FLOSEQUINAN

First approved in 1992

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1324061
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 The drug was marketed under the name Manoplax, however it was withdrawn by the FDA decision since it increased congestive heart failure symptoms.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

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 3 60 Target ID: CHEMBL2094125 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1324061	Inhibitor 8297		4.3 null [pIC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart failure 103 Sources: http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL23.pdf	Primary		Withdrawn	MANOPLAX Approved Use The treatment of heart failure.

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP3A 191

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A 191	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/9193873/	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Positive inotropy contributes to the hemodynamic mechanism of action of flosequinan (BTS 49465) in the intact dog.	1990 Jun	1694912

Patents

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 GMT 2023` Edited by `admin` on `Sat Dec 16 17:15:54 GMT 2023`
Record UNII	6NB119DLU7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLOSEQUINAN

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