Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H25NO4.ClH |
Molecular Weight | 427.921 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=C(OC2=C(C=CC=C2C(=O)OCCN3CCCCC3)C1=O)C4=CC=CC=C4
InChI
InChIKey=XOEVKNFZUQEERE-UHFFFAOYSA-N
InChI=1S/C24H25NO4.ClH/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;1H
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 |
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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 |
---|---|---|
Association between oxybutynin and neuropsychiatric adverse effects not confirmed in daily practice. | 2001 Feb |
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Development of a high-performance liquid chromatographic method for bioequivalence study of flavoxate tablets. | 2001 Feb 10 |
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Incorrect assumption regarding the mechanism of action of flavoxate. | 2002 Feb |
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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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Clinical pharmacokinetics of drugs used to treat urge incontinence. | 2003 |
|
[Alpha-blockers and bioflavonoids in men with chronic nonbacterial prostatitis (NIH-IIIa): a prospective, placebo-controlled trial]. | 2004 Feb |
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The handling of urinary incontinence in Danish general practices after distribution of guidelines and voiding diary reimbursement: an observational study. | 2004 Jun 29 |
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Persistence and adherence of medications for chronic overactive bladder/urinary incontinence in the california medicaid program. | 2005 Jul-Aug |
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Activation of the rostral pontine reticular formation increases the spinal glycine level and inhibits bladder contraction in rats. | 2005 May |
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Conformational evaluation and detailed 1H and 13C NMR assignments of flavoxate, a urinary tract antispasmodic agent. | 2006 May 3 |
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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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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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High-performance liquid chromatographic determination of flavoxate hydrochloride and its hydrolysis product. | 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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Bilateral acute angle closure glaucoma in a 50 year old female after oral administration of flavoxate. | 2008 Nov |
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[Summary of the practice guideline 'Urinary incontinence' (first revision) from the Dutch College of General Practitioners]. | 2008 Nov 22 |
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Polymeric matrix membrane sensors for stability-indicating potentiometric determination of oxybutynin hydrochloride and flavoxate hydrochloride urogenital system drugs. | 2008 Nov-Dec |
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Liquid chromatographic fingerprint of 3-methylflavone-8-carboxylic acid established for its synthesis control analysis. | 2009 Mar 15 |
|
Liquid Chromatographic Determination of Flavoxate HCl in Pharmaceutical Formulation. | 2010 Jul |
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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NCI_THESAURUS |
C29704
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m5398
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100000091079
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ACTIVE MOIETY
SUBSTANCE RECORD