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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
Salts
Name/CAS Structure Properties
Flavoxate Hydrochloride
3717-88-2
Thumb
  • InChI Key: XOEVKNFZUQEERE-UHFFFAOYSA-N
  • Monoisotopic Mass: 427.155036032
  • Average Mass: 427.921
DBSALT000407
Brand names
NameCompany
BladurilSanofi
FlavosertDaito
ProgutSanwa Kagaku
SawadaronSawai Seiyaku
UridronJohnson
UripaxFarmindustria
UrispasAdcock Ingram Pharmaceuticals
UroxalSandoz
Brand mixturesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassPhenylpropanoids and Polyketides
ClassFlavonoids
SubclassFlavones
Direct parentFlavones
Alternative parentsChromones; Benzoic Acid Esters; Benzylethers; Benzoyl Derivatives; Pyranones and Derivatives; Piperidines; Tertiary Amines; Carboxylic Acid Esters; Enolates; Polyamines; Dialkyl Ethers
Substituentschromone; benzopyran; benzoate ester; benzylether; benzoic acid or derivative; benzoyl; pyranone; piperidine; pyran; benzene; tertiary amine; carboxylic acid ester; dialkyl ether; enolate; carboxylic acid derivative; polyamine; ether; organonitrogen compound; amine
Classification descriptionThis compound belongs to the flavones. These are flavonoids whose structure is based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9851
Blood Brain Barrier + 0.9505
Caco-2 permeable + 0.5421
P-glycoprotein substrate Substrate 0.7553
P-glycoprotein inhibitor I Inhibitor 0.7986
P-glycoprotein inhibitor II Inhibitor 0.8388
Renal organic cation transporter Inhibitor 0.5166
CYP450 2C9 substrate Non-substrate 0.8398
CYP450 2D6 substrate Non-substrate 0.6898
CYP450 3A4 substrate Substrate 0.5522
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Inhibitor 0.796
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6708
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.9323
Biodegradation Not ready biodegradable 0.8989
Rat acute toxicity 2.2772 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Strong inhibitor 0.6988
hERG inhibition (predictor II) Non-inhibitor 0.6137
Pharmacoeconomics
Manufacturers
  • Epic pharma llc
  • Impax pharmaceuticals
  • Paddock laboratories inc
  • Ortho mcneil janssen pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
Prices
Unit descriptionCostUnit
Urispas 100 mg tablet1.79USDtablet
Flavoxate hcl 100 mg tablet1.49USDtablet
Apo-Flavoxate 200 mg Tablet0.76USDtablet
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 Solubility0.0154ALOGPS
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
Spectra
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
ResourceLink
KEGG CompoundC07809
PubChem Compound3354
PubChem Substance46505138
ChemSpider3237
ChEBI5088
ChEMBLCHEMBL1493
Therapeutic Targets DatabaseDAP001114
PharmGKBPA164781386
Drug Product Database2245480
RxListhttp://www.rxlist.com/cgi/generic3/flavoxate.htm
Drugs.comhttp://www.drugs.com/cdi/flavoxate.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/uri1471.shtml
WikipediaFlavoxate
ATC CodesG04BD02
AHFS Codes
  • 86:12.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(241 KB)
Interactions
Drug Interactions
Drug
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
RivastigminePossible antagonism of action
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Flavoxate, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Flavoxate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Flavoxate, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium and Flavoxate, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Food may reduce irritation.
  • Take without regard to meals.

Targets

1. 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

2. 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

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