基本情報
- CAS
29767-20-2- 標準SMILES
COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5COC(c6cccs6)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O- InChIKey
NRUKOCRGYNPUPR-PSZSYXFXSA-N- 分子式
- C32H32O13S
- 平均分子量
- 656.7 g/mol
- 単同位体質量
- 656.15636224
概要
Teniposide is a furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding. It has a role as an antineoplastic agent and an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor. It is a beta-D-glucoside, a member of thiophenes, a member of phenols, an aromatic ether, a gamma-lactone, a furonaphthodioxole, a cyclic acetal and a monosaccharide derivative. It is functionally related to a podophyllotoxin.
名称と識別子
- 優先名称
- Teniposidum
- IUPAC
- (5S,5aR,8aR,9R)-5-[[(4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
- 現地名
- テニポシド
- 英語名
- Teniposide
- 分子式
- C32H32O13S
- 分子量
- 656.65
名称と別名
TeniposidumRefChem:1048736(5S,5aR,8aR,9R)-5-(((4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-thiophen-2-yl-4,4a,6,7,8,8a-hexahydropyrano(3,2-d)(1,3)dioxin-6-yl)oxy)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-(2)benzofuro(6,5-f)(1,3)benzodioxol-8-oneTeniposidum [INN-Latin]Teniposido [INN-Spanish]SCHEMBL94844(5R,5aR,8aR,9S)-9-(((4aR,6R,7R,8R,8aS)-7,8-dihydroxy-2-(thiophen-2-yl)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one(5S,5aR,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5,5a,6,8,8a,9-hexahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl 4,6-O-(2-thienylmethylene)-beta-D-glucopyranosideFuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-[[4,6-O-(2-thienylmethylene)-.beta.-D-glucopyranosyl]oxy]-, (5R,5aR,8aR,9S)-(5R,5aα)-5,8,8aβ,9β-テトラヒドロ-5-(4-ヒドロキシ-3,5-ジメトキシフェニル)-9-[[4-O,6-O-[(R)-2-チエニルメチレン]-β-D-グルコピラノシル]オキシ]フロ[3',4':6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aH)-オンテニポシド4'-デメチルエピポドフィロトキシン-9-(4,6-O-2-テニリデンβ-D-グルコピラノシド)
名称をさらに表示
ブモン(5R,5aα)-5,8,8aβ,9β-テトラヒドロ-5-(4-ヒドロキシ-3,5-ジメトキシフェニル)-9-[[4-O,6-O-[(R)-2-チエニルメチレン]-β-D-グルコピラノシル]オキシ]フロ[3′,4′:6,7]ナフト[2,3-d]-1,3-ジオキソール-6(5aH)-オン4′-デメチルエピポドフィロトキシン-9-(4,6-O-2-テニリデンβ-D-グルコピラノシド)(10R,11R,15R,16S)-16-{[(2R,4aR,6R,7R,8R,8aS)-7,8-ジヒドロキシ-2-(チオフェン-2-イル)-ヘキサヒドロ-2H-ピラノ[3,2-d][1,3]ジオキシン-6-イル]オキシ}-10-(4-ヒドロキシ-3,5-ジメトキシフェニル)-4,6,13-トリオキサテトラシクロ[7.7.0.03,7.011,15]ヘキサデカ-1,3(7),8-トリエン-12-オンetpvehemvm-26VumonEniposidensc122819TeniposidTenoposidensc-122819TENIPOSIDE
データベース識別子
- CAS
29767-20-2- PubChem CID
- 34698
- ChEBI
CHEBI:75988- Nikkaji
- J59.196C
物性
構造計算による物性
- XLogP
- 1.2
- 極性表面積
- 189 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 14
- 回転可能結合数
- 6
- 重原子数
- 46
- 形式電荷
- 0
- 複雑度
- 1,090
実験および物理化学的性質
LogP1.5
Solubility5.98e-02 g/L
Physical DescriptionSolid
物理化学的性質
- 融点
- 244 · 244-247°C
- 比旋光度
- 20 · D20 -107° (9:1 chloroform/methanol)
- 沸点
- 650.86 °C · 650.86°C (rough estimate)
- 比重(密度)
- 1.2568 · 1.2568 (rough estimate)
- 屈折率
- 1.553 · 1.5530 (estimate)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- 10 mg/mL、透明 · DMSO：可溶10mg/mL、透明
- 酸解離定数(Pka)
- 10.13 · 10.13(at 25℃)
- 外見
- 粉
- 色
- 白からベージュ
- Merck
- 14 · 14,9145
- 安定性
- 吸湿性
- InChIKey
- NRUKOCRGYNPUPR-QBPJDGROSA-N
- SMILES
- [s]1c(ccc1)[C@H]2O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O[C@H]4[C@@H]5[C@@H]([C@@H](c7c4cc8c(c7)OCO8)c6cc(c(c(c6)OC)O)OC)C(=O)OC5)CO2
- CAS データベース
- 29767 · 29767-20-2(CAS DataBase Reference)
化学的性質
化学的特性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。
毒性情報
Toxicity Summary
The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. Teniposide binds to and inhibits DNA topoisomerase II. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate.
Carcinogen Classification2A, probably carcinogenic to humans. (L135)
安全データ
- wgk
- 3
- rtecs
- KC0180000
- ridadr
- UN 2811 6.1 / PGIII
- 毒性
- LD50 intraperitoneal in mouse: 29570ug/kg
- hs_code
- 29349990
- risk_code
- 36/37/38-45
- hazard_code
- Xi,T
- safety_code
- 26-36-45-53
- Hazard Classifications
- Carc. 1B
- ストレージクラス
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- 有毒物質データの
- 29767-20-2(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/MetabolitesRoute of Elimination: From 4% to 12% of a dose is excreted in urine as parent drug. Fecal excretion of radioactivity within 72 hours after dosing accounted for 0% to 10% of the dose.
Half Life: 5 hours
Cellular LocationsCytoplasm
Metabolite PathwaysTeniposide Action Pathway
用途と製造
UsesTeniposide is used for the treatment of refractory acute lymphoblastic leukaemia
応用分野
用途DNAトポイソメラーゼIIの阻害剤、抗悪性腫瘍剤
使用Teniposide is a podophyllotoxin derivative that causes dose-dependent single- and double-stranded breaks in DNA by inhibiting topoisomerase II. Its cytostatic effects are related to its ability to stabilize the DNA-topoisomerase II complex during DNA replication, inducing DNA damage and cellular apoptosis. Teniposide has been widely used in the treatment of various cancers including, small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia.
一般的な説明Teniposide is available in 50-mg ampules with Cremophor ELfor IV administration in the treatment of acute lymphoblasticleukemia (ALL). The agent is more potent as an inhibitor oftopoisomerase II. The pharmacokinetics of teniposide issimilar to that of etoposide; however, the more lipophilic teniposideis more highly protein bound (99%) and less isexcreted unchanged in the urine (10%–20%). There is alsogreater overall metabolism of teniposide; however, CYP3A4-mediated conversion to the active catechol is slower comparedwith etoposide. Elimination occurs primarily in the urine witha terminal elimination half-life of 5 hours.
上流・下流製品情報
上流原料
サプライヤー100 社
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
中梦研（湖北）科技有限公司0717-6300888 18062399888 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017-8007 17602929471
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
湖南瑞威尔生物科技有限公司15608648206 13297919155 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [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]
上海恩诺生物科技有限公司+86 (21) 6435-5022
Advanced chemblocks inc650-6922368 650-6922368;650-6922368 · [email protected]
InvivoChem中国13549236410 · [email protected]
MedBio脉铂医药021-69568360 18916172912 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
杭州璟皓生物科技有限公司（原河南辛迪加生物）17513242016 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
上海瀚香生物科技有限公司177-54423994 17754423994 · [email protected]
ChemeGen 中国18818260767 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
武汉海正工贸发展有限公司027-8866 0053/88660577/88660578
上海思域化工科技有限公司86-21-34053660 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
苏州亚科科技股份有限公司0512-87182055 13451648594 · [email protected]
上海汇凯化学科技有限公司021-61995394 18916691159 · [email protected]
Cato Research Chemicals Inc.020-81960175 · [email protected]
上海湄水化工科技有限公司021-60549325 18616193163
雷丁试剂0510-85629785 18013409632 · [email protected]
湖南华腾制药有限公司400-8592883 15367835770 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
TargetMol中国（陶术生物）021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
北京秦岭医药科技有限公司010-61241352 18901327973 · [email protected]
资川生化科技(苏州)有限公司0512-66317708 13372112871 · [email protected]
上海谱振生物科技有限公司4001650900 13817534909 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
BOC Sciences16314854226 · [email protected]
药渡经纬信息科技(北京)有限公司+86-400-851-9921 · [email protected]
上海炎泽化工有限公司15345144255 19901447308 · [email protected]
補足説明
定義ChEBI: A furonaphthodioxole that is a synthetic derivative of podophyllotoxin with anti-tumour activity; causes single- and double-stranded breaks in DNA and DNA-protein cross-links and prevents repair by topoisomerase II binding.
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