エポチロンB
Epothilone B
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基本情報
- CAS
152044-54-7- 標準SMILES
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1- InChIKey
QXRSDHAAWVKZLJ-PVYNADRNSA-N- 分子式
- C27H41NO6S
- 平均分子量
- 507.7 g/mol
- 単同位体質量
- 507.26545903
概要
Epothilone B is an epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer). It has a role as an antineoplastic agent, a microtubule-stabilising agent and an apoptosis inducer. It is an epoxide and an epothilone.
名称と識別子
- 優先名称
- Epothilone B
- IUPAC
- (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
- 現地名
- エポチロンB
- 英語名
- Epothilone B
- 分子式
- C27H41NO6S
- 分子量
- 507.68
名称と別名
Epothilone BPatupilone152044-54-7(-)-Epothilone BEpo BEpothilon BEPO 906patupilonaEpithilone bEPO 906AGNF-PF-193EPO-906
名称をさらに表示
エポチロンBエポチロンB,エポチロンB (SYNTHETIC)エポチロン B(4S,7R,8S,9S,13R,14S,16S)-4,8-ジヒドロキシ-5,5,7,9,13-ペンタメチル-16-[(E)-1-メチル-2-(2-メチル-4-チアゾリル)エテニル]-13,14-エポキシ-1-オキサシクロヘキサデカン-2,6-ジオンパツピロン(-)-エポチロンB(1S,3S,7S,10R,11S,12S,16R)-7,11-ジヒドロキシ-8,8,10,12,16-ペンタメチル-3-[(1E)-1-(2-メチル-1,3-チアゾール-4-イル)プロパ-1-エン-2-イル]-4,17-ジオキサビシクロ[14.1.0]ヘプタデカン-5,9-ジオン(1S,3S,7S,10R,11S,12S,16R)-3-[(E)-1-メチル-2-(2-メチル-4-チアゾリル)エテニル]-7,11-ジヒドロキシ-8,8,10,12,16-ペンタメチル-4,17-ジオキサビシクロ[14.1.0]ヘプタデカン-5,9-ジオンEPOTHILONECS-556atupiloneEbomycin BOncology API
patupilonumDTXSID4046862UEC0H0URSEEPO906AEPO-906ACHEBI:31550(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
物性
構造計算による物性補完中
- XLogP
- 4.2
- 極性表面積
- 137 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 8
- 回転可能結合数
- 2
- 重原子数
- 35
- 形式電荷
- 0
- 複雑度
- 815
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Macrolides and lactone polyketides [PK04]
Endocrine DisruptorsPotential endocrine disrupting compound
物理化学的性質
- 融点
- 95 · 95-97°C
- 比旋光度
- 21 · D21 -35° (c = 0.7 in methanol)
- 沸点
- 680.2 · 680.2±55.0 °C(Predicted)
- 比重(密度)
- 1.136 · 1.136
- 貯蔵温度
- -20 °C · Store at -20°C
- 溶解性
- DMSO (最大 40mg/ml) またはエタノール (最大 35mg/ml) に可溶。
- 外見
- 白からオフホワイトの固体
- 酸解離定数(Pka)
- 13.57 · 13.57±0.70(Predicted)
- 色
- 無色
- 由来生物
- Sorangium cellulosum
- 安定性
- 2 · 購入日から2年間安定です。この DMSO またはエタノール溶液は、-20°C で 1 か月間保存できます。
- InChIKey
- QXRSDHAAWVKZLJ-PVYNADRNSA-N
- SMILES
- [C@]12([H])[C@](C)(O1)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@H](/C(/C)=C/C1=CSC(C)=N1)C2
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
Danger
H300 (75%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 1 (75%)
安全データ
- wgk
- 3
- hs_code
- 29419090
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Mechanism of Action
The principal mechanism of the epothilone class is inhibition of microtubule function. Microtubules are essential to cell division, and epothilones therefore stop cells from properly dividing. Epothilone B possess the same biological effects as taxol both in vitro and in cultured cells. This is because they share the same binding site, as well as binding affinity to the microtubule. Like taxol, epothilone B binds to the αβ-tubulin heterodimer subunit. Once bound, the rate of αβ-tubulin dissociation decreases, thus stabilizing the microtubules. Furthermore, epothilone B has also been shown to induce tubulin polymerization into microtubules without the presence of GTP. This is caused by formation of microtubule bundles throughout the cytoplasm. Finally, epothilone B also causes cell cycle arrest at the G2-M transition phase, thus leading to cytotoxicity and eventually cell apoptosis.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
応用分野
天然物の起源粘液細菌Sorangium cellulosum
使用Epothilones are polyketide natural products that inhibit cancer cells by a mechanism similar to paclitaxel, and also are effective against paclitaxel-resistant tumours. Epothilone B is what is known as a microtubule stabilizer. When a cell divides, the chromosomes that will end up in each cell are separated by thin filaments called microtubules. Normally these microtubules then break down as the cell division progresses. This class of cytotoxic chemo drugs prevents that break down and thus prevents cells from completing division.
一般的な説明Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).
上流・下流製品情報
上流原料
関連反応
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化合物ノート
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