Flavoxate

Flavoxate

Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a682706
ATC code	G04BD02 (WHO)
Identifiers
IUPAC name 2-(1-piperidyl)ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
CAS Number	15301-69-6 Y
PubChem CID	3354
IUPHAR/BPS	7187
DrugBank	DB01148 Y
ChemSpider	3237 Y
UNII	3E74Y80MEY
KEGG	D07961 Y
ChEBI	CHEBI:5088 Y
ChEMBL	CHEMBL1493 N
ECHA InfoCard	100.035.745
Chemical and physical data
Formula	C24H25NO4
Molar mass	391.46 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(OCCN1CCCCC1)c4cccc2c4O/C(=C(\C2=O)C)c3ccccc3
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 Y Key:SPIUTQOUKAMGCX-UHFFFAOYSA-N Y
NY (what is this?)

Flavoxate is an anticholinergic with antimuscarinic effects. Its muscle relaxant properties may be due to a direct action on the smooth muscle rather than by antagonizing muscarinic receptors.

Flavoxate is used to treat urinary bladder spasms. It is available under the trade name Urispas (Paladin),Genurin (by Recordati, Italy) in Italy and KSA,Uritac by El Saad company in Syria, under the name Bladderon by Nippon Shinyaku of Japan, or Bladuril in Chile, Utispas ( Apex Pharma) in Nepal.

Flavoxate is indicated for symptomatic relief of interstitial cystitis, dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis.

Flavoxate is generally well tolerated, but can potentially cause, vomiting, upset stomach, dry mouth or throat, blurred vision, eye pain, and increased sensitivity of your eyes to light.

Flavoxate is contraindicated in patients who have any of the following obstructive conditions: pyloric or duodenal obstruction, obstructive intestinal lesions or ileus, achalasia, gastrointestinal hemorrhage and obstructive uropathies of the lower urinary tract.

Nitration of hydroxypropiophenone (1) followed by conversion of the phenol to its methyl by means of MeI provides the intermediate 2; the nitro group is then reduced to the corresponding amine (3) by catalytic reduction. The newly formed amine is then replaced by a nitrile group by successive conversion to the diazonium salt by means of nitrous acid followed by treatment with cuprous cyanide (4). Rxn with aluminium chloride|AlCl₃]] cleaves the methyl ether to afford the ortho acylphenol (5). This is converted to the chromone/flavone (6) in a Kostanecki acylation rxn with BzCl and NaOBz. The nitrile is next hydrolyzed to the carboxylic acid (7) by means of SOCl₂ and that treated with β-Piperidylethanol. There is thus obtained flavoxate (8), a muscle relaxant whose name reflects its flavone nucleus.