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
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
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 |
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Target ID: CHEMBL2095219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10858873 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | FLAVOXATE HYDROCHLORIDE Approved UseFlavoxate 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 Date2004 |
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Palliative | FLAVOXATE HYDROCHLORIDE Approved UseFlavoxate 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 Date2004 |
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Palliative | FLAVOXATE HYDROCHLORIDE Approved UseFlavoxate 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 Date2004 |
Cmax
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 | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 |
T1/2
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: |
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 Sources: Edema hands |
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
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: |
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: |
PubMed
Title | Date | PubMed |
---|---|---|
Development of a high-performance liquid chromatographic method for bioequivalence study of flavoxate tablets. | 2001 Feb 10 |
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Urinary antispasmodic use and the risks of ventricular arrhythmia and sudden death in older patients. | 2002 Jan |
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[Alpha-blockers and bioflavonoids in men with chronic nonbacterial prostatitis (NIH-IIIa): a prospective, placebo-controlled trial]. | 2004 Feb |
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Trospium chloride: an update on a quaternary anticholinergic for treatment of urge urinary incontinence. | 2005 Jun |
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Urodynamic evaluation in primary enuresis: an investigative and treatment outcome correlation. | 2007 Aug |
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Agents for treatment of overactive bladder: a therapeutic class review. | 2007 Jul |
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Drug-induced acute cholestatic liver damage in a patient with mutation of UGT1A1. | 2007 Jul |
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Anticholinergic drugs versus other medications for overactive bladder syndrome in adults. | 2007 Jul 18 |
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High performance liquid chromatographic determination of 3-methylflavone-8-carboxylic acid, the main active metabolite of flavoxate hydrochloride in human urine. | 2007 May 9 |
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Effects of flavoxate hydrochloride on voltage-dependent Ba2+ currents in human detrusor myocytes at different experimental temperatures. | 2007 Nov |
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Anticholinergic drugs versus other medications for overactive bladder syndrome in adults. | 2007 Oct 17 |
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Persistence, adherence, and switch rates among extended-release and immediate-release overactive bladder medications in a regional managed care plan. | 2008 Apr |
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3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid. | 2008 Apr 16 |
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The role of combination medical therapy in benign prostatic hyperplasia. | 2008 Dec |
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[Clinical evaluation of supplemental administration of flavoxate hydrochloride in benign prostatic hyperplasia patients with nocturia resistant to an alpha1-adrenoceptor blocker]. | 2008 Mar |
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Clinical guidelines for overactive bladder. | 2009 Feb |
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Acute myocardial infarction and Kounis syndrome. | 2009 May 15 |
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Oxybutynin extended release for the management of overactive bladder: a clinical review. | 2009 Sep 21 |
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[Urinary incontinence and puppy coat due to spaying in the bitch. An overview of pathophysiology, diagnosis and therapy]. | 2010 Jun 8 |
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New insights into molecular targets for urinary incontinence. | 2010 Oct |
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4026456
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.
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G04BD02
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N0000000125
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N0000000125
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N0000175700
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WHO-VATC |
QG04BD02
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N0000000125
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NCI_THESAURUS |
C29704
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LIVERTOX |
NBK548911
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239-337-5
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m5398
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D005422
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FLAVOXATE
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CHEMBL1493
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)