385-405, (2008)

We present herein a compilation and trend analysis of human i.v. pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic ...