基本情報
- CAS
131986-45-3- 標準SMILES
CCCCCCOc1nsnc1C1=CCCN(C)C1- InChIKey
JOLJIIDDOBNFHW-UHFFFAOYSA-N- 分子式
- C14H23N3OS
- 平均分子量
- 281.42 g/mol
- 単同位体質量
- 281.15618354
概要
Xanomeline is a tetrahydropyridine and a member of thiadiazoles. It has a role as a serotonergic agonist and a muscarinic agonist.
名称と識別子
- 優先名称
- Xanomeline
- IUPAC
- 3-hexoxy-4-(1-methyl-3,6-dihydro-2H-pyridin-5-yl)-1,2,5-thiadiazole
- 現地名
- キサノメリン L-酒石酸 水和物
- 英語名
- Xanomeline
- 分子式
- C14H23N3OS
- 分子量
- 281.42
名称と別名
XANOMELINE131986-45-3LY-246708LY246708LY 246708xanomelina9ORI6L73CJ5-[4-(hexyloxy)-1,2,5-thiadiazol-3-yl]-1-methyl-1,2,3,6-tetrahydropyridineDTXSID60157286LY-246708 FREE BASECHEBI:100563-(4-hexoxy-1,2,5-thiadiazol-3-yl)-1-methyl-5,6-dihydro-2H-pyridine
名称をさらに表示
キサノメリン L-酒石酸 水和物キサノメリン3-ヘキシルオキシ-4-[(1-メチル-1,2,5,6-テトラヒドロピリジン)-3-イル]-1,2,5-チアジアゾールヘキシル[4-(1-メチル-1,2,5,6-テトラヒドロピリジン-3-イル)-1,2,5-チアジアゾール-3-イル]エーテル1,2,5,6-テトラヒドロ-1-メチル-3-[4-ヘキシルオキシ-1,2,5-チアジアゾール-3-イル]ピリジン5-[4-(ヘキシルオキシ)-1,2,5-チアジアゾール-3-イル]-1-メチル-1,2,3,6-テトラヒドロピリジンMemcorLomeronNNC-11-02323-(Hexyloxy)Xanomeline(LY-246708)JNJ-7777120 (Zanoterone)Xanomeline, 10 mM in DMSO
xanomelinum5-(4-(hexyloxy)-1,2,5-thiadiazol-3-yl)-1-methyl-1,2,3,6-tetrahydropyridineRefChem:195101DTXCID90797773-(3-O-hexyl-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine683-413-4(3-O-hexyloxy)-TZTP3-(Hexyloxy)-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1,2,5-thiadiazole
物性
構造計算による物性
- XLogP
- 3.3
- 極性表面積
- 66.5 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
- 7
- 重原子数
- 19
- 形式電荷
- 0
- 複雑度
- 298
実験および物理化学的性質
SolubilityHighly soluble
Human DrugsBreast Feeding; Lactation; Milk, Human; Antipsychotic Agents; Parasympathomimetics; Psychotropic Drugs; Muscarinic Agonists; Parasympatholytics; Muscarinic Antagonists
物理化学的性質
- 沸点
- 397 · 397.0±42.0 °C(Predicted)
- 比重(密度)
- 1.101 · 1.101±0.06 g/cm3(Predicted)
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 2 O: · H2O: 可溶10mg/mL、透明(加温)
- 外見
- 粉
- 酸解離定数(Pka)
- 7.34 · 7.34±0.40(Predicted)
- 色
- オフホワイト
- InChI
- InChI=1S/C14H23N3OS/c1-3-4-5-6-10-18-14-13(15-19-16-14)12-8-7-9-17(2)11-12/h8H,3-7,9-11H2,1-2H3
- InChIKey
- JOLJIIDDOBNFHW-UHFFFAOYSA-N
- SMILES
- C1N(C)CCC=C1C1C(OCCCCCC)=NSN=1
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。
GHS分類
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (100%)
毒性情報
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- wgk
- 3
化学と産業
薬理情報
Protein BindingXanomeline is approximately 95% protein bound in plasma.
Mechanism of Action
The efficacy of xanomeline in the treatment of schizophrenia is thought to be due to its agonist activity at muscarinic acetylcholine receptors M1 and M4 in the central nervous system. It binds to muscarinic receptors M1 to M5 with comparable affinity and exhibits relatively higher agonist activity at the M1 and M4 receptors.
Biological Half-LifeThe half-life of xanomeline is 5 hours.
Metabolism/Metabolites
Xanomeline is extensively metabolized, both by CYP450 enzymes - including CYP2D6, CYP2B6, CYP1A2, CYP2C9, and CYP2C19 - as well as flavin monooxygenases (FMO1 and FMO3). Unchanged parent drug accounts for <0.01% of drug product excreted in the urine.
FDA Pharmacological Classification
9ORI6L73CJ
XANOMELINE
Established Pharmacologic Class [EPC] - Cholinergic Muscarinic Agonist
Mechanisms of Action [MoA] - Cholinergic Muscarinic Agonists
Mechanisms of Action [MoA] - Cytochrome P450 3A4 Inhibitors
Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors
MeSH Pharmacological Classification
Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here.
A loosely defined grouping of drugs that have effects on psychological function. Here the psychotropic agents include the antidepressive agents, hallucinogens, and tranquilizing agents (including the antipsychotics and anti-anxiety agents).
Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate.
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