基本情報
- CAS
15301-69-6- 標準SMILES
Cc1c(-c2ccccc2)oc2c(C(=O)OCCN3CCCCC3)cccc2c1=O- InChIKey
SPIUTQOUKAMGCX-UHFFFAOYSA-N- 分子式
- C24H25NO4
- 平均分子量
- 391.5 g/mol
- 単同位体質量
- 391.17835828
概要
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+).
名称と識別子
- 優先名称
- Flavoxate
- IUPAC
- 2-piperidin-1-ylethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate
- 現地名
- フラボキサート
- 英語名
- FLAVOXATE
- 分子式
- C24H25NO4
- 分子量
- 391.46
名称と別名
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
名称をさらに表示
3-メチル-4-オキソ-2-フェニル-4H-1-ベンゾピラン-8-カルボン酸2-ピペリジノエチルフラボキサート3-メチル-4-オキソ-2-フェニル-4H-1-ベンゾピラン-8-カルボン酸2-(1-ピペリジニル)エチルフラボキサ-ト2-(ピペリジン-1-イル)エチル 3-メチル-4-オキソ-2-フェニル-4H-クロメン-8-カルボキシラート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
物性
構造計算による物性
- XLogP
- 4.3
- 極性表面積
- 55.8 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 5
- 回転可能結合数
- 6
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 631
実験および物理化学的性質
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
物理化学的性質
- 融点
- 87 · 87-88 °C
- 沸点
- 564.1 · 564.1±50.0 °C(Predicted)
- 比重(密度)
- 1.203 · 1.203±0.06 g/cm3(Predicted)
- 酸解離定数(Pka)
- 7.3 · 7.3(at 25℃)
- 外見
- オフホワイトの固体。
- 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
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
毒性情報
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
安全データ
- 毒性
- LD50 in rats (mg/kg): 1110 orally; 20.8 i.v. (Setnikar, 1975)
化学と産業
薬理情報
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.
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