基本情報
- CAS
26615-21-4- 標準SMILES
CN(C)CCOC1=Cc2ccccc2Sc2ccc(Cl)cc21- InChIKey
HDOZVRUNCMBHFH-UHFFFAOYSA-N- 分子式
- C18H18ClNOS
- 平均分子量
- 331.9 g/mol
- 単同位体質量
- 331.0797631
概要
Zotepine is a dibenzothiepine and a tertiary amino compound. It has a role as a serotonergic drug, an alpha-adrenergic drug and a second generation antipsychotic.
名称と識別子
- 優先名称
- Zotepine
- IUPAC
- 2-(3-chlorobenzo[b][1]benzothiepin-5-yl)oxy-N,N-dimethylethanamine
- 現地名
- ゾテピン
- 英語名
- ZOTEPINE
- 分子式
- C18H18ClNOS
- 分子量
- 331.86
名称と別名
zotepine26615-21-4NipoleptLodopinZotepinaSetousZotepinumZotepinDTXSID90237562-[(8-chlorodibenzo[b,f]thiepin-10-yl)oxy]-N,N-dimethylethanamine2-Chloro-11-(2-(dimethylamino)ethoxy)dibenzo(b,f)thiepinU29O83JAZW
名称をさらに表示
2-[(8-クロロジベンゾ[b,f]チエピン-10-イル)オキシ]-N,N-ジメチルエタンアミンロシゾピロンメジャピン8-クロロ-10-[2-(ジメチルアミノ)エトキシ]ジベンゾ[b,f]チエピンセトウスロドピンゾテピンN,N-ジメチル-2-(2-クロロジベンゾ[b,f]チエピン-11-イルオキシ)エチルアミン2‐[(8‐クロロジベンゾ[B,F]チエピン‐10‐イル)オキシ]‐N,N‐ジメチルエタンアミンゾテピン (JAN)[2-({6-クロロ-2-チアトリシクロ[9.4.0.03,8]ペンタデカ-1(15),3,5,7,9,11,13-ヘプタエン-9-イル}オキシ)エチル]ジメチルアミン(ring-dMajorpinEtoxazole Impurity 9Zotepine, 10 mM in DMSO8-Chloro-10-[2-(dimethylamino)ethoxy]dibenzo[b,f]thiepinf)thiepin,2-chloro-11-(2-(dimethylamino)ethoxy)-dibenzo(
DTXCID603756CHEBI:323162-((8-Chlorodibenzo(b,f)thiepin-10-yl)oxy)-N,N-dimethylethanamine2-(8-chlorobenzo(b)(1)benzothiepin-6-yl)oxy-N,N-dimethylethanamine2-(8-chlorobenzo[b][1]benzothiepin-6-yl)oxy-N,N-dimethylethanamineZoleptil 25Zoleptil 50Zoleptil 100
物性
構造計算による物性
- XLogP
- 4.8
- 極性表面積
- 37.8 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 4
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 401
実験および物理化学的性質
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
SolubilityPoorly soluble
Boiling Point478.4ºC
Melting Point90ºC
物理化学的性質
- 融点
- 90 · 90-91°
- 沸点
- 478.4 · 478.4±45.0 °C(Predicted)
- 比重(密度)
- 1.0675 · 1.0675 (rough estimate)
- 屈折率
- 1.61 · 1.6100 (estimate)
- 貯蔵温度
- Store at RT
- 溶解性
- 20 mg/mL以上 · DMSO：20mg/mL以上
- 外見
- 粉
- 酸解離定数(Pka)
- 8.72 · 8.72±0.28(Predicted)
- 色
- ホワイトからオフホワイト
- InChI
- 1S/C18H18ClNOS/c1-20(2)9-10-21-16-11-13-5-3-4-6-17(13)22-18-8-7-14(19)12-15(16)18/h3-8,11-12H,9-10H2,1-2H3
- InChIKey
- HDOZVRUNCMBHFH-UHFFFAOYSA-N
- SMILES
- CN(C)CCOC1=Cc2ccccc2Sc3ccc(Cl)cc13
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, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H361: Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
危険有害性情報
Hazard Classes and Categories
Acute Tox. 4 (100%)
Reproductive toxicity - Category 2, Additional category: Effects on or via lactation
安全データ
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- 毒性
- LD50 in male mice, rats (mg/kg): 108, 458 orally; 43.3, 39.7 i.v.; 40.0, 97.0 i.p.; 84.9, 2080 s.c. (Fukuhara)
- risk_code
- 25-50/53
- hazard_code
- T
- safety_code
- 45-60-61
- Hazard Classifications
- Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
N - Nervous system
QN - Nervous system
Protein BindingPlasma protein binding of zotepine and its major active metabolite norzotepine account for 97% of the administered dose.
Pharmacodynamics
In preclinical studies, zotepine is characterized by the presence of a strong antiserotonergic activity when compared with other neuroleptic drugs. It has also been reported to present elevations in the seizure threshold in the amygdaloid nucleus. When zotepine's effects were analyzed by electroencephalography, it was noted a typical response of a low-potency neuroleptics of the sedative type. Administration of zotepine has shown improvements in numerical movements and complex reaction. These effects tend to be accompanied by increases in pulse rate, increase in prolactin levels and some typical neuroleptic side effects.
Mechanism of Action
Zotepine is a dopamine antagonist that has a high affinity for D1- and D2-like receptors. It presents a strong antagonism for several serotonin receptors, such as 5-HT2a, 5-HT2c, 5-HT6 and 5-HT7. Zotepine activities are also related to the inhibition of noradrenaline reuptake and serotonergic activity. All these effects allow zotepine to improve the negative and cognitive symptoms of schizophrenia.
Biological Half-LifeThe half-life of zotepine is reported to be of 21 hours.
Metabolism/Metabolites
Zotepine is well metabolized in the body, it actually undergoes extensive first-pass metabolism to the metabolite norzotepine and several inactive metabolites. The main enzymes involved in zotepine metabolism are CYP1A2 and CYP3A4. Some of the main metabolic pathways include N-demethylation and oxygenation of N or S atoms, hydroxylation of the aromatic ring and consecutive conjugation.
Zotepine has known human metabolites that include 2-hydroxy-zotepine, Norzotepine, Zotepine -oxide, 3-hydroxy-zotepine, and Zotepine N-oxide.
MeSH Pharmacological Classification
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