FLAVOXATE

First approved in 1970

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 Search

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

Molecular Formula	C24H25NO4
Molecular Weight	391.4596
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a9c44c4b-5b3c-45bf-9bc9-ce858e3d06c5 | https://livertox.nlm.nih.gov/Flavoxate.htm

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptors; M1 & M2 2 Target ID: CHEMBL2095219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10858873	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
Cystitis 27 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a9c44c4b-5b3c-45bf-9bc9-ce858e3d06c5	Palliative	Approved 8583	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
Prostatitis 25 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a9c44c4b-5b3c-45bf-9bc9-ce858e3d06c5	Palliative	Approved 8583	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
Urethritis 18 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a9c44c4b-5b3c-45bf-9bc9-ce858e3d06c5	Palliative	Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
4.61 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1026965	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11232858/	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

Value	Dose	Analyte	Population
4.49 mg × h/L/(mg dose/kg) EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1026965	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
4.02 mg × h/L/(mg dose/kg) EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1026965	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
27.85 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11232858/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
40.1 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1026965	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11232858/	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

Dose	Population	Adverse 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: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348	unhealthy, 26 years Health Status: unhealthy Age Group: 26 years Sex: F Sources: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348	Disc. AE: Erythema, Edema hands... AEs leading to discontinuation/dose reduction: Erythema Edema hands Sources: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348
1200 mg 1 times / day multiple, oral Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3044876	unhealthy, 49.8 ± 9.7 years Health Status: unhealthy Age Group: 49.8 ± 9.7 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3044876	Sources: https://pubmed.ncbi.nlm.nih.gov/3044876

AEs

AE	Significance	Dose	Population
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: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348	unhealthy, 26 years Health Status: unhealthy Age Group: 26 years Sex: F Sources: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348
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: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348	unhealthy, 26 years Health Status: unhealthy Age Group: 26 years Sex: F Sources: http://www.jiaci.org/issues/vol22issue5/8-20.pdf https://pubmed.ncbi.nlm.nih.gov/10385348

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 MRP1 116 BCRP 910	CYP 303

Drug as perpetrator

Target	Modality	Activity
MRP1 232	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2711991/	weak
P-gp 1932	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2711991/	weak
BCRP 985	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2711991/	yes [IC50 20 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1906583/#B5	no

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5088	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5088
ChemicalBook	CB2341499	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2341499
eMolecules	736698	https://www.emolecules.com/cgi-bin/more?vid=736698
ZINC	ZINC000000608382	http://zinc15.docking.org/substances/ZINC000000608382

PubMed

Title	Date	PubMed
New insights into molecular targets for urinary incontinence.	2010-10	21206614
Liquid Chromatographic Determination of Flavoxate HCl in Pharmaceutical Formulation.	2010-07	21042486
Lipophilic cationic drugs increase the permeability of lysosomal membranes in a cell culture system.	2010-07	20301195
[Urinary incontinence and puppy coat due to spaying in the bitch. An overview of pathophysiology, diagnosis and therapy].	2010-06-08	22290549
Inappropriate prescribing in the hospitalized elderly patient: defining the problem, evaluation tools, and possible solutions.	2010-04-07	20396637
Oxybutynin extended release for the management of overactive bladder: a clinical review.	2009-09-21	19920931
Acute myocardial infarction and Kounis syndrome.	2009-05-15	18378025
Liquid chromatographic fingerprint of 3-methylflavone-8-carboxylic acid established for its synthesis control analysis.	2009-03-15	19159766
Polymeric matrix membrane sensors for stability-indicating potentiometric determination of oxybutynin hydrochloride and flavoxate hydrochloride urogenital system drugs.	2009-02-11	19202792
Clinical guidelines for overactive bladder.	2009-02	19228224
The role of combination medical therapy in benign prostatic hyperplasia.	2008-12	19002123
High-performance liquid chromatographic determination of flavoxate hydrochloride and its hydrolysis product.	2008-12	18850365
[Summary of the practice guideline 'Urinary incontinence' (first revision) from the Dutch College of General Practitioners].	2008-11-22	19174937
Bilateral acute angle closure glaucoma in a 50 year old female after oral administration of flavoxate.	2008-11	18754848
3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid.	2008-04-16	21202344
Persistence, adherence, and switch rates among extended-release and immediate-release overactive bladder medications in a regional managed care plan.	2008-04	18439051
[Clinical evaluation of supplemental administration of flavoxate hydrochloride in benign prostatic hyperplasia patients with nocturia resistant to an alpha1-adrenoceptor blocker].	2008-03	18411771
Effects of flavoxate hydrochloride on voltage-dependent Ba2+ currents in human detrusor myocytes at different experimental temperatures.	2007-11	17909749
Anticholinergic drugs versus other medications for overactive bladder syndrome in adults.	2007-10-17	17943782
Urodynamic evaluation in primary enuresis: an investigative and treatment outcome correlation.	2007-08	17496326
Anticholinergic drugs versus other medications for overactive bladder syndrome in adults.	2007-07-18	17636716
Agents for treatment of overactive bladder: a therapeutic class review.	2007-07	17637888
Drug-induced acute cholestatic liver damage in a patient with mutation of UGT1A1.	2007-07	17607296
High performance liquid chromatographic determination of 3-methylflavone-8-carboxylic acid, the main active metabolite of flavoxate hydrochloride in human urine.	2007-05-09	17349765
Effects of bladder training and/or tolterodine in female patients with overactive bladder syndrome: a prospective, randomized study.	2006-12	17179687
Canadian Urological Association guidelines on urinary incontinence.	2006-06	16813704
Conformational evaluation and detailed 1H and 13C NMR assignments of flavoxate, a urinary tract antispasmodic agent.	2006-05-03	16426792
The effects of flavoxate hydrochloride on voltage-dependent L-type Ca2+ currents in human urinary bladder.	2005-09	15965499
Persistence and adherence of medications for chronic overactive bladder/urinary incontinence in the california medicaid program.	2005-08-11	16091027
Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence.	2005-06	18360555
Activation of the rostral pontine reticular formation increases the spinal glycine level and inhibits bladder contraction in rats.	2005-05	15821593
The handling of urinary incontinence in Danish general practices after distribution of guidelines and voiding diary reimbursement: an observational study.	2004-06-29	15225353
[Alpha-blockers and bioflavonoids in men with chronic nonbacterial prostatitis (NIH-IIIa): a prospective, placebo-controlled trial].	2004-02	15132876
Bladder training for urinary incontinence in adults.	2004	14973967
[The medical treatment of overactive bladder].	2003-05	12746713
Clinical pharmacokinetics of drugs used to treat urge incontinence.	2003	14606931
Drug therapy of urinary urge incontinence: a systematic review.	2002-11	12423868
Incorrect assumption regarding the mechanism of action of flavoxate.	2002-02	12028232
Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients.	2002-01	12028256
Development of a high-performance liquid chromatographic method for bioequivalence study of flavoxate tablets.	2001-02-10	11232858
Association between oxybutynin and neuropsychiatric adverse effects not confirmed in daily practice.	2001-02	11207885

Patents

Sample Use Guides

In Vivo Use Guide

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

Unknown

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:13:53 GMT 2025` Edited by `admin` on `Wed Apr 02 09:13:53 GMT 2025`
Record UNII	3E74Y80MEY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BLADURIL

Preferred Name

English

FLAVOXATE

Official Name

English

FLAVOXATE [MI]

Common 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