76932-56-4

• 常用中文名：那法瑞林
• 常用英文名：(D-2-Nal6)-LHRH acetate salt
• CAS号：76932-56-4
• 分子式：C₆₆H₈₃N₁₇O₁₃
• 分子量：1322.471
• 相关类别： 原料药 激素及调节内分泌功能类药 促性激素类药
• 发布时间：2018-04-13 08:00:00
• 更新时间：2026-07-01 10:05:12
• Nafarelin 是促性腺激素释放激素 (GnRH) 的激动剂,它能促进促黄体激素 (LH) 和促卵泡激素 (FSH) 的分泌。

名称

• 中文名: 萘法瑞林
• 英文名: Nafarelin
• 中文别名: DIVBIO/深创生物，Nafelin; NAFELIN ACETATE 醋酸那法瑞林; 萘法林; 盐酸那法瑞林; 醋酸那法瑞林 NAFELINACETATE; 6-[3-(2-萘)-D-丙氨酸]促黄体激素刺激因子; DIVBIO/深创生物,Nafelin; GNRH激活剂(NAFELIN); 那法瑞林醋酸盐; 醋酸那法瑞林; NAFELIN ACETATE,GNRH受体激动剂
• 英文别名: (2S)-N-(2-amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-(2-methylpropyl)-8-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxopyrrolidin-2-yl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}pyrrolidine-2-carboxamide (non-preferred name); RS-94991; Luteinizing hormone-releasing factor (swine), 6-[3-(2-naphthalenyl)-D-alanine]; 6-(3-(2-naphthalenyl)-d-alanine)-luteinizinghormone-releasingfactor(pig; (D-2-Nal6)-LHRH Nafelin; Synel; Nafelin; (2S)-N-(2-Amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-isobutyl-8-(2-naphthylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxopyrrolidin-2-yl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}pyrrolidine-2-carboxamide (non-preferred name); AI3; 6-(3-(2-Naphthalenyl)-D-alanine)luteinizing Hormone-releasing Factor; Nafelina [spanish]; Nafelin acetate salt; N-[1-[[1-[[1-[[1-[[1-[[1-[[1-[2-[[(2-amino-2-oxoethyl)amino]-oxomethyl]-1-pyrrolidinyl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(2-naphthalenyl)-1-oxopro; Synarel; C07613; Synrelina; Lhrh, Ala(2-naphthyl); 6-(3-(2-naphthalenyl)-d-alanine)luteinizinghormone-releasingfactor(pig); 76-0 (Monoacetate (salt)); (D-2-NAL6)-LHRH; Nacenyl; Nafelin [inn:ban]; 86-0 (Acetate (salt), hydrate); Nafelin Acetate, Nafelina; Nafelin //BP; 5-Oxo-L-Pro-L-His-L-Trp-L-Ser-L-Tyr-3-(2-naphtyl)-D-Ala-L-Leu-L-g-L-Pro-Gly-NH2; Nafelina; AI314925; UNII:1X0094V6JV; Nafarelin Acetate; Nafeline; Nasanyl; RS-94991-298; Pyr-His-Trp-Ser-Tyr-D-2-Nal-Leu-g-Pro-Gly-NH2 acetate salt; TIANFU-CHEM_Nafelin 76-4; Luteinizing hormone-releasing factor (pig), 6-(3-(2-naphthalenyl)-D-alanine); PYR-HIS-TRP-SER-TYR-D-2-NAL-LEU-G-PRO-GLY-NH2; Nafelin Acetate|(D-2-Nal6)-LHRH; ala(2-naphthyl)-lhr; Nafareline; (2S)-N-(2-Amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-isobutyl-8-(2-naphthylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxo-2-pyrrolidinyl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}-2-pyrrolidinecarboxamide; AI3-14925

物化性质

• 密度: 1.5±0.1 g/cm3
• 分子式: C₆₆H₈₃N₁₇O₁₃
• 分子量: 1322.471
• 精确质量: 1321.635620
• PSA: 472.13000
• LogP: 0.89
• 外观性状: 白色或近乎于白色冻干的粉末
• 折射率: 1.711
• 储存条件: -20°C
• 计算化学:

  1.疏水参数计算参考值（XlogP）:0.8

  2.氢键供体数量:16

  3.氢键受体数量:15

  4.可旋转化学键数量:33

  5.互变异构体数量:996

  6.拓扑分子极性表面积475

  7.重原子数量:96

  8.表面电荷:0

  9.复杂度:2730

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:9

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

生物活性

• 描述: Nafarelin 是促性腺激素释放激素 (GnRH) 的激动剂,它能促进促黄体激素 (LH) 和促卵泡激素 (FSH) 的分泌。
• 相关类别:
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> GNRH受体
  多肽产品
  研究领域 >> 癌症
• 靶点:

  GnRH[1].

• 体外研究: Nafarelin是一种促性腺激素释放激素(GnRH)激动剂,可刺激黄体生成素(LH)和卵泡刺激素(FSH)的分泌[1]。 Nafarelin有效地用于体外受精计划。 Nafarelin在鼻内给药后容易且迅速吸收,并在一定程度上受到酶促降解GnRH的保护[2]。
• 参考文献:

  [1]. Letassy NA et al. Nafarelin acetate: a gonadotropin-releasing hormone agonist for the treatment of endometriosis. DICP. 1990 Dec, 24(12):1204-9.

  [2]. Chrisp P et al. Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions.Drugs. 1990 Apr;39(4):523-51.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : OK6371150 CHEMICAL NAME : Luteinizing hormone-releasing factor (pig), 6-(3-(2-naphthalenyl)-D-alanine)- CAS REGISTRY NUMBER : 76932-56-4 LAST UPDATED : 199703 DATA ITEMS CITED : 1 MOLECULAR FORMULA : C66-H83-N17-O13 MOLECULAR WEIGHT : 1322.66 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 448 ug/kg/8W-I TOXIC EFFECTS : Nutritional and Gross Metabolic - changes in potassium REFERENCE : LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 347,333,1996

制备

N-乙酰基-2-氰基甘氨酸乙酯在乙醇中，和2-溴甲基萘反应，然后酸性水解，得到化合物(Ⅰ)。(Ⅰ)先乙酰化，再和甲醇成酯，生成化合物(Ⅱ)。(Ⅱ)经分离得到D-构型(Ⅲ)，接着用6mol/L盐酸水解，得化合物(Ⅳ)。(Ⅳ)转化为N-叔丁氧羰基衍生物(V)，在二苯甲基胺树脂上，用固相法合成得到那法瑞林。