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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
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
beta-Piperidinoethyl 3-methylflavone-8-carboxylate
Flavoxate
Flavoxate HCI
Flavoxato
Flavoxatum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Flavoxatetablet200 mgoralPharmel Inc1998-02-16Not applicableCanada
PMS-flavoxatetablet200 mgoralPharmascience Inc2002-07-24Not applicableCanada
Urispas Tab 200mgtablet200 mgoralCedona Pharmaceuticals B.V.1986-12-312009-07-28Canada
Urispas Tab 200mgtablet200 mgoralPaladin Labs Inc1987-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-flavoxatetablet200 mgoralApotex Inc2001-11-20Not applicableCanada
Flavoxate Hydrochloridetablet, film coated100 mg/1oralGlobal Pharmaceuticals2003-08-28Not applicableUs
Flavoxate Hydrochloridetablet100 mg/1oralGolden State Medical Supply, Inc.2011-02-21Not applicableUs
Flavoxate Hydrochloridetablet, film coated100 mg/1oralPhysicians Total Care, Inc.2012-01-04Not applicableUs
Flavoxate Hydrochloridetablet, film coated100 mg/1oralTAGI Pharma, Inc.2011-03-25Not applicableUs
Flavoxate Hydrochloridetablet100 mg/1oralAv Pak2012-11-30Not applicableUs
Flavoxate Hydrochloridetablet100 mg/1oralEpic Pharma, LLC2011-02-21Not applicableUs
Flavoxate Hydrochloridetablet, film coated100 mg/1oralPaddock Laboratories, LLC2004-12-22Not applicableUs
Flavoxate Hydrochloridetablet, film coated100 mg/1oralCarilion Materials Management2004-12-22Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not 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
UNII3E74Y80MEY
CAS number15301-69-6
WeightAverage: 391.4596
Monoisotopic: 391.178358293
Chemical FormulaC24H25NO4
InChI KeyInChIKey=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
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.
Related Articles
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 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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Tabletoral200 mg
Tabletoral100 mg/1
Tablet, film coatedoral100 mg/1
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 ReferencesNot Available
External Links
ATC CodesG04BD02
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (241 KB)
Interactions
Drug Interactions
Drug
AclidiniumAclidinium may increase the anticholinergic activities of Flavoxate.
Botulinum Toxin Type AFlavoxate may increase the anticholinergic activities of Botulinum Toxin Type A.
Botulinum Toxin Type BFlavoxate may increase the anticholinergic activities of Botulinum Toxin Type B.
Cimetropium BromideFlavoxate may increase the anticholinergic activities of Cimetropium Bromide.
DronabinolFlavoxate may increase the tachycardic activities of Dronabinol.
EluxadolineFlavoxate may increase the activities of Eluxadoline.
Glucagon recombinantThe risk or severity of adverse effects can be increased when Flavoxate is combined with Glucagon recombinant.
Ipratropium bromideIpratropium bromide may increase the anticholinergic activities of Flavoxate.
ItoprideThe therapeutic efficacy of Itopride can be decreased when used in combination with Flavoxate.
MianserinMianserin may increase the anticholinergic activities of Flavoxate.
MirabegronThe risk or severity of adverse effects can be increased when Flavoxate is combined with Mirabegron.
MorphineThe risk or severity of adverse effects can be increased when Flavoxate is combined with Morphine.
Potassium ChlorideFlavoxate may increase the ulcerogenic activities of Potassium Chloride.
PramlintidePramlintide may increase the anticholinergic activities of Flavoxate.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Flavoxate.
RamosetronFlavoxate may increase the activities of Ramosetron.
SecretinThe therapeutic efficacy of Secretin can be decreased when used in combination with Flavoxate.
SulpirideThe therapeutic efficacy of Sulpiride can be decreased when used in combination with Flavoxate.
TacrineThe therapeutic efficacy of Flavoxate can be decreased when used in combination with Tacrine.
TiotropiumFlavoxate may increase the anticholinergic activities of Tiotropium.
TopiramateThe risk or severity of adverse effects can be increased when Flavoxate is combined with Topiramate.
TrichlormethiazideThe serum concentration of Trichlormethiazide can be increased when it is combined with Flavoxate.
UmeclidiniumUmeclidinium may increase the anticholinergic activities of Flavoxate.
Food Interactions
  • Food may reduce irritation.
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
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 action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
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 ]
Kind
Protein
Organism
Human
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 action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
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 ]
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Drug created on June 13, 2005 07:24 / Updated on April 22, 2014 15:30