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Details

Stereochemistry UNKNOWN
Molecular Formula C11H10FNO2S
Molecular Weight 239.266
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLOSEQUINAN

SMILES

CN1C=C([S+](C)[O-])C(=O)C2=CC=C(F)C=C12

InChI

InChIKey=UYGONJYYUKVHDD-UHFFFAOYSA-N
InChI=1S/C11H10FNO2S/c1-13-6-10(16(2)15)11(14)8-4-3-7(12)5-9(8)13/h3-6H,1-2H3

HIDE SMILES / InChI
Molecular Formula C11H10FNO2S
Molecular Weight 239.266
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL23.pdf

Flosequinan is a vasodilator developed for the treatment of heart failure. The drug was marketed under the name Manoplax, however it was withdrawn by the FDA decision since it increased congestive heart failure symptoms. The exact mechanism of flosequinan action is unknown, but there are studies reporting the inhibition of PDE3 activity.

Approval Year

1992
115
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 4.3 null [pIC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
MANOPLAX

Approved Use

The treatment of heart failure.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.63 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3905414
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLOSEQUINOXAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.19 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3905414
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLOSEQUINAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
160.9 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3905414
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLOSEQUINOXAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.44 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3905414
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLOSEQUINAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
37.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3905414
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLOSEQUINOXAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3905414
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLOSEQUINAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
100 mg single, intravenous
Recommended
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1884731/
unhealthy, 42 - 70 years
n = 10
Health Status: unhealthy
Condition: severe heart failure
Age Group: 42 - 70 years
Sex: M+F
Population Size: 10
Sources:
https://pubmed.ncbi.nlm.nih.gov/1884731/
Sources:
https://pubmed.ncbi.nlm.nih.gov/1884731/
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
unhealthy, 43 years
n = 9
Health Status: unhealthy
Condition: compromised hepatic function
Age Group: 43 years
Sex: M+F
Population Size: 9
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
Disc. AE: Faint, Gastrointestinal bleeding...
Other AEs: Headache...
AEs leading to
discontinuation/dose reduction:
Faint (1 patient)
Gastrointestinal bleeding (1 patient)
Other AEs:
Headache (3 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2668206/
unhealthy, adult
n = 18
Health Status: unhealthy
Condition: severe heart failure after myocardial infarction
Age Group: adult
Sex: unknown
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/2668206/
Disc. AE: Proarrhythmic effect...
AEs leading to
discontinuation/dose reduction:
Proarrhythmic effect (8 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2668206/
AEs

AEs

AESignificanceDosePopulation
Faint 1 patient
Disc. AE
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
unhealthy, 43 years
n = 9
Health Status: unhealthy
Condition: compromised hepatic function
Age Group: 43 years
Sex: M+F
Population Size: 9
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
Gastrointestinal bleeding 1 patient
Disc. AE
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
unhealthy, 43 years
n = 9
Health Status: unhealthy
Condition: compromised hepatic function
Age Group: 43 years
Sex: M+F
Population Size: 9
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
Headache 3 patients
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
unhealthy, 43 years
n = 9
Health Status: unhealthy
Condition: compromised hepatic function
Age Group: 43 years
Sex: M+F
Population Size: 9
Sources:
https://pubmed.ncbi.nlm.nih.gov/8207686/
Proarrhythmic effect 8 patients
Disc. AE
100 mg single, oral
Recommended
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/2668206/
unhealthy, adult
n = 18
Health Status: unhealthy
Condition: severe heart failure after myocardial infarction
Age Group: adult
Sex: unknown
Population Size: 18
Sources:
https://pubmed.ncbi.nlm.nih.gov/2668206/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP3A
191
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A
191
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY570875
https://www.001chemical.com/chem/76568-02-0
3B Scientific (Wuhan) Corp
3B2-1388
http://www.3bsc.com/index/pro_info.php?id=55104
AHH Chemical co.,ltd
MT-51803
http://www.ahhchemical.com/product/MT-51803.html
Ambinter
Amb21926574
http://www.ambinter.com/reference/21926574
BLD Pharm
BD655801
http://www.bldpharm.com/products/154504-94-6.html
BLD Pharm
BD130433
http://www.bldpharm.com/products/76568-02-0.html
CSNpharm
CSN11021
https://www.csnpharm.com/products/flosequinan.html
Chemspace
CSSB00009998474
https://chem-space.com/CSSB00009998474
Debye Scientific
DB-056084
http://www.debyesci.com/cas_76568-02-0.html
Finetech
FT-0630845
http://www.finetechnology-ind.com/prod/detail/pub/76568-02-0.html
Glentham Life Sciences
GP4613
http://www.glentham.com/products/product/GP4613/
Molcore
MC570875
https://www.molcore.com/product/76568-02-0
Smolecule
S528089
http://www.smolecule.com/products/s528089
THE BioTek
bt-268197
https://www.thebiotek.com/product/inhibitors/bt-268197
eNovation Chemicals
D671471
https://www.enovationchem.com/ProductDetails.asp?ProductID=D671471
PubMed

PubMed

TitleDatePubMed
A preliminary study of the effects of flosequinan on psychomotor function in healthy volunteers.
1991 Winter
Patents

Patents

04302460
6
05011931
1
05079264
1
06689791
1
06730790
1
06861528
1
07041677
1
JP2005503995A
19

Sample Use Guides

In Vivo Use Guide
Flosequinan is administered at the average dose of 84 mg given as infusion at rate 2.03 mg/min.
Route of Administration: Intravenous
In Vitro Use Guide
The contraction of guinea-pig ventricle strips was studied using 5*10(-6)-10(-4) M of flosequinan.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:15:54 UTC 2023
Edited
by admin
on Sat Dec 16 17:15:54 UTC 2023
Record UNII
6NB119DLU7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLOSEQUINAN
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
FLOSEQUINAN [MART.]
Common Name English
FLOSEQUINAN [VANDF]
Common Name English
FLOSEQUINAN [USAN]
Common Name English
4(1H)-QUINOLINONE, 7-FLUORO-1-METHYL-3-(METHYLSULFINYL)-
Systematic Name English
flosequinan [INN]
Common Name English
BTS-49-465
Code English
BTS-49465
Code English
FLOSEQUINAN [JAN]
Common Name English
Flosequinan [WHO-DD]
Common Name English
7-FLUORO-1-METHYL-3-METHYLSULFINYL-4-QUINOLONE
Systematic Name English
FLOSEQUINAN [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01DB01
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
WHO-ATC C01DB01
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
NCI_THESAURUS C29707
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
Code System Code Type Description
PUBCHEM
4474062
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
FDA UNII
6NB119DLU7
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID1048833
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
NCI_THESAURUS
C73109
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
USAN
AA-80
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
EVMPD
SUB07654MIG
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
DRUG CENTRAL
1182
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
DRUG BANK
DB13228
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
ChEMBL
CHEMBL1908307
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
MESH
C047316
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
INN
5867
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
WIKIPEDIA
FLOSEQUINAN
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
RXCUI
25089
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY RxNorm
SMS_ID
100000081019
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
CAS
76568-02-0
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY
MERCK INDEX
m5412
Created by admin on Sat Dec 16 17:15:54 UTC 2023 , Edited by admin on Sat Dec 16 17:15:54 UTC 2023
PRIMARY Merck Index
Related Record Type Details
Structure of INOSITOL 1,4,5-TRISPHOSPHATE
TARGET->INHIBITOR OF RELEASE
Appears to inhibit IP3 formation and release of Calcium.
Related Record Type Details
Structure of Flosequinoxan
METABOLITE ACTIVE -> PARENT
MAJOR
Related Record Type Details
Structure of FLOSEQUINAN
ACTIVE MOIETY
NIH
NCATS
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