リダホロリムス
Ridaforolimus
基本情報
- CAS
572924-54-0- 標準SMILES
CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](OP(C)(C)=O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C- InChIKey
BUROJSBIWGDYCN-GAUTUEMISA-N- 分子式
- C53H84NO14P
- 平均分子量
- 990.2 g/mol
- 単同位体質量
- 989.56294335
概要
Ridaforolimus is a small molecule and non-prodrug analogue of the lipophilic macrolide antibiotic rapamycin with potential antitumor activity. Ridaforolimus binds to and inhibits the mammalian target of rapamycin (mTOR), which may result in cell cycle arrest and, consequently, the inhibition of tumor cell growth and proliferation. Upregulated in some tumors, mTOR is a serine/threonine kinase involved in regulating cellular proliferation, motility, and survival that is located downstream of the PI3K/Akt signaling pathway.
名称と識別子
- 優先名称
- Ridaforolimus
- IUPAC
- (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-12-[(2R)-1-[(1S,3R,4R)-4-dimethylphosphoryloxy-3-methoxycyclohexyl]propan-2-yl]-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone
- 現地名
- リダホロリムス
- 英語名
- 42-(Dimethylphosphinate)rapamycin
- 分子式
- C53H84NO14P
- 分子量
- 990.21
名称と別名
RidaforolimusDeforolimus572924-54-0AP23573MK-8669AP-23573MK866948Z35KB15KDTXSID001025942Rapamycin, 42-(dimethylphosphinate)ridaforolimusumMK 8669
名称をさらに表示
リダホロリムスリダホロリムス (JAN)デホロリムスラパマイシン42-(ジメチルホスフィン酸)(1R,2R,4S)-4-[(2R)-2-[(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-ジヒドロキシ-19,30-ジメトキシ-15,17,21,23,29,35-ヘキサメチル-2,3,10,14,20-ペンタオキソ-11,36-ジオキサ-4-アザトリシクロ[30.3.1.04,9]ヘキサトリアコンタ-16,24,26,28-テトラエン-12-イル]プロピル]-2-メトキシシクロヘキシル ジメチルホスフィナートDeforoliMus APIRidaforolimus, >RidaforoliMus, >80%DeforoliMus(MK-8669)Deforolimus (AP23573)deforolimus 572924-54-0Ridaforolimus (MK-8669)Deforolimus (AP23573)42-
(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-12-[(2R)-1-[(1S,3R,4R)-4-dimethylphosphoryloxy-3-methoxycyclohexyl]propan-2-yl]-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentoneCHEBI:82677(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-12-((2R)-1-((1S,3R,4R)-4-dimethylphosphoryloxy-3-methoxycyclohexyl)propan-2-yl)-1,18-dihydroxy-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo(30.3.1.04,9)hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentoneRefChem:179414L01XE19DTXCID401510193682-462-9Taltorvic
物性
構造計算による物性
- XLogP
- 5.9
- 極性表面積
- 202 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 14
- 回転可能結合数
- 8
- 重原子数
- 69
- 形式電荷
- 0
- 複雑度
- 1,940
物理化学的性質
- 融点
- 95 · 95-98°C
- 沸点
- 996.2 · 996.2±75.0 °C(Predicted)
- 比重(密度)
- 1.18 · 1.18±0.1 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- 溶解性
- DMSO（微量）、メタノール（微量）
- 外見
- 個体
- 酸解離定数(Pka)
- 10.4 · 10.40±0.70(Predicted)
- 色
- オフホワイトからペールイエロー
- 安定性
- 吸湿性
- InChIKey
- BUROJSBIWGDYCN-GAUTUEMISA-N
化学的性質
化学的特性Off-White Solid
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
H361 (14.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
P203, P260, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 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
Hazard Classes and CategoriesRepr. 2 (14.3%)
安全データ
- wgk
- WGK 3
- Hazard Classifications
- STOT RE 2
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Mechanism of Action
Deforolimus inhibits the mammalian target of rapamycin (mTOR), a serine kinase of the phosphatidylinositol-3-kinase (PI3K) family that regulates protein synthesis, affecting cell growth and proliferation. mTOR is a downstream effector of the phosphatidylinositol 3-kinase/Akt and nutrient-sensing pathways which cancer cells need to proliferate.
応用分野
説明MK-8669 is a rapamycin analog that selectively inhibits mTOR (IC50 = 0.2 nM). Like rapamycin, MK-8669 binds FKBP12 to form a complex that associates with the FKBP-rapamycin binding domain on mTOR and allosterically inhibits mTORC1 kinase activity. MK-8669 is more water soluble than rapamycin and is amenable to oral or intravenous administration. Formulations containing rapalogs, including MK-8669, have promise against a subset of cancers, including advanced kidney cancer. MK-8669 is also being examined for effectiveness against cancers when used in combination with other chemotherapeutic compounds.
上流・下流製品情報
上流原料
補足説明
ChEBI: A semisynthetic derivative that is sirolimus in which hydroxy group attached to the cyclohexyl moiety has been converted to the corresponding dimethylphosphinate.
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