U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C24H25NO4
Molecular Weight 391.4596
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLAVOXATE

SMILES

CC1=C(OC2=C(C=CC=C2C(=O)OCCN3CCCCC3)C1=O)C4=CC=CC=C4

InChI

InChIKey=SPIUTQOUKAMGCX-UHFFFAOYSA-N
InChI=1S/C24H25NO4/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25/h2,4-5,8-12H,3,6-7,13-16H2,1H3

HIDE SMILES / InChI
Flavoxate is a drug, indicated for symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis. Flavoxate is not indicated for definitive treatment, but is compatible with drugs used for the treatment of urinary tract infections. It was approved for use in the United States in 1970 and continues to be used. Drug acts as a direct antagonist at muscarinic acetylcholine receptors in cholinergically innervated organs. Its anticholinergic-parasympatholytic action reduces the tonus of smooth muscle in the bladder, effectively reducing the number of required voids, facilitating increased volume per void. Common side effects are those of parasympathetic stimulation and include dryness of the mouth and eyes, decreased sweating, headache, visual blurring, constipation, urinary retention, impotence, tachycardia and palpitations, anxiety, restlessness and in some instances agitation and delusions.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
FLAVOXATE HYDROCHLORIDE

Approved Use

Flavoxate HCl tablets are indicated for symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis. Flavoxate HCl tablets are not indicated for definitive treatment, but are compatible with drugs used for the treatment of urinary tract infections.

Launch Date

2004
Palliative
FLAVOXATE HYDROCHLORIDE

Approved Use

Flavoxate HCl tablets are indicated for symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis. Flavoxate HCl tablets are not indicated for definitive treatment, but are compatible with drugs used for the treatment of urinary tract infections.

Launch Date

2004
Palliative
FLAVOXATE HYDROCHLORIDE

Approved Use

Flavoxate HCl tablets are indicated for symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis. Flavoxate HCl tablets are not indicated for definitive treatment, but are compatible with drugs used for the treatment of urinary tract infections.

Launch Date

2004
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.61 mg/L
1.18 mg/kg single, intravenous
dose: 1.18 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.4 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.02 mg × h/L/(mg dose/kg)
2.55 mg/kg single, oral
dose: 2.55 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.49 mg × h/L/(mg dose/kg)
1.18 mg/kg single, intravenous
dose: 1.18 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
27.85 μg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40.1 min
1.18 mg/kg single, intravenous
dose: 1.18 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
4.06 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
3-METHYLFLAVONE-8-CARBOXYLIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
200 mg 3 times / day multiple, oral
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, 26 years
n = 1
Health Status: unhealthy
Condition: urinary infection
Age Group: 26 years
Sex: F
Population Size: 1
Sources:
Disc. AE: Erythema, Edema hands...
AEs leading to
discontinuation/dose reduction:
Erythema
Edema hands
Sources:
1200 mg 1 times / day multiple, oral
Dose: 1200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 1 times / day
Sources:
unhealthy, 49.8 ± 9.7 years
Health Status: unhealthy
Condition: unstable bladder
Age Group: 49.8 ± 9.7 years
Sex: F
Sources:
AEs

AEs

AESignificanceDosePopulation
Edema hands Disc. AE
200 mg 3 times / day multiple, oral
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, 26 years
n = 1
Health Status: unhealthy
Condition: urinary infection
Age Group: 26 years
Sex: F
Population Size: 1
Sources:
Erythema Disc. AE
200 mg 3 times / day multiple, oral
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, 26 years
n = 1
Health Status: unhealthy
Condition: urinary infection
Age Group: 26 years
Sex: F
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Development of a high-performance liquid chromatographic method for bioequivalence study of flavoxate tablets.
2001 Feb 10
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.
2002 Jan
[Alpha-blockers and bioflavonoids in men with chronic nonbacterial prostatitis (NIH-IIIa): a prospective, placebo-controlled trial].
2004 Feb
Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence.
2005 Jun
Urodynamic evaluation in primary enuresis: an investigative and treatment outcome correlation.
2007 Aug
Agents for treatment of overactive bladder: a therapeutic class review.
2007 Jul
Drug-induced acute cholestatic liver damage in a patient with mutation of UGT1A1.
2007 Jul
Anticholinergic drugs versus other medications for overactive bladder syndrome in adults.
2007 Jul 18
High performance liquid chromatographic determination of 3-methylflavone-8-carboxylic acid, the main active metabolite of flavoxate hydrochloride in human urine.
2007 May 9
Effects of flavoxate hydrochloride on voltage-dependent Ba2+ currents in human detrusor myocytes at different experimental temperatures.
2007 Nov
Anticholinergic drugs versus other medications for overactive bladder syndrome in adults.
2007 Oct 17
Persistence, adherence, and switch rates among extended-release and immediate-release overactive bladder medications in a regional managed care plan.
2008 Apr
3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid.
2008 Apr 16
The role of combination medical therapy in benign prostatic hyperplasia.
2008 Dec
[Clinical evaluation of supplemental administration of flavoxate hydrochloride in benign prostatic hyperplasia patients with nocturia resistant to an alpha1-adrenoceptor blocker].
2008 Mar
Clinical guidelines for overactive bladder.
2009 Feb
Acute myocardial infarction and Kounis syndrome.
2009 May 15
Oxybutynin extended release for the management of overactive bladder: a clinical review.
2009 Sep 21
[Urinary incontinence and puppy coat due to spaying in the bitch. An overview of pathophysiology, diagnosis and therapy].
2010 Jun 8
New insights into molecular targets for urinary incontinence.
2010 Oct
Patents

Sample Use Guides

Adults and children over 12 years of age: one or two 100 mg tablets 3 or 4 times a day. With improvement of symptoms, the dose may be reduced. This drug cannot be recommended for infants and children under 12 years of age because safety and efficacy have not been demonstrated in this age group.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The antispasmodic effects of the flavone compounds flavoxate hydrochloride on the human detrusor, prostatic adenoma, prostatic capsule, and bladder neck, were studied by the in vitro isometric method. Flavoxate showed a slightly greater activity than the other compounds in the prostatic and bladder neck tissues. The relaxant effect on the prostatic tissues suggests a potential use for these compounds in benign prostatic obstruction.
Unknown
Name Type Language
FLAVOXATE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
FLAVOXATE [MI]
Common Name English
BLADURIL
Brand Name English
Flavoxate [WHO-DD]
Common Name English
4H-1-BENZOPYRAN-8-CARBOXYLIC ACID, 3-METHYL-4-OXO-2-PHENYL-, 2-(1-PIPERIDINYL)ETHYL ESTER
Common Name English
2-PIPERIDINOETHYL 3-METHYL-4-OXO-2-PHENYL-4H-1-BENZOPYRAN-8-CARBOXYLATE
Systematic Name English
FLAVOXATE [VANDF]
Common Name English
flavoxate [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC G04BD02
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
NDF-RT N0000000125
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
NDF-RT N0000000125
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
NDF-RT N0000175700
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
WHO-VATC QG04BD02
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
NDF-RT N0000000125
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
NCI_THESAURUS C29704
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
LIVERTOX NBK548911
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
239-337-5
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PRIMARY
MERCK INDEX
m5398
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PRIMARY Merck Index
MESH
D005422
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PRIMARY
DRUG BANK
DB01148
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PRIMARY
SMS_ID
100000092354
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PRIMARY
DRUG CENTRAL
1175
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PRIMARY
EVMPD
SUB07635MIG
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PRIMARY
LACTMED
Flavoxate
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PRIMARY
INN
1929
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PRIMARY
IUPHAR
7187
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PRIMARY
RXCUI
4440
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PRIMARY RxNorm
FDA UNII
3E74Y80MEY
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PRIMARY
PUBCHEM
3354
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
CAS
15301-69-6
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
NCI_THESAURUS
C61765
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
DAILYMED
3E74Y80MEY
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
CHEBI
5088
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
WIKIPEDIA
FLAVOXATE
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID3023053
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL1493
Created by admin on Sat Dec 16 17:29:51 GMT 2023 , Edited by admin on Sat Dec 16 17:29:51 GMT 2023
PRIMARY