Flavoxate

Identification

Name
Flavoxate
Accession Number
DB01148
Description

A drug that has been used in various urinary syndromes and as an antispasmodic. Its therapeutic usefulness and its mechanism of action are not clear. It may have local anesthetic activity and direct relaxing effects on smooth muscle as well as some activity as a muscarinic antagonist. [PubChem]

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 391.4596
Monoisotopic: 391.178358293
Chemical Formula
C24H25NO4
Synonyms
  • 2-(1-piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate
  • 2-piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate
  • 2-piperidinoethyl 3-methylflavone-8-carboxylate
  • Flavoxate
  • Flavoxato
  • Flavoxatum
  • β-piperidinoethyl 3-methylflavone-8-carboxylate

Pharmacology

Indication

For symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Flavoxate is a spasmolytic flavone derivative that acts by relaxing the smooth muscle in the urinary tract. Flavoxate is a competitive muscarinic receptor antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. Muscarinic receptors play an important role in several major cholin-ergically mediated functions, including contractions of urinary bladder smooth muscle and stimulation of salivary secretion.

Mechanism of action

Flavoxate 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, urge incontinence episodes, urge severity and improving retention, facilitating increased volume per void.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M2
antagonist
Humans
AMuscarinic acetylcholine receptor M1
antagonist
Humans
Absorption

Well absorbed from gastrointestinal tract.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

57% of the flavoxate HCl was excreted in the urine within 24 hours.

Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

The oral LD50 for flavoxate HCl in rats is 4273 mg/kg. The oral LD50 for flavoxate HCl in mice is 1837 mg/kg. Symptoms of overdose include convulsions, decreased ability to sweat, (warm, red skin, dry mouth, and increased body temperature), hallucinations, increased heart rate and blood pressure, and mental confusion.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Flavoxate which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Flavoxate which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Flavoxate which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Flavoxate which could result in a higher serum level.
AcetaminophenAcetaminophen may decrease the excretion rate of Flavoxate which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Flavoxate.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Flavoxate.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Flavoxate which could result in a higher serum level.
AclidiniumThe risk or severity of adverse effects can be increased when Flavoxate is combined with Aclidinium.
AcrivastineFlavoxate may decrease the excretion rate of Acrivastine which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. The absorption is unaffected by food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Flavoxate hydrochloride9C05J6089W3717-88-2XOEVKNFZUQEERE-UHFFFAOYSA-N
Product Images
International/Other Brands
Bladuril (Sanofi) / Flavosert (Daito) / Progut (Sanwa Kagaku) / Sawadaron (Sawai Seiyaku) / Uridron (Johnson) / Uripax (Farmindustria) / Uroxal (Sandoz)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
FlavoxateTabletOralPharmel Inc1998-02-162016-10-26Canada flag
UrispasTablet, film coated100 mg/1OralAlza1970-01-152009-03-30US flag
Urispas Tab 200mgTabletOralCedona Pharmaceuticals B.V.1986-12-312009-07-28Canada flag
Urispas Tab 200mgTabletOralPaladin Labs Inc1987-12-31Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-flavoxateTabletOralApotex Corporation2001-11-202019-12-02Canada flag
Flavoxate HydrochlorideTablet100 mg/1OralPuraCap Laboratories LLC dba Blu Pharmaceuticals2016-12-15Not applicableUS flag
Flavoxate HydrochlorideTablet, film coated100 mg/1OralTAGI Pharma, Inc.2011-03-252020-03-31US flag
Flavoxate HydrochlorideTablet, film coated100 mg/1OralCarilion Materials Management2004-12-22Not applicableUS flag
Flavoxate HydrochlorideTablet100 mg/1OralGolden State Medical Supply, Inc.2011-02-212014-05-31US flag
Flavoxate HydrochlorideTablet, film coated100 mg/1OralPaddock Laboratories, LLC2004-12-22Not applicableUS flag
Flavoxate HydrochlorideTablet100 mg/1OralAv Pak2012-11-30Not applicableUS flag
Flavoxate HydrochlorideTablet100 mg/1OralEpic Pharma, LLC2011-02-21Not applicableUS flag42806 0058 01 nlmimage10 a14a50e2
Flavoxate HydrochlorideTablet, film coated100 mg/1OralPhysicians Total Care, Inc.2012-01-04Not applicableUS flag54868 632620180907 15195 1nbwjw
Flavoxate HydrochlorideTablet, film coated100 mg/1OralImpax Generics2003-08-282016-12-09US flag00115 1811 01 nlmimage10 ff07ffef
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
G04BD02 — Flavoxate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavones
Direct Parent
Flavones
Alternative Parents
Chromones / Pyranones and derivatives / Piperidines / Benzene and substituted derivatives / Heteroaromatic compounds / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Oxacyclic compounds / Monocarboxylic acids and derivatives
show 5 more
Substituents
1-benzopyran / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzopyran / Carboxylic acid derivative / Carboxylic acid ester / Chromone
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidines, tertiary amino compound, carboxylic ester, flavones (CHEBI:5088)

Chemical Identifiers

UNII
3E74Y80MEY
CAS number
15301-69-6
InChI Key
SPIUTQOUKAMGCX-UHFFFAOYSA-N
InChI
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
IUPAC Name
2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate
SMILES
CC1=C(OC2=C(C=CC=C2C(=O)OCCN2CCCCC2)C1=O)C1=CC=CC=C1

References

Synthesis Reference

Da Re, P.; U.S. Patent 2,921,070; January 12, 1960; assigned to Recordati-Laboratorio Farmacologico SPA, Italy.

General References
Not Available
Human Metabolome Database
HMDB0015279
KEGG Compound
C07809
PubChem Compound
3354
PubChem Substance
46505138
ChemSpider
3237
RxNav
4440
ChEBI
5088
ChEMBL
CHEMBL1493
ZINC
ZINC000000608382
Therapeutic Targets Database
DAP001114
PharmGKB
PA164781386
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Flavoxate
AHFS Codes
  • 86:12.04 — Antimuscarinics
MSDS
Download (241 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPain1
1CompletedTreatmentHealthy Volunteers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Alza Corp.
  • Cardinal Health
  • Catalent Pharma Solutions
  • Global Pharmaceuticals
  • Kaiser Foundation Hospital
  • McNeil Laboratories
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Paddock Labs
  • PD-Rx Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
Tablet, coatedOral200 mg
Tablet100 mg
TabletOral100 mg/1
Tablet, film coatedOral100 mg/1
Tablet, coatedOral100 mg
Tablet, film coated200 mg
TabletOral
Tablet
Tablet, film coatedOral
Prices
Unit descriptionCostUnit
Urispas 100 mg tablet1.79USD tablet
Flavoxate hcl 100 mg tablet1.49USD tablet
Apo-Flavoxate 200 mg Tablet0.76USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)232-234U.S. Patent 2,921,070
water solubility10 mg/L (at 37 °C)MERCK INDEX (1996)
logP4.4Not Available
pKa7.3MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.0154 mg/mLALOGPS
logP3.65ALOGPS
logP4.24ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)7.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity113.51 m3·mol-1ChemAxon
Polarizability43.39 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9851
Blood Brain Barrier+0.9505
Caco-2 permeable+0.5421
P-glycoprotein substrateSubstrate0.7553
P-glycoprotein inhibitor IInhibitor0.7986
P-glycoprotein inhibitor IIInhibitor0.8388
Renal organic cation transporterInhibitor0.5166
CYP450 2C9 substrateNon-substrate0.8398
CYP450 2D6 substrateNon-substrate0.6898
CYP450 3A4 substrateSubstrate0.5522
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6708
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9323
BiodegradationNot ready biodegradable0.8989
Rat acute toxicity2.2772 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6988
hERG inhibition (predictor II)Non-inhibitor0.6137
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Greco KA, McVary KT: The role of combination medical therapy in benign prostatic hyperplasia. Int J Impot Res. 2008 Dec;20 Suppl 3:S33-43. doi: 10.1038/ijir.2008.51. [PubMed:19002123]
  4. Uckert S, Stief CG, Odenthal KP, Truss MC, Lietz B, Jonas U: Responses of isolated normal human detrusor muscle to various spasmolytic drugs commonly used in the treatment of the overactive bladder. Arzneimittelforschung. 2000 May;50(5):456-60. [PubMed:10858873]
  5. Abbiati GA, Ceserani R, Nardi D, Pietra C, Testa R: Receptor binding studies of the flavone, REC 15/2053, and other bladder spasmolytics. Pharm Res. 1988 Jul;5(7):430-3. [PubMed:3247311]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Abbiati GA, Ceserani R, Nardi D, Pietra C, Testa R: Receptor binding studies of the flavone, REC 15/2053, and other bladder spasmolytics. Pharm Res. 1988 Jul;5(7):430-3. [PubMed:3247311]

Drug created on June 13, 2005 07:24 / Updated on October 27, 2020 11:13

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