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Flavoxate

Flavoxate structure

Flavoxate 

structure
  • CAS No:

    15301-69-6

  • Formula:

    C24H25NO4

  • Chemical Name:

    Flavoxate

  • Synonyms:

    4H-1-Benzopyran-8-carboxylic acid,3-methyl-4-oxo-2-phenyl-,2-(1-piperidinyl)ethyl ester;4H-1-Benzopyran-8-carboxylic acid,3-methyl-4-oxo-2-phenyl-,2-piperidinoethyl ester;Flavoxate;Piperidinoethyl 3-methyl-2-phenyl-4-oxo-4H-1-benzopyran-8-carboxylate;β-Piperidinoethyl-3-methylflavone-8-carboxylate;2-Piperidinoethyl 3-methylflavone-8-carboxylate

  • Categories:

    Active Pharmaceutical Ingredients  >  Urinary System Drugs

Description

ChEBI: A carboxylic ester resulting from the formal condensation of 3-methylflavone-8-carboxylic acid with 2-(1-piperidinyl)ethanol.


Solid


Flavoxate is a carboxylic ester resulting from the formal condensation of 3-methylflavone-8-carboxylic acid with 2-(1-piperidinyl)ethanol. It has a role as a parasympatholytic, a muscarinic antagonist and an antispasmodic drug. It is a member of piperidines, a member of flavones, a carboxylic ester and a tertiary amino compound. It derives from a 3-methylflavone-8-carboxylic acid and a 2-(piperidin-1-yl)ethanol. It is a conjugate base of a flavoxate(1+).|Flavoxate is a Cholinergic Muscarinic Antagonist. The mechanism of action of flavoxate is as a Cholinergic Muscarinic Antagonist.|Flavoxate is a synthetic anticholinergic agent that is used for treatment of urinary incontinence and overactive bladder syndrome. Flavoxate has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.|Flavoxate is a synthetic parasympatholytic with antimuscarinic, muscle relaxant and urinary antispasmodic properties. Flavoxate binds and inhibits muscarinic receptors, thereby suppressing the micturition reflex and increases urinary bladder capacity by modifying the micturition center in the brain stem. In addition, this agent has been found to inhibit cyclic AMP formation in striatal membranes of the brain through stimulation of pertussis toxin-sensitive G protein-coupled receptors which in turn suppress isovolumetric urinary bladder contraction.|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.

Flavoxate Basic Attributes

391.46

391.46

239-337-5

3E74Y80MEY

DTXSID3023053

C61765

G04BD02|G - Genito urinary system and sex hormones

Characteristics

55.8

4.4

Solid

1.203±0.06 g/cm3(Predicted)

87-88 °C

564.1±50.0 °C(Predicted)

294.9±30.1 °C

1.591

1.54e-02 g/L

9.56E-13mmHg at 25°C

LD50 in rats (mg/kg): 1110 orally; 20.8 i.v. (Setnikar, 1975)

7.3None

7.3

Toxicity

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.

Like other anticholinergic agents, flavoxate has not been linked to episodes of liver enzyme elevations or clinically apparent liver injury. A major reason for its safety may relate to the low daily dose.

Drug Information

For symptomatic relief of dysuria, urgency, nocturia, suprapubic pain, frequency and incontinence as may occur in cystitis, prostatitis, urethritis, urethrocystitis/urethrotrigonitis.

Flavoxate is a synthetic anticholinergic agent that is used for treatment of urinary incontinence and overactive bladder syndrome. Flavoxate has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury.

Anticholinergic Agents

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.

Drugs used in the treatment of urogenital conditions and diseases such as URINARY INCONTINENCE; PROSTATIC HYPERPLASIA; and ERECTILE DYSFUNCTION. (See all compounds classified as Urological Agents.)|Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

Well absorbed from gastrointestinal tract.|57% of the flavoxate HCl was excreted in the urine within 24 hours.

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.

Bladuril

Flavoxate Use and Manufacturing

Relaxant (smooth muscle).

Computed Properties

Molecular Weight:391.5
XLogP3:4.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:391.17835828
Monoisotopic Mass:391.17835828
Topological Polar Surface Area:55.8
Heavy Atom Count:29
Complexity:631
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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