ブレクスピプラゾール

ブレクスピプラゾール 化学構造式
913611-97-9
CAS番号.
913611-97-9
化学名:
ブレクスピプラゾール
别名:
7-(4-(4-(ベンゾ[B]チオフェン-4-イル)ピペラジン-1-イル)ブトキシ)キノリン-2(1H)-オン;ブレクスピプラゾール;ブレクスピプラゾール (JAN);レキサルティ;ブレキスピプラゾール;7-{4-[4-(1-ベンゾチオフェン-4-イル)ピペラジン-1-イル]ブトキシ}-1,2-ジヒドロキノリン-2-オン;7-[4-[4-(ベンゾ[b]チオフェン-4-イル)-1-ピペラジニル]ブトキシ]キノリン-2(1H)-オン;7-[4-[4-(ベンゾ[b]チオフェン-4-イル)ピペラジン-1-イル]ブトキシ]キノリン-2(1H)-オン
英語名:
Brexpiprazole
英語别名:
OPC-34712;Brexpiprazole impurity a;7-[4-(4-(Benzo[b]thien-4-yl)-piperazin-1-yl)butoxy]-1H-quinolin-2-one;7-{4-[4-(1-Benzothiophen-4-yl)piperazin-1-yl]butoxy}quinolin-2(1H)-one;7-(4-(4-(Benzo[b]thiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1H)-one;CS-1678;ipiprazole;Epiprazole;Brexpiprazole;Brexipiprazole
CBNumber:
CB52681994
化学式:
C25H27N3O2S
分子量:
433.57
MOL File:
913611-97-9.mol

ブレクスピプラゾール 物理性質

融点 :
179 - 181oC
沸点 :
675.2±55.0 °C(Predicted)
比重(密度) :
1.245±0.06 g/cm3(Predicted)
貯蔵温度 :
Refrigerator
溶解性:
ジクロロメタン(微量)、クロロホルム(微量)、メタノール(微量)
酸解離定数(Pka):
11.22±0.70(Predicted)
外見 :
個体
色:
ホワイトからオフホワイト
InChI:
InChI=1S/C25H27N3O2S/c29-25-9-7-19-6-8-20(18-22(19)26-25)30-16-2-1-11-27-12-14-28(15-13-27)23-4-3-5-24-21(23)10-17-31-24/h3-10,17-18H,1-2,11-16H2,(H,26,29)
InChIKey:
ZKIAIYBUSXZPLP-UHFFFAOYSA-N
SMILES:
N1C2=C(C=CC(OCCCCN3CCN(C4=C5C=CSC5=CC=C4)CC3)=C2)C=CC1=O
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
絵表示(GHS) GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
注意喚起語
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 GHS hazard pictograms P264, P270, P301+P312, P330, P501
H351 発がんのおそれの疑い 発がん性 2 警告 P201, P202, P281, P308+P313, P405,P501
H360 生殖能または胎児への悪影響のおそれ 生殖毒性 1A, 1B 危険 GHS hazard pictograms
H362 授乳中の子に害を及ぼすおそれ 生殖毒性、授乳に対するまたは 授乳を介したの影響 追加区分 P201, P260, P263, P264, P270,P308+P313
H372 長期にわたる、または反復暴露により臓器の障 害 特定標的臓器有害性、単回暴露 1 危険 GHS hazard pictograms P260, P264, P270, P314, P501
H400 水生生物に強い毒性 水生環境有害性、急性毒性 1 警告 GHS hazard pictograms P273, P391, P501
H410 長期的影響により水生生物に非常に強い毒性 水生環境有害性、慢性毒性 1 警告 GHS hazard pictograms P273, P391, P501
注意書き
P201 使用前に取扱説明書を入手すること。
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
P260 粉じん/煙/ガス/ミスト/蒸気/スプレーを吸入しないこ と。
P263 妊娠中/授乳期中は接触を避けること。
P264 取扱い後は皮膚をよく洗うこと。
P264 取扱い後は手や顔をよく洗うこと。
P270 この製品を使用する時に、飲食または喫煙をしないこ と。
P273 環境への放出を避けること。
P281 指定された個人用保護具を使用すること。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P314 気分が悪い時は、医師の診断/手当てを受けること。
P405 施錠して保管すること。
P501 内容物/容器を...に廃棄すること。

ブレクスピプラゾール 価格 もっと(1)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01COBQJ-9589
Brexpiprazole
913611-97-9 100mg ¥176400 2018-12-26 購入

ブレクスピプラゾール 化学特性,用途語,生産方法

効能

統合失調症治療薬

商品名

レキサルティ (大塚製薬)

説明

Brexpiprazole is a novel antipsychotic drug which serves as a serotonin ® dopamine activity modulator and has demonstrated efficacy as an adjunctive treatment in patients with major depressive disorder (MDD). The drug exhibits a unique pharmacological profile, acting as a partial agonist of serotonin 5-HT1A and dopamine D2 receptors and as a full antagonist of 5-HT2A and noradrenaline α1B/2C receptors, with similar subnanomolar binding affinity. The drug, which was developed by Otsuka and Lundbeck, was approved in 2015 by the FDA for the treatment of schizophrenia and as an adjunctive treatment for depression. Brexpiprazole is widely considered to be a successor to Otsuka’s antipsychotic drug aripiprazole (trade name Abilify) whose patent expired in August 2014.

使用

Brexpiprazole is a kind of atypical antipsychotic. It is a dopamine D2 receptor partial agonist. As a novel serotonin-dopamine activity modulator, it can be used for the treatment of schizophrenia, and for the adjunctive treatment for depression. It can also provide efficacy and tolerability over established adjunctive treatments formajor depressive disorder(MDD).Recent study has also suggested it can ameliorate PCP-induced cognitive deficits in mice via 5-HT1A receptors.

定義

ChEBI: Brexpiprazole(913611-97-9) is a N-arylpiperazine. It is a novel D2 dopamine and serotonin 1A partial agonist, called serotonin-dopamine activity modulator (SDAM), and a potent antagonist of serotonin 2A receptors, noradrenergic alpha 1B and 2C receptors. Brexpiprazole is a drug candidate useful in treatment and prevention of mental disorders including CNS disorders.

合成

Commercially available fluorobenzaldehyde (60) underwent a substitution reaction with commercial tert-butyl piperazine-1- carboxylate (61) under basic conditions to afford the piperazinyl benzaldehyde 62 in excellent yield. Next, the construction of the benzothiophene was affected by initial condensation of thioglycolic acid ethyl ester 63 with ochlorobenzaldehyde 62 under mildly basic conditions at elevated temperatures. Treatment with aqueous base and adjustment of pH to roughly 5 through the use of 4 N HCl furnished the 2-carboxylic acid benzothiophene 64 in 80% yield across the three-step operation. Next, decarboxylation through the use of cuprous oxide using conditions slightly modified from those originally described by Goosen followed by acidic removal of the Boc protecting group on the terminal piperazine nitrogen secured the key piperazinyl benzothiophene subunit 65 as the corresponding hydrochloride salt.
The hydroxyquinolone and linker component synthesis began with alkylation of commercially available quinolone 66 with 1,4-bromochlorobutane (67) under basic conditions to furnish chloroalkoxyquinolone 68. A subsequent alkylation with hydrochloride salt 65 using potassium carbonate and warm aqueous ethanol followed by recrystallizative workup resulted in clean conversion to brexpiprazole (VIII) in 78% yield from 68.

説明図

酵素阻害剤

This serotonin-dopamine activity modulator, or SDAM (FW = 433.60 g/mol; CAS 913611-97-9), also known as OPC-34712, Rexulti, 7-{4-[4-(1- benzothiophen-4-yl)piperazin-1-yl]butoxy}quinolin-2(1H)-one, is an atypical antipsychotic drug that acts as a dopamine D2L (Ki = 1.1 nM) and D3 (Ki = 0.3 nM) receptor partial agonist and a partial agonist of 5-HT1A receptors (Ki = 0.12 nM). Brexpiprazole is also an antagonist of the 5-HT2A (Ki = 0.47 nM), 5-HT2B (Ki = 1.9 nM), 5-HT7 (Ki = nM), α1B-adrenergic (Ki = 0.17 nM), α2C-adrenergic (Ki = 0.59 nM), and histamine H1 receptors (Ki = 19 nM). It has negligible affinity for the mACh receptors. Rexulti is an FDA-approved add-on medication for major depressive disorder in adults. See Aripiprazole

Mode of action

Brexpiprazole's suggested mechanism of action is based on its impact on dopamine and serotonin receptors. As a serotonin-dopamine activity modulator (SDAM), it acts as a novel partial agonist for D2 dopamine and serotonin 1A receptors while effectively blocking the serotonin 2A receptors, as well as noradrenergic alpha 1B and 2C receptors.

参考文献

https://en.wikipedia.org/wiki/Brexpiprazole
https://www.drugbank.ca/drugs/DB09128
Maeda, K, et al. "Brexpiprazole I: in vitro and in vivo characterization of a novel serotonin-dopamine activity modulator." Journal of Pharmacology & Experimental Therapeutics 350.3(2014):589-604.
Maeda, K, et al. "Brexpiprazole II: antipsychotic-like and procognitive effects of a novel serotonin-dopamine activity modulator." Journal of Pharmacology & Experimental Therapeutics 350.3(2014):605.
Yoshimi, N, et al. "Effects of brexpiprazole, a novel serotonin-dopamine activity modulator, on phencyclidine-induced cognitive deficits in mice: a role for serotonin 5-HT1A receptors. " Pharmacology Biochemistry & Behavior 124(2014):245.

ブレクスピプラゾール 上流と下流の製品情報

原材料

準備製品


ブレクスピプラゾール 生産企業

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ブレクスピプラゾール  スペクトルデータ(1HNMR)


913611-97-9(ブレクスピプラゾール)キーワード:


  • 913611-97-9
  • Brexpiprazole
  • 7-[4-(4-benzo[b]thien-4-yl-1-piperazinyl)butoxy]- 2(1H)-Quinolinone
  • 7-[4-[4-(1-Benzothiophen-4-yl)piperazin-1-yl]butoxy]-1H-quinolin-2-one
  • CS-1678
  • OPC 34712; OPC34712; OPC-34712
  • Brexpiprazole(OPC34712)
  • OPC-34712;OPC34712
  • 2(1H)-Quinolinone, 7-[4-(4-benzo[b]thien-4-yl-1-piperazinyl)butoxy]-
  • Epipiprazole Impurities
  • Epipiprazole863
  • Epipiprazole864
  • Epipiprazole860
  • Impurities of Epipiprazole1
  • BrexpiprazoleQ: What is Brexpiprazole Q: What is the CAS Number of Brexpiprazole Q: What is the storage condition of Brexpiprazole
  • TIANFU CHEM---Brexpiprazole
  • 7-(4-(4-(Benzo[b]thiophen-4-yl)piperazin-1-yl)butoxy)quinolin-2(1H)-one
  • Brexpiprazole impurity a
  • 7-{4-[4-(1-Benzothiophen-4-yl)piperazin-1-yl]butoxy}quinolin-2(1H)-one
  • OPC-34712
  • 7-[4-(4-(Benzo[b]thien-4-yl)-piperazin-1-yl)butoxy]-1H-quinolin-2-one
  • 7-[4-[4-(4-Benzothienyl)-1-piperazinyl]butoxy]quinolin-2(1H)-one
  • Brexpiprazole Crude
  • Brexpiprazole 7-[4-(4-Benzo[b]thien-4-yl-1-piperazinyl)butoxy]-2(1H)- quinolinone
  • ipiprazole
  • Epiprazole
  • Brexipiprazole
  • 7-(4-(4-(ベンゾ[B]チオフェン-4-イル)ピペラジン-1-イル)ブトキシ)キノリン-2(1H)-オン
  • ブレクスピプラゾール
  • ブレクスピプラゾール (JAN)
  • レキサルティ
  • ブレキスピプラゾール
  • 7-{4-[4-(1-ベンゾチオフェン-4-イル)ピペラジン-1-イル]ブトキシ}-1,2-ジヒドロキノリン-2-オン
  • 7-[4-[4-(ベンゾ[b]チオフェン-4-イル)-1-ピペラジニル]ブトキシ]キノリン-2(1H)-オン
  • 7-[4-[4-(ベンゾ[b]チオフェン-4-イル)ピペラジン-1-イル]ブトキシ]キノリン-2(1H)-オン
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