Flavoxate

Flavoxate
Systematic (IUPAC) name
2-(1-piperidyl)ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682706
Identifiers
CAS Number 15301-69-6 YesY
ATC code G04BD02 (WHO)
PubChem CID 3354
IUPHAR/BPS 7187
DrugBank DB01148 YesY
ChemSpider 3237 YesY
UNII 3E74Y80MEY YesY
KEGG D07961 YesY
ChEBI CHEBI:5088 YesY
ChEMBL CHEMBL1493 N
Chemical data
Formula C24H25NO4
Molar mass 391.46 g/mol
 NYesY (what is this?)  (verify)

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.

Clinical uses

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.

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.

Side effects

Flavoxate is generally well tolerated, but can potentially cause, vomiting, upset stomach, dry mouth or throat, blurred vision, eye pain,[1] and increased sensitivity of your eyes to light.

Contraindications

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.

Synthesis

Smooth muscle relaxant. Prepn of the hydrochloride:[2] P. Da Re, U.S. Patent 2,921,070 and U.S. Patent 3,350,411 (1960 to Recordati and 1967 to Seceph).

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.

See also

Notes

  1. ↑ Zakir SM, Zaka-ur-Rab S, Salman MT, Khan RA. Bilateral acute angle closure glaucoma in a 50-year-old female after oral administration of flavoxate. British Journal of Clinical Pharmacology. 2008. 66(5):726-727
  2. ↑ Re, P. D.; Verlicchi, L.; Setnikar, I. (1960). "Some Basic Derivatives of 3-Methylflavone-8-carboxylic Acid". Journal of Medicinal and Pharmaceutical Chemistry 2 (3): 263. doi:10.1021/jm50010a002.

References

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