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Details

Stereochemistry ACHIRAL
Molecular Formula C20H18F2N4O3.ClH
Molecular Weight 436.84
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Fandofloxacin hydrochloride

SMILES

Cl.CN1CCN(CC1)C2=CC3=C(C=C2F)C(=O)C(=CN3C4=NC=C(F)C=C4)C(O)=O

InChI

InChIKey=UPCHGBDAUCFDMW-UHFFFAOYSA-N
InChI=1S/C20H18F2N4O3.ClH/c1-24-4-6-25(7-5-24)17-9-16-13(8-15(17)22)19(27)14(20(28)29)11-26(16)18-3-2-12(21)10-23-18;/h2-3,8-11H,4-7H2,1H3,(H,28,29);1H

HIDE SMILES / InChI
Molecular Formula C20H18F2N4O3
Molecular Weight 400.3787
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Fandofloxacin is a difluoroquinolone derivative. This compound possesses an antibacterial spectrum comparable to those of rufloxacin and ciprofloxacin in vivo. Fandofloxacin showed a rapid and nearly complete absorption, and a long residence time in the body. Because it has been reported that the in vivo antibacterial activity of Fandofloxacin is comparable or superior to other quinolones, despite the fact that its in vitro activity is significantly lower than that of the other compounds, the pharmacokinetics of this antibiotic may be responsible, at least in part, for the enhanced in vivo antibacterial activity of Fandofloxacin. Fandofloxacin is an inhibitor of bacterial DNA gyrase. The toxicities and adverse effects of Fandofloxacin observed in various toxicology studies and clinical trials were less than those of commercially available drugs. It has been in phase II clinical trial for the treatment of Urinary tract infections. However, this research has been discontinued in 2008.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase II
1132
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.36 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
8 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.47 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
5.65 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
107.4 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
114.8 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
82.2 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
87.7 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
17.15 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
16.74 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
18.34 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
17.54 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
50%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
400 mg 1 times / day steady-state, oral
dose: 400 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
50%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
50%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9786475
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FANDOFLOXACIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L435P
BOC Sciences
164150-99-6
https://www.bocsci.com/fandofloxacin-cas-164150-99-6-item-65165.html
PubMed

PubMed

TitleDatePubMed
Pharmacokinetic study of a new quinolone, DW-116.
1995
In-vitro and in-vivo activities of DW-116, a new fluoroquinolone.
1997 Apr
Pharmacokinetics of 1-(5-fluoro-2-pyridyl)-6-fluoro-7-(4-methyl-1- piperazinyl)-1,4-dihydro-4-oxoquinolone-3-carboxylic acid hydrochloride (DW-116), a new quinolone antibiotic in rats.
1997 May
Developmental toxicity assessment of the new fluoroquinolone antibacterial DW-116 in rabbits.
2005 Jan-Feb
Patents

Patents

CA2395459A1
2
CA2628178A1
6
JP2758722B2
2
US5496947
2

Sample Use Guides

In Vivo Use Guide
400 mg tablet once daily
Route of Administration: Oral
In Vitro Use Guide
Against S.pyogenes, Fandofloxacin (DW-116) (MIC50=2 mg/L; MIC90=4 mg/L) was two- or four-fold more active than rufloxacin (MIC50=8 mg/L; MIC90=8 mg/L) and it exhibited similar activity to sparfloxacin, ciprofloxacin and ofloxacin. DW-116 (MIC50=4–8 mg/L; MIC90=8–32 mg/L) was more active than rufloxacin (MIC50=4–16 mg/L; MIC90=16–32 mg/L) and less active than sparfloxacin and ciprofloxacin against S. pneumoniae and Enterococcus faecalis. Antibacterial activity of DW-116 against E. coli (MIC range 0.25–32 mg/L) was slightly inferior to that of sparfloxacin (MIC range 0.03–4 mg/L), ciprofloxacin (MIC range < 0.008–1 mg/L) and ofloxacin (MIC range 0.015–16 mg/L) and similar to that of rufloxacin (MIC range 0.25–32 mg/L).
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:40:55 UTC 2023
Edited
by admin
on Sat Dec 16 09:40:55 UTC 2023
Record UNII
7E8D75M2X3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Fandofloxacin hydrochloride
Common Name English
DW116
Code English
6-Fluoro-1-(5-fluoropyridin-2-yl)-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride
Systematic Name English
DW-116
Code English
3-Quinolinecarboxylic acid, 6-fluoro-1-(5-fluoro-2-pyridinyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-, monohydrochloride
Systematic Name English
3-Quinolinecarboxylic acid, 6-fluoro-1-(5-fluoro-2-pyridinyl)-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxo-, hydrochloride (1:1)
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID1043918
Created by admin on Sat Dec 16 09:40:56 UTC 2023 , Edited by admin on Sat Dec 16 09:40:56 UTC 2023
PRIMARY
PUBCHEM
178086
Created by admin on Sat Dec 16 09:40:56 UTC 2023 , Edited by admin on Sat Dec 16 09:40:56 UTC 2023
PRIMARY
CAS
164150-85-0
Created by admin on Sat Dec 16 09:40:56 UTC 2023 , Edited by admin on Sat Dec 16 09:40:56 UTC 2023
PRIMARY
FDA UNII
7E8D75M2X3
Created by admin on Sat Dec 16 09:40:56 UTC 2023 , Edited by admin on Sat Dec 16 09:40:56 UTC 2023
PRIMARY
Related Record Type Details
Structure of FANDOFLOXACIN
PARENT -> SALT/SOLVATE
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