Identification
- Summary
Flavoxate is a muscarinic antagonist and spasmolytic used for the symptomatic relief of conditions associated with lack of muscle control in the bladder, such as dysuria, urgency, and nocturia.
- Generic Name
- Flavoxate
- DrugBank Accession Number
- DB01148
- Background
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
Structure for Flavoxate (DB01148)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Cystitis Combination Product in combination with: Propyphenazone (DB13524) •••••••••••• ••••••• •••••• Symptomatic treatment of Cystitis •••••••••••• Used in combination for symptomatic treatment of Dysuria Combination Product in combination with: Propyphenazone (DB13524) •••••••••••• ••••••• •••••• Used as adjunct in combination for symptomatic treatment of Kidney stones Combination Product in combination with: Propyphenazone (DB13524) •••••••••••• ••••••• •••••• Used in combination for symptomatic treatment of Menstrual cramps Combination Product in combination with: Propyphenazone (DB13524) •••••••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
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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.
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans - 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
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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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Flavoxate which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Flavoxate which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Flavoxate which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Flavoxate which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Flavoxate which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Take with or without food. The absorption is unaffected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Flavoxate hydrochloride 9C05J6089W 3717-88-2 XOEVKNFZUQEERE-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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Flavoxate Tablet 200 mg Oral Pharmel Inc 1998-02-16 2016-10-26 Canada 
Urispas Tablet, film coated 100 mg/1 Oral Alza 1970-01-15 2009-03-30 US 
Urispas Tab 200mg Tablet 200 mg Oral Paladin Labs Inc. 1987-12-31 2021-07-28 Canada Urispas Tab 200mg Tablet 200 mg Oral Cedona Pharmaceuticals B.V. 1986-12-31 2009-07-28 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-flavoxate Tablet 200 mg Oral Apotex Corporation 2001-11-20 2019-12-02 Canada Flavoxate Hydrochloride Tablet 100 mg/1 Oral Av Pak 2012-11-30 Not applicable US Flavoxate Hydrochloride Tablet 100 mg/1 Oral Epic Pharma, LLC 2011-02-21 Not applicable US 
Flavoxate Hydrochloride Tablet, film coated 100 mg/1 Oral Physicians Total Care, Inc. 2012-01-04 Not applicable US 
Flavoxate Hydrochloride Tablet 100 mg/1 Oral PuraCap Laboratories LLC dba Blu Pharmaceuticals 2016-12-15 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image CISTALGAN Flavoxate (200 MG) + Propyphenazone (250 MG) Tablet, coated Oral Viatris Healthcare Limited 2014-07-08 Not applicable Italy 
Categories
- ATC Codes
- G04BD02 — Flavoxate
- Drug Categories
- Agents producing tachycardia
- Anticholinergic Agents
- Autonomic Agents
- Benzopyrans
- Chromones
- Drugs for Urinary Frequency and Incontinence
- Drugs that are Mainly Renally Excreted
- Flavones
- Flavonoids
- Genito Urinary System and Sex Hormones
- Genitourinary Agents
- Heterocyclic Compounds, Fused-Ring
- Muscarinic Antagonists
- Parasympatholytics
- Peripheral Nervous System Agents
- Pyrans
- Urological Agents
- Urologicals
- 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)
- Affected organisms
- Humans and other mammals
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
- External Links
- Human Metabolome Database
- HMDB0015279
- KEGG Compound
- C07809
- PubChem Compound
- 3354
- PubChem Substance
- 46505138
- ChemSpider
- 3237
- 4440
- ChEBI
- 5088
- ChEMBL
- CHEMBL1493
- ZINC
- ZINC000000608382
- Therapeutic Targets Database
- DAP001114
- PharmGKB
- PA164781386
- PDBe Ligand
- HWL
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Flavoxate
- PDB Entries
- 7e4a
- MSDS
- Download (241 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Pain 1 1 Completed Treatment Healthy Subjects (HS) 1
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
Form Route Strength Tablet, coated Oral Tablet Oral 100 mg/1 Tablet, film coated Oral 100 mg/1 Tablet, coated Oral 20000000 mg Suppository 100 MG Suppository 200 MG Tablet, coated Oral Tablet, film coated Oral Tablet, film coated Oral 200 mg Tablet Oral 200 mg Tablet Oral Tablet Oral 100 mg Tablet, film coated Oral 100 mg Tablet, coated Oral 100 mg Tablet, coated Oral 200 mg Tablet, sugar coated Oral 200 mg - Prices
Unit description Cost Unit Urispas 100 mg tablet 1.79USD tablet Flavoxate hcl 100 mg tablet 1.49USD tablet Apo-Flavoxate 200 mg Tablet 0.76USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 232-234 U.S. Patent 2,921,070 water solubility 10 mg/L (at 37 °C) MERCK INDEX (1996) logP 4.4 Not Available pKa 7.3 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.0154 mg/mL ALOGPS logP 3.65 ALOGPS logP 4.24 Chemaxon logS -4.4 ALOGPS pKa (Strongest Basic) 7.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 55.84 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 113.51 m3·mol-1 Chemaxon Polarizability 43.39 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-01ot-9440000000-61df15b695a5a5f45ed3 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0109000000-13c841a722ee721fc645 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0419000000-944be0bd6a7a666d4176 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-01ox-0239000000-14a364d21f4496d4733e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-002r-0293000000-9282c7740c64e271a1a7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-1393000000-2da34fb371c544cb1225 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001r-0691000000-28ee32ee06cfcda78698 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 202.3813408 predictedDarkChem Lite v0.1.0 [M-H]- 191.44054 predictedDeepCCS 1.0 (2019) [M+H]+ 202.7771408 predictedDarkChem Lite v0.1.0 [M+H]+ 193.79854 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.4861408 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.79472 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55