methyl (13S,15S,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

• ChemBase编号: 194
• 分子式: C43H55N5O7
• 平均质量: 753.9261
• 单一同位素质量: 753.41014913
• SMILES: O[C@]1([C@@H]2N(c3c([C@@]42[C@H]2N(CC4)CC=C[C@]2([C@H]1O)CC)cc(c(OC)c3)[C@]1(C[C@H]2C[C@](O)(CN(C2)CCc2c1[nH]c1c2cccc1)CC)C(=O)OC)C)C(=O)N
• Canonical SMILES: COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@@H]2CN(CCc5c1[nH]c1c5cccc1)C[C@](C2)(O)CC)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)N)O)(CC)C=CC1
• InChI: InChI=1S/C43H55N5O7/c1-6-39(52)21-25-22-42(38(51)55-5,33-27(13-17-47(23-25)24-39)26-11-8-9-12-30(26)45-33)29-19-28-31(20-32(29)54-4)46(3)35-41(28)15-18-48-16-10-14-40(7-2,34(41)48)36(49)43(35,53)37(44)50/h8-12,14,19-20,25,34-36,45,49,52-53H,6-7,13,15-18,21-24H2,1-5H3,(H2,44,50)/t25-,34+,35-,36-,39+,40-,41-,42+,43+/m1/s1
• InChIKey: HHJUWIANJFBDHT-KOTLKJBCSA-N

名称和登记号

名称

• IUPAC标准名: methyl (13S,15S,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,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^4,^1^2.0^5,^1^0]nonadeca-4(12),5,7,9-tetraene-13-carboxylate; methyl (13S,15S,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(7),3,5,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
• IUPAC传统名: vindesine; DVA
• 商标名: DAVA; Eldesine; Eldisine
• 别名: Vindesine Sulfate; Desacetylvinblastine Amide Sulfate; Vindesine

登记号

• CAS号: 59917-39-4
• PubChem SID: 46504548; 160963657
• PubChem CID: 40839
• CHEBI ID: 36373
• ATC码: L01CA03
• CHEMBL: 219146
• Chemspider ID: 37302
• DrugBank ID: DB00309
• KEGG ID: D01769
• 美国药典/FDA物质标识码: RSA8KO39WH
• 维基百科标题: Vindesine

理论计算性质

JChem

• Acid pKa: 11.342998
• 质子受体: 9
• 质子供体: 5
• LogD (pH = 5.5): -2.6965613
• LogD (pH = 7.4): 0.8213256
• Log P: 2.7891831
• 摩尔折射率: 210.3222 cm^3
• 极化性: 82.5302 Å^3
• 极化表面积: 164.82 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 3.53
• LOG S: -4.03
• 溶解度: 7.00e-02 g/l

分子性质

理化性质

• 疏水性(logP): 2.9

药理学性质

• 给药途径: Intravenous
• 排泄: Biliary and renal
• 半衰期: 24 hours
• 代谢: Hepatic (CYP3A4-mediated)
• 蛋白结合率: 65-75%
• 法定药品分级: Rx-only
• 妊娠期药物分类: D (Australia)

详细说明

DrugBank - DB00309

• Drug Groups: approved
• Description: 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). [PubChem]
• Indication: For the treatment of acute leukaemia, malignant lymphoma, Hodgkin's disease, acute erythraemia and acute panmyelosis
• Pharmacology: 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 in vitro 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Half Life: 24 hours.
• Protein Binding: 65-75%
• External Links: Wikipedia; RxList