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レボメプロマジン

Levomepromazine

HCID 72287
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
60-99-1
標準SMILES
COc1ccc2c(c1)N(C[C@H](C)CN(C)C)c1ccccc1S2
InChIKey
VRQVVMDWGGWHTJ-CQSZACIVSA-N
分子式
C19H24N2OS
平均分子量
328.5 g/mol
単同位体質量
328.16093457

概要

Methotrimeprazine is a member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively. It has a role as an anticoronaviral agent, a non-narcotic analgesic, a phenothiazine antipsychotic drug, a serotonergic antagonist, a dopaminergic antagonist, a cholinergic antagonist and an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor. It is a tertiary amine and a member of phenothiazines. It derives from a hydride of a 10H-phenothiazine.

名称と識別子

優先名称
Levomepromazine
IUPAC
(2R)-3-(2-methoxyphenothiazin-10-yl)-N,N,2-trimethylpropan-1-amine
現地名
レボメプロマジン
英語名
(-)-10-(3-[Dimethylamino]-2-methylpropyl)-2-methoxy-phenothiazine maleate salt
分子式
C19H24N2OS
分子量
328.47

名称と別名

LevomepromazineMETHOTRIMEPRAZINE60-99-1LevopromeLevopromazineNeozineLevomepromazinaNirvanLevomepromazinum2-MethoxytrimeprazineNosinanSK&F 5116
名称をさらに表示
(βR)-2-メトキシ-N,N,β-トリメチル-10H-フェノチアジン-10-プロパン-1-アミン(βR)-2-メトキシ-N,N,β-トリメチル-10H-フェノチアジン-10-(1-プロパンアミン)メトトリメプラジンレボメプロマジンレボプロマジン(+)-10-[(R)-3-(ジメチルアミノ)-2-メチルプロピル]-2-メトキシ-10H-フェノチアジン(+)-2-メトキシ-10-[(R)-3-ジメチルアミノ-2-メチルプロピル]-10H-フェノチアジン(R)-3-[2-メトキシ-10H-フェノチアジン-10-イル]-N,N,2-トリメチルプロパン-1-アミン[(2R)-3-(2-メトキシ-10H-フェノチアジン-10-イル)-2-メチルプロピル]ジメチルアミンLevotominLevomepromazinXP 03rp7044C07192skf5116
RP-7044CL 36467CL 39743XP03RP 7044Bayer 1213Arc-VI-C-59G0LAW7ATQ

データベース識別子

CAS
60-99-1
PubChem CID
72287
DTXSID
DTXSID1023289
ChEMBL
CHEMBL1764
ChEBI
CHEBI:6838
UNII
9G0LAW7ATQ
EC Number
200-495-5
Nikkaji
J76.892H

物性

構造計算による物性

XLogP
4.7
極性表面積
41 Ų
水素結合供与体数
0
水素結合受容体数
4
回転可能結合数
5
重原子数
23
形式電荷
0
複雑度
378

実験および物理化学的性質

Drugs · 3 件

DEA NFLIS-Drug Category -> Depressants and Tranquilizers

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Antipsychotics

LogP4.68
Solubility5.25e-03 g/L
Human Drugs · 3 件

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Pharmaceuticals

Physical DescriptionSolid
Dissociation Constants · 2 件

9.19

9.19

Collision Cross Section176.8 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

物理化学的性質

融点
117 °C · 117°C
沸点
468 · 468.0±45.0 °C(Predicted)
比重(密度)
1.0897 · 1.0897 (rough estimate)
屈折率
1.595 · 1.5950 (estimate)
貯蔵温度
-20 °C · Store at -20°C
溶解性
Chloroform (Slightly), Methanol (Very Slightly)
外見
Solid
酸解離定数(Pka)
9.32 · 9.32±0.28(Predicted)
色
White to Off-White
水溶解度
20 mg/L · 20mg/L(25℃)
主な用途
医薬品(低分子化合物)
InChI
1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
InChIKey
VRQVVMDWGGWHTJ-CQSZACIVSA-N
SMILES
S1c2c(cc(cc2)OC)N(c3c1cccc3)C[C@@H](CN(C)C)C

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 · 4 件

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory InformationMethotrimeprazine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (100%)

毒性情報

Exposure RoutesOral; parental (intramuscular). Methotrimeprazine has an incomplete oral bioavailability, because it undergoes considerable first-pass-metabolism in the liver. Oral bioavailability is approximately 50 to 60%.
Toxicity Summary · 1 件

Methotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role. Methotrimeprazine exerts its actions through a central adrenergic-blocking, a dopamine-blocking, a serotonin-blocking, and a anticholinergic blocking.

Signs and SymptomsSymptoms of overdose include convulsions, spastic movements, and coma.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 5 件

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

LEVOMEPROMAZINE

DILI Positive

Oral,Intramuscular; Intravenous

DOI:10.1016/j.drudis.2019.09.022

安全データ

wgk
WGK 3
rtecs
SO6125000
ridadr
3249
毒性
LD50 oral in rat: 1100mg/kg
hs_code
2934302300
risk_code
20/21/22
hazard_code
Xn
safety_code
36
hazard_class
6.1(b)
packing_group
III
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

ATC Code · 3 件

N05AA02

N - Nervous system

QN - Nervous system

Pharmacodynamics · 1 件

Methotrimeprazine is a phenothiazine with pharmacological activity similar to that of both chlorpromazine and promethazine. It has the histamine-antagonist properties of the antihistamines together with central nervous system effects resembling those of chlorpromazine. (From Martindale, The Extra Pharmacopoeia, 30th ed, p604)

Mechanism of ActionMethotrimeprazine's antipsychotic effect is largely due to its antagonism of dopamine receptors in the brain. In addition, its binding to 5HT2 receptors may also play a role.
Biological Half-LifeApproximately 20 hours.
Metabolism/Metabolites · 2 件

Hepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety.

Hepatic. Methotrimeprazine is metabolized in the liver and degraded to a sulfoxid-, a glucuronid- and a demethyl-moiety. Half Life: Approximately 20 hours.

MeSH Pharmacological Classification · 3 件

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.

Absorption, Distribution and ExcretionMethotrimeprazine has an incomplete oral bioavailability, because it undergoes considerable first-pass-metabolism in the liver. Oral bioavailability is approximately 50 to 60%.
Cellular LocationsMembrane

用途と製造

Uses · 2 件

Use (kg) in Switzerland (2009): >100

For the treatment of psychosis, particular those of schizophrenia, and manic phases of bipolar disorder. As a potentiator of anesthetics: In general anesthesia where it can be used as both a pre- and post-operative sedative and analgesic. (L1857) As an anti-emetic: For the treatment of nausea and vomiting of central origin.(L1857) As a sedative: For the management of insomnia. (L1857)

Use ClassificationPharmaceuticals

上流・下流製品情報

上流原料

ナトリウムアミド

サプライヤー37 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
InvivoChem中国13549236410 · [email protected]
玺标(上海)科技有限公司18512111473 18512111473 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京世洲生物科技有限公司13675144456 · [email protected]
上海喀露蓝科技有限公司18149758185 18149758185 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
Chongqing jooe co., ltd+86-15223382610 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
陕西缔都医药化工有限公司029-029-81120477 17792793610 · [email protected]
BOC Sciences16314854226 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都标样生物科技有限公司028-81700200 13308200041 · [email protected]
上海立崎生物医学研究中心18014399201 · [email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
Xiamen Wonderful Bio Technology Co., Ltd.+86-13043004613 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
ChemeGen 中国18818260767 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
TLC梯尔希(南京)药物研发有限公司18012923235 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]
南京世洲生物科技有限公司18351873721 · [email protected]
湖北清北云研医药科技有限责任公司18162595016; 18162595016 · [email protected]

補足説明

定義ChEBI: A member of the class of phenothiazines that is 10H-phenothiazine substituted by a (2R)-3-(dimethylamino)-2-methylpropyl group and a methoxy group at positions 10 and 2 respectively.

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