CAS 912999-49-6 Onalespib (HCID 11955716)

基本情報

CAS: 912999-49-6
標準SMILES: CC(C)c1cc(C(=O)N2Cc3ccc(CN4CCN(C)CC4)cc3C2)c(O)cc1O
InChIKey: IFRGXKKQHBVPCQ-UHFFFAOYSA-N
分子式: C24H31N3O3
平均分子量: 409.5 g/mol
単同位体質量: 409.23654185

概要

Onalespib is a member of the class of isoindoles that is isoindole in which the amino group has been acylated by a 2,4-dihydroxy-5-isopropylbenzoyl group and in which position 5 of the isoidole moiety has been substituted by a (4-methylpiperazin-1-yl)methyl group. A second-generation Hsp90 inhibitor. It has a role as an antineoplastic agent and a Hsp90 inhibitor. It is a tertiary carboxamide, a member of benzamides, a member of isoindoles, a member of resorcinols and a N-alkylpiperazine.

名称と識別子

優先名称: Onalespib
IUPAC: (2,4-dihydroxy-5-propan-2-ylphenyl)-[5-[(4-methylpiperazin-1-yl)methyl]-1,3-dihydroisoindol-2-yl]methanone
現地名: オナレスピブ
英語名: Onalespib
分子式: C24H31N3O3
分子量: 409.52

名称と別名

Onalespib912999-49-6AT13387AT-13387AT 13387onalespibumQ7Y33N57ZZATI13387XATI-13387X(2,4-Dihydroxy-5-isopropylphenyl)-(5-(4-methylpiperazin-1-ylmethyl)-1,3-dihydroisoindol-2-yl)methanoneCHEBI:140592DTXSID80238485

名称をさらに表示

オナレスピブ4-{5-[(4-メチルピペラジン-1-イル)メチル]-2,3-ジヒドロ-1H-イソインドール-2-カルボニル}-6-(プロパン-2-イル)ベンゼン-1,3-ジオールα-[5-(4-メチルピペラジノメチル)イソインドリン-2-イル]-2,4-ジヒドロキシ-5-イソプロピルベンズアルデヒド4-[5-(4-メチルピペラジノメチル)イソインドリン-2-イルカルボニル]-6-イソプロピルレソルシノールCS-1866ATI-13387AT13387, >=98%Onalespib LactateAT13387(Onalespib)ATI-13387

Methanone, (1,3-dihydro-5-((4-methyl-1-piperazinyl)methyl)-2H-isoindol-2-yl)(2,4-dihydroxy-5-(1-methylethyl)phenyl)-4-{5-[(4-methylpiperazin-1-yl)methyl]-2,3-dihydro-1H-isoindole-2-carbonyl}-6-(propan-2-yl)benzene-1,3-diol4-(5-((4-methylpiperazin-1-yl)methyl)-2,3-dihydro-1H-isoindole-2-carbonyl)-6-(propan-2-yl)benzene-1,3-diolRefChem:856776DTXCID00160976Onalespib (AT13387)(2,4-Dihydroxy-5-isopropylphenyl)(5-((4-methylpiperazin-1-yl)methyl)isoindolin-2-yl)methanone912999-49-6 (free base)

物性

構造計算による物性

XLogP: 3.1
極性表面積: 67.3 Å²
水素結合供与体数: 2
水素結合受容体数: 5
回転可能結合数: 4
重原子数: 30
形式電荷: 0
複雑度: 592

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LogP2.87

物理化学的性質

沸点: 605.7 · 605.7±55.0 °C(Predicted)
比重(密度): 1.237 · 1.237
貯蔵温度: -20 °C · Store at -20°C
溶解性: 2 O; · insoluble in H2O; ≥13.25 mg/mL in DMSO; ≥47.7 mg/mL in EtOH with ultrasonic
外見: solid
酸解離定数(Pka): 8.5 · 8.50±0.48(Predicted)
色: White to off-white
InChI: InChI=1S/C24H31N3O3/c1-16(2)20-11-21(23(29)12-22(20)28)24(30)27-14-18-5-4-17(10-19(18)15-27)13-26-8-6-25(3)7-9-26/h4-5,10-12,16,28-29H,6-9,13-15H2,1-3H3
InChIKey: IFRGXKKQHBVPCQ-UHFFFAOYSA-N
SMILES: C(N1CC2=C(C1)C=CC(CN1CCN(C)CC1)=C2)(C1=CC(C(C)C)=C(O)C=C1O)=O

安全と法規制

安全データ

注意喚起語: 警告
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

化学と産業

応用分野 · 1 件

説明Onalespib, also known as AT13387, is a selective inhibitor of Hsp90 (IC50 = 18 nM). It induces the degradation of specific Hsp90 client proteins, including mutant EGFR, for up to seven days in tumor cell lines in vitro and up to three days in vivo. Onalespib is retained in tumor xenografts and is efficacious in a range of xenograft models. It differs from other HSP90 inhibitors in its longer duration of target inhibition and its favorable toxicity profile in phase I studies in patients with refractory solid tumors.