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Identification
NameFlavoxate
Accession NumberDB01148  (APRD00972)
TypeSmall Molecule
GroupsApproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylateNot AvailableNot Available
2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylateNot AvailableNot Available
2-Piperidinoethyl 3-methylflavone-8-carboxylateNot AvailableNot Available
beta-Piperidinoethyl 3-methylflavone-8-carboxylateNot AvailableNot Available
FlavoxateNot AvailableNot Available
Flavoxate HCINot AvailableNot Available
FlavoxatoNot AvailableNot Available
FlavoxatumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flavoxate Hydrochloridetablet, film coated100 mgoralGlobal Pharmaceuticals2003-08-28Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet, film coated100 mgoralPaddock Laboratories, LLC2004-12-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet100 mgoralEpic Pharma, LLC2011-02-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet100 mgoralAv Pak2012-11-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet, film coated100 mgoralTAGI Pharma, Inc.2011-03-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet, film coated100 mgoralPhysicians Total Care, Inc.2012-01-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet100 mgoralGolden State Medical Supply, Inc.2011-02-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxate Hydrochloridetablet, film coated100 mgoralCarilion Materials Management2004-12-22Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flavoxatetablet200 mgoralPharmel IncNot AvailableNot AvailableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Over the Counter ProductsNot Available
International Brands
NameCompany
BladurilSanofi
FlavosertDaito
ProgutSanwa Kagaku
SawadaronSawai Seiyaku
UridronJohnson
UripaxFarmindustria
UrispasAdcock Ingram Pharmaceuticals
UroxalSandoz
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Flavoxate Hydrochloride
3717-88-2
Thumb
  • InChI Key: XOEVKNFZUQEERE-UHFFFAOYSA-N
  • Monoisotopic Mass: 427.155036032
  • Average Mass: 427.921
DBSALT000407
Categories
CAS number15301-69-6
WeightAverage: 391.4596
Monoisotopic: 391.178358293
Chemical FormulaC24H25NO4
InChI KeySPIUTQOUKAMGCX-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
Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • Flavone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Benzylether
  • Benzoyl
  • Pyranone
  • Benzenoid
  • Pyran
  • Piperidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis.
PharmacodynamicsFlavoxate 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 actionFlavoxate 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.
AbsorptionWell absorbed from gastrointestinal tract.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of elimination57% of the flavoxate HCl was excreted in the urine within 24 hours.
Half lifeNot Available
ClearanceNot Available
ToxicityThe 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateInhibitor0.796
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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tabletoral200 mg
Tablet, film coatedoral100 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point232-234U.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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

General ReferenceNot Available
External Links
ATC CodesG04BD02
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (241 KB)
Interactions
Drug Interactions
Drug
AclidiniumMay enhance the anticholinergic effect of Anticholinergic Agents.
ItoprideAnticholinergic Agents may diminish the therapeutic effect of Itopride.
MetoclopramideAnticholinergic Agents may diminish the therapeutic effect of Metoclopramide.
MianserinMay enhance the anticholinergic effect of Anticholinergic Agents.
MirabegronAnticholinergic Agents may enhance the adverse/toxic effect of Mirabegron.
Potassium ChlorideAnticholinergic Agents may enhance the ulcerogenic effect of Potassium Chloride.
PramlintideMay enhance the anticholinergic effect of Anticholinergic Agents. These effects are specific to the GI tract.
SecretinAnticholinergic Agents may diminish the therapeutic effect of Secretin.
TiotropiumAnticholinergic Agents may enhance the anticholinergic effect of Tiotropium.
TopiramateAnticholinergic Agents may enhance the adverse/toxic effect of Topiramate.
Food Interactions
  • Food may reduce irritation.
  • Take without regard to meals.

Targets

1. Muscarinic acetylcholine receptor M1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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
  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
  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

2. Muscarinic acetylcholine receptor M2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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
  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
  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. Pubmed
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on April 22, 2014 15:30