ビンデシン
methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
基本情報
- CAS
53643-48-4- 標準SMILES
CC[C@]1(O)C[C@@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(N)=O)[C@H](O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1- InChIKey
HHJUWIANJFBDHT-ZVTSDNJWSA-N- 分子式
- C43H55N5O7
- 平均分子量
- 753.9 g/mol
- 単同位体質量
- 753.41014911
概要
Vinblastine derivative with antineoplastic activity against cancer. Major side effects are myelosuppression and neurotoxicity. Vindesine is used extensively in chemotherapy protocols (antineoplastic combined chemotherapy protocols).
名称と識別子
- 優先名称
- methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
- IUPAC
- methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
- 現地名
- ビンデシン
- 英語名
- Desacetylvinblastineamide
- 分子式
- C43H55N5O7
- 分子量
- 753.93
名称と別名
methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylateVincaleukoblastine, 23-amino-O(sup 4)-deacetyl-23-demethoxy-methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraene-13-carboxylateR-VindesineVINDESINE [INN]VINDESINE [MI]VINDESINE [HSDB]VINDESINE [USAN]Vindesinum [INN-Latin]UNII-RSA8KO39WHVindesina [INN-Spanish]VINDESINE [VANDF]
名称をさらに表示
物性
構造計算による物性
- XLogP
- 2.7
- 極性表面積
- 165 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 10
- 回転可能結合数
- 7
- 重原子数
- 55
- 形式電荷
- 0
- 複雑度
- 1,570
実験および物理化学的性質
Melting Point230-232 °C
物理化学的性質
- 融点
- 230 · 230-232°
- 比旋光度
- 25 · D25 +39.4° (c = 1.0 in methanol)
- 比重(密度)
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- 酸解離定数(Pka)
- pKa (DMF 66%) 5.39, 7.36; (H2O) 6.04, 7.67(at 25℃)
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。
安全データ
- ridadr
- 1544
- hazard_class
- 6.1(a)
- packing_group
- II
- 有毒物質データの
- 53643-48-4(Hazardous Substances Data)
化学と産業
薬理情報
Protein Binding65-75%
Pharmacodynamics
Vindesine is indicated for the treatment of acute lymphocytic leukemia of childhood that is resistant to vincristine and non-oat cell lung cancer. Vindesine causes the arrest of cells in metaphase mitosis. It is three times more potent than vincristine and nearly 10 times more potent than vinblastine in causing mitotic arrest in <i>in vitro</i> studies at doses designed to arrest from 10 to 15% of the cells in mitosis. Vindesine and vincristine are approximately equipotent at dose levels that arrest 40 to 50% of the cells in mitosis. Unlike vinblastine, vindesine produces very few postmetaphase cells. Vindesine has demonstrated activity in patients who have relapsed while receiving multiple-agent treatment that included vincristine.
Mechanism of ActionVindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. The drug is cell-cycle specific for the S phase.
Biological Half-Life24 hours.
Metabolism/MetabolitesHepatic
応用分野
使用Antineoplastic.
上流・下流製品情報
上流原料
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