Basic information
- CAS
15301-69-6- Standard SMILES
Cc1c(-c2ccccc2)oc2c(C(=O)OCCN3CCCCC3)cccc2c1=O- InChIKey
SPIUTQOUKAMGCX-UHFFFAOYSA-N- Molecular formula
- C24H25NO4
- Average molar mass
- 391.5 g/mol
- Monoisotopic mass
- 391.17835828
Overview
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 muscarinic antagonist, a parasympatholytic and an antispasmodic drug. It is a member of flavones, a member of piperidines, a carboxylic ester and a tertiary amino compound. It is functionally related to a 3-methylflavone-8-carboxylic acid and a 2-(piperidin-1-yl)ethanol. It is a conjugate base of a flavoxate(1+).
Names & identifiers
- Preferred name
- Flavoxate
- IUPAC
- 2-piperidin-1-ylethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
- English name
- FLAVOXATE
- Molecular formula
- C24H25NO4
- Molecular weight
- 391.46
Names & synonyms
flavoxate15301-69-6FlavoxatoFlavoxatum2-(piperidin-1-yl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylateBladuril4H-1-Benzopyran-8-carboxylic acid, 3-methyl-4-oxo-2-phenyl-, 2-(1-piperidinyl)ethyl ester3E74Y80MEY2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylate2-piperidinoethyl 3-methylflavone-8-carboxylatebeta-piperidinoethyl 3-methylflavone-8-carboxylate2-(1-Piperidinyl)ethyl 3-methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylate
Show more names
UronidFlavoxate-d5DW61 free baseFLAVOXATE USP/EP/BPRec-7-0040 free basePiperidinoethyl 3-methyl-2-phenyl-4-oxo-4H-1-benzopyran-8-carboxylate
2-Piperidinoethyl 3-methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylatCHEBI:5088DTXSID3023053RefChem:56748DTXCID003053G04BD02239-337-52-piperidin-1-ylethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 631
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Used in Switzerland
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
4.4
3.42
Solubility1.54e-02 g/L
Human DrugsBreast Feeding; Lactation; Muscarinic Antagonists; Parasympatholytics; Urological Agents
Melting Point232-234
Physical DescriptionSolid
Dissociation Constants7.3
Physicochemical properties
- Melting point
- 87 · 87-88 °C
- Boiling point
- 564.1 · 564.1±50.0 °C(Predicted)
- Density
- 1.203 · 1.203±0.06 g/cm3(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
HepatotoxicityLike 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 Induced Liver Injury
Benchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)
flavoxate
Urispas®
Antispasmodics
Not Applicable
no-DILI-concern
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Toxicity
- LD50 in rats (mg/kg): 1110 orally; 20.8 i.v. (Setnikar, 1975)
Chemistry & industry
Pharmacology
ATC Code
G04BD02
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
Pharmacodynamics
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.
FDA Pharmacological Classification
3E74Y80MEY
FLAVOXATE
Established Pharmacologic Class [EPC] - Cholinergic Muscarinic Antagonist
Mechanisms of Action [MoA] - Cholinergic Muscarinic Antagonists
Flavoxate is a Cholinergic Muscarinic Antagonist. The mechanism of action of flavoxate is as a Cholinergic Muscarinic Antagonist.
MeSH Pharmacological Classification
Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS.
Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.
Absorption, Distribution and Excretion
Well absorbed from gastrointestinal tract.
57% of the flavoxate HCl was excreted in the urine within 24 hours.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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