Flavoxate

Common Name

Flavoxate Description

A drug that has been used in various urinary syndromes and as an antispasmodic. Its therapeutic usefliness 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

Synonyms

Value Source 2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylateChEBI 2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylateChEBI 2-Piperidinoethyl 3-methylflavone-8-carboxylateChEBI beta-Piperidinoethyl 3-methylflavone-8-carboxylateChEBI FlavoxatoChEBI FlavoxatumChEBI 2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acidGenerator Flavoxic acidGenerator 2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acidGenerator 2-Piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator b-Piperidinoethyl 3-methylflavone-8-carboxylateGenerator b-Piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator beta-Piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator β-piperidinoethyl 3-methylflavone-8-carboxylateGenerator β-piperidinoethyl 3-methylflavone-8-carboxylic acidGenerator Flavoxate hciHMDB ortho Brand OF flavoxate hydrochlorideMeSH UronidMeSH Byk brand OF flavoxate hydrochlorideMeSH Hydrochloride, flavoxateMeSH Shire brand OF flavoxate hydrochlorideMeSH BladurilMeSH Flavoxate hydrochlorideMeSH Pierre fabre brand OF flavoxate hydrochlorideMeSH Recordati brand OF flavoxate hydrochlorideMeSH Cahill may roberts brand OF flavoxate hydrochlorideMeSH Hoechst brand OF flavoxate hydrochlorideMeSH Negma brand OF flavoxate hydrochlorideMeSH SpasuretMeSH UrispasMeSH

Chemical Formlia

C₂₄H₂₅NO₄ Average Molecliar Weight

391.4596 Monoisotopic Molecliar Weight

391.178358293 IUPAC Name

2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate Traditional Name

flavoxate CAS Registry Number

15301-69-6 SMILES

InChI Identifier

InChI Key

SPIUTQOUKAMGCX-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Phenylpropanoids and polyketides Sub Class

Flavonoids 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

Azacyclic compounds

Organopnictogen compounds

Organooxygen compounds

Organic oxides

Hydrocarbon derivatives

Substituents

Flavone

Chromone

Benzopyran

1-benzopyran

Pyranone

Monocyclic benzene moiety

Piperidine

Pyran

Benzenoid

Heteroaromatic compound

Tertiary aliphatic amine

Tertiary amine

Amino acid or derivatives

Carboxylic acid ester

Oxacycle

Azacycle

Organoheterocyclic compound

Carboxylic acid derivative

Monocarboxylic acid or derivatives

Amine

Organopnictogen compound

Organic oxygen compound

Organonitrogen compound

Organooxygen compound

Organic nitrogen compound

Organic oxide

Hydrocarbon derivative

Aromatic heteropolycyclic compound

Molecliar Framework

Aromatic heteropolycyclic compounds External Descriptors

piperidines (CHEBI:5088 )

tertiary amino compound (CHEBI:5088 )

carboxylic ester (CHEBI:5088 )

flavones (CHEBI:5088 )

Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Parasympatholytics

Application

Pharmaceutical

Cellliar locations

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.54e-02 g/LNot Available LogP4.4Not Available

Predicted Properties

Property Value Source Water Solubility0.015 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 ŲChemAxon Rotatable Bond Count6ChemAxon Refractivity113.51 m³·mol^-1ChemAxon Polarizability43.39 ųChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01148

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01148

21059682

details

Abnormal Concentrations

Not Available Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB01148 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

3237 KEGG Compound ID

C07809 BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Flavoxate NuGOwiki Link

HMDB15279 Metagene Link

HMDB15279 METLIN ID

Not Available PubChem Compound

3354 PDB ID

Not Available ChEBI ID

5088

Product: HDAOS

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

Enzymes

General function:

Involved in G-protein coupled receptor protein signaling pathway

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:

51420.4

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 ]

General function:

Involved in G-protein coupled receptor protein signaling pathway

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

Gene Name:

CHRM2

Uniprot ID:

P08172

Molecular weight:

51714.6

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 ]

PMID: 19818703

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