71486-22-1

• 常用中文名：长春瑞滨
• 常用英文名：Vinorelbine
• CAS号：71486-22-1
• 分子式：C₄₅H₅₄N₄O₈
• 分子量：778.932
• 相关类别： 原料药 抗肿瘤药 天然来源类抗肿瘤药
• 发布时间：2018-05-10 08:00:00
• 更新时间：2026-07-01 16:44:36
• Vinorelbine(KW-2307 base)是抗有丝分裂剂,能抑制Hela细胞增殖,IC50为1.25 nM。

名称

• 中文名: 长春瑞宾
• 英文名: vinorelbine
• 中文别名: 长春瑞滨杂质C(2R,8S-异构体); 长春瑞滨, 来源于长春花; 去甲长春花碱; 长春瑞滨,分析标准品; 威诺瑞滨; 长春瑞; 长春瑞滨标准品; 长春瑞滨对照品; (3,3A1R,4R,5S,5,10BR)-4-乙酰氧基-3A-乙基-9-((2R,6R,8S)-4-乙基-8-(甲氧基羰基)-1,3,6,7,8,9-六氢-2,6-甲桥氮杂环癸烷并[4,3-B]吲哚-8-基)-5-羟基-8-甲氧基-6-甲基-3A,3A1,4,5,5A,6,11,12-八氢-1H-吲哚嗪并[8,1-CD]咔唑-5-甲酸甲酯; 去甲长春花碱,诺维本,民诺宾,盖诺,异长春花碱; 长春瑞滨(去甲长春花碱,诺维本,民诺宾,盖诺,异长春花碱); 长春瑞宾|||KW-2307 BASE; 去甲长春花碱、异长春花碱; VINORELBINE 长春瑞滨; 长春瑞宾,10 MM DMSO 溶液; 长春瑞滨 71-1; 诺威本; 长春瑞滨Vinorelbine; 长春碱杂质K
• 英文别名: NSC32797; Aspidospermidine-3-cboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl- , methyl ester, (2b,3b,4b,5a,12R,19a); vinorebline; 3',4'-didehydro-4'-desoxy-8'-norvincaleucoblastine; 5-Nonylthio-8-methylthio-chinolin; vinorelbine dittrate ,navelbine,nvb; vinorelbene; Aspidospermidine-3-cboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2β,3β,4β,5α,12R,19α); methyl (3,3a1r,4r,5s,5,10br)-4-acetoxy-3a-ethyl-9-((6r,8s)-4-ethyl-8-(methoxycbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1h-indolizino[8,1-cd]cbazole-5-cboxylate; Methyl (3,3a1R,4R,5S,5,10bR)-4-acetoxy-3a-ethyl-9-((2R,6R,8S)-4-ethyl-8-(methoxycbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino[8,1-cd]cbazole-5-cboxylate; C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy; Vinorelbine Impurity C (2R,8S-Isomer); KW 2307 base; 5-Noranhydrovinblastine; Vinorelbine, 10 mM in DMSO; Vinblastine Impurity K; Navelbine base; Vinorelbine from Cathanthus roseus (L.) G. Don; Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate; 3’,4’-didehydro-4’-deoxy-c’-norvincaleukoblastin; Vinorelbine (KW-2307); 8-methylsulfanyl-5-nonylsulfanyl-quinoline; VINORELBINE; (2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(Methoxycbonyl)-2,6-Methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-Methoxy-1-Methyl-aspidosperMidine-3-ca; NVBKW-2307; NSC-32797; vinorelbine D-ttrate; 5'-noranhydrovinblastine; AspidosperMidine-3-cboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8; Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methox y-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate; Vinorelbine //BP; 3’，4'-Didehydro-4ideoxy-C’-norvincaleukoblastine; Aspidospermidine-3-cboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2b,3b,4b,5a,12R,19a)- (9CI); ANX-530, KW-2307, 5'-Noranhydrovinblastine; 3',4'-Didehydro-4'-deoxy-C'-norvincaleukoblastine; Vinorelbine(Navelbine); CL069; Navelbine(R); Aspidospermidine-3-cboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2b,3b,4b,5a,12b,19a); Quinoline,8-(methylthio)-5-(nonylthio); nor-5’-anhydrovinblastine

物化性质

• 密度: 1.4±0.1 g/cm3
• 分子式: C₄₅H₅₄N₄O₈
• 分子量: 778.932
• 精确质量: 778.394165
• PSA: 133.87000
• LogP: 4.69
• 折射率: 1.676
• 储存条件: 2-8C
• 稳定性:

  二酒石酸长春瑞滨(Vinordbine Ditartrate): C45H54N4O8?2C4H6O6。黄白色无定形粉末。溶于水或乙醇。

• 分子结构:

  1、 摩尔折射率：214.24

  2、 摩尔体积（cm³/mol）：569.7

  3、 等张比容（90.2K）：1643.1

  4、 表面张力（dyne/cm）：69.1

  5、 极化率（10-24cm3）：84.93

• 更多:

  1.比旋光度：[α]_D²⁰+52.4°(C=0.3，氯仿)。

  2.UV最大吸收(乙醇)：215，268，282，293，310nm(ε 3700，11000，9500，7600，4400)。

生物活性

• 描述: Vinorelbine(KW-2307 base)是抗有丝分裂剂,能抑制Hela细胞增殖,IC50为1.25 nM。
• 相关类别:
  信号通路 >> 自噬 >> 自噬
  信号通路 >> 细胞周期/DNA损伤 >> 微管/微管蛋白
  信号通路 >> 细胞骨架 >> 微管/微管蛋白
  研究领域 >> 癌症
• 体外研究: 长春瑞滨(0.5-5nM)在浓度为1.25nM时抑制细胞增殖50％(IC50)。浓度为8 nM的长春瑞滨时,没有细胞处于后期[1]。长春瑞滨时间依赖性地诱导雄激素依赖性(AD)和非依赖性(AI)前列腺癌细胞系中的p53和p21WAFI/CIP1表达。长春瑞滨以浓度依赖性方式刺激报告基因[2]。
• 体内研究: 长春瑞滨治疗后,第一次中性粒细胞过多发生在狗的第一次(4只狗),第二次(1)或第六次(1)长春瑞滨治疗后[3]。长春瑞滨在携带肿瘤的猫中每周耐受一次,MTD为11.5 mg/m2 [4]。
• 动物实验: 根据该研究的定义，将VRL1在0.9％NaCl中稀释至1.5mg / mL的浓度，并在5分钟内进行IV。预期的治疗间隔为7天，最多4次治疗。在每周接受4次剂量后，猫有资格每2周继续接受VRL治疗，费用由所有者承担。
• 参考文献:

  [1]. Ngan VK, et al. Mechanism of mitotic block and inhibition of cell proliferation by the semisynthetic Vinca alkaloids vinorelbine and its newer derivative vinflunine. Mol Pharmacol. 2001 Jul;60(1):225-32.

  [2]. Liu XM, et al. Unique induction of p21(WAF1/CIP1)expression by vinorelbine in androgen-independent prostate cancer cells. Br J Cancer. 2003 Oct 20;89(8):1566-73.

  [3]. Poirier VJ, et al. Toxicity, dosage, and efficacy of vinorelbine (Navelbine) in dogs with spontaneous neoplasia. J Vet Intern Med. 2004 Jul-Aug;18(4):536-9.

  [4]. Pierro JA, et al. Phase I clinical trial of vinorelbine in tumor-bearing cats. J Vet Intern Med. 2013 Jul-Aug;27(4):943-8.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : RD2530000 CHEMICAL NAME : C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy- CAS REGISTRY NUMBER : 71486-22-1 LAST UPDATED : 199706 DATA ITEMS CITED : 1 MOLECULAR FORMULA : C45-H54-N4-O8 MOLECULAR WEIGHT : 779.03 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 26 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : GTKRDX Gan to Kagaku Ryoho. Cancer and Chemotherapy. (1-8-9 Yaesu, Chuo-ku, Tokyo 103, Japan) V.1- 1974- Volume(issue)/page/year: 10,1050,1983

合成路线

89384-09-8 ~79% 71486-22-1

文献：Gueritte; Pouilhes; Mangeney; et al. European Journal of Medicinal Chemistry, 1983 , vol. 18, # 5 p. 419 - 424

89368-94-5 ~77% 71486-22-1

文献：Gueritte; Pouilhes; Mangeney; et al. European Journal of Medicinal Chemistry, 1983 , vol. 18, # 5 p. 419 - 424

89368-94-5 ~76% 89384-09-8 71486-22-1

文献：European Journal of Medicinal Chemistry, , vol. 18, # 5 p. 419 - 424

38390-45-3 ~% 71486-22-1

文献：European Journal of Medicinal Chemistry, , vol. 18, # 5 p. 419 - 424

上下游产品

上游产品  1
38390-45-3
下游产品  1
162652-95-1

制备

由脱水长春碱(Anhydmvinblastine)经1步或2步反应得到长春瑞滨，收率有所提高。