53714-56-0

• 常用中文名：亮丙瑞林
• 常用英文名：Leuprolide TFA
• CAS号：53714-56-0
• 分子式：C₅₉H₈₄N₁₆O₁₂
• 分子量：1209.40
• 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：2018-07-29 18:48:18
• 更新时间：2026-06-30 13:27:10
• Leuprolide是一种垂体GnRH受体激动剂。

名称

• 中文名: 亮丙瑞林
• 英文名: leuprolide
• 中文别名: 醋酸亮丙瑞林 LEUPRORELINACETATE; 亮丙瑞林(LEUPRORELIN); 5-氧代-L脯氨酰-L组氨酰-L色氨酰-L丝氨酰-L酪氨酰-D亮氨酰-L亮氨酰-L精氨酰-N-乙基-L脯氨酰胺单醋酸盐; 亮丙瑞林/C1A; 亮丙瑞林,LEUPRORELIN; 利普安; 抑制剂Leuprorelin; 亮丙瑞林相关杂质; 醋酸亮丙瑞林 53-0; LEUPRELIN ACETATE 醋酸亮丙瑞林; 氘10-亮丙瑞林三氟乙酸盐; 亮丙瑞林 标准品; 醋酸亮氨酰基脯氨酸; 醋酸亮丙瑞林; LEUPRORELIN 亮丙瑞林; 亮丙瑞林-多肽制剂一致性评价; 亮丙瑞林-多肽原料委托; 亮丙瑞林醋酸盐杂质
• 英文别名: LEUPRORELIN (LEUPROLIDE) ACETATE; Leuprorelin //BP; Leuprorelinum; des-Gly10 ethylamide]gonadotropin releasing hormone; LH-RH LEUPROLIDE; Leuprorelin mesylate; GLP-HIS-TRP-SER-TYR-DLEU-LEU-G-PRO-NHET: GLP-HWSY-DL-P-NHET; pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5; LEUPRORELIN; de)-10-deglycinamide; <D-Leu6,DesGly10> LHRH ethylamide; Pyr-His-Trp-Ser-Tyr-D-Leu-Leu-g-Pro-NHEt acetate salt; PGLU-HIS-TRP-SER-TYR-P-LEU-LEU-G-PRO-NHET; DES-GLY10,[P-LEU6]-LH-RH ETHYLAMIDE; 5-OXOPRO-HIS-TRP-SER-TYR-D-LEU-LEU-G-PRO-NHC2H5; Leuprolide; nghormone; GLP-HIS-TRP-SER-TYR-DLEU-LEU-ARG-PRO-NHET: GLP-HWSY-DL-LRP-NHET; LEUPROLIDE; Anti-cancer Leuprorelin acetate; N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(diaminomethylideneamino)-1-[2-(ethylcbamoyl)-1-pyrrolidinyl]-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-(4-h; Lucrin; (DES-GLY10,D-LEU6,PRO-NHET9)-LUTEINIZING HORMONE-RELEASING HORMONE; LEUPROPELIN; Leuprorelin CRS; LUTEINIZING HORMONE-RELEASING FACTOR (SWINE), 6-D-LEUCINE-9-(N-ETHYL-L-PROLINAMIDE); GLP-HIS-TRP-SER-TYR-D-LEU-LEU-G-PRO-NHET; (d-leu(sup6),des-gly-nh2(sup10),pro-ethylamide(sup9))-gonadotropin-releasi; PGLU-HIS-TRP-SER-TYR-D-LEU-LEU-G-PRO-NHET; Leuprolide, Leuprorelin, Leuproreline, Leuprorelinum; Enantone; (DES-GLY10,D-LEU6,PRO-NHET9)-GONADOTROPIN-RELEASING HORMONE; 6-D-Leucine-9-(N-ethyl-L-prolinamide)-10-deglycinamideluteinizing hormone-releasing factor(pig); [DES-GLY10, DLEU6, PRO9]-LUTEINIZING HORMONE-RELEASING HORMONE, ETHYL AMIDE; Leuplin; Leuprorelin Acetate / Leuprorelin; [DES-GLY10, DLEU 6, PRONHET9]; PYROGLU-HIS-TRP-SER-TYR-D-LEU-LEU-G-PRO NHCH2CH3; [DES-GLY10, D-LEU6, PRO-NHET9]-LUTEINIZING HORMONE-RELEASING HORMONE HUMAN; LEUPROLIDE ACETATE PH. EUR; (DES-GLY10,D-LEU6,PRO-NHET9)-LHRH; [DES-GLY10, D-LEU6, PRO-NHET9]-LH-RH (HUMAN); (d-leu(sup6),des-gly-nh2(sup10),pro-ethylamide(sup9))-lhrh; MFCD00167544; Anti-cancer Leuprorelin acetate 74-6; Leuprorelin###Leuprorelin acetate; N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(Diaminomethylideneamino)-1-[2-(ethylcbamoyl)pyrrolidin-1-yl]-1-oxo-pentan-2-yl]cbamoyl]-3-methyl-butyl]cbamoyl]-3-methyl-butyl]cbamoyl]-2-(4-hydroxyphenyl)ethyl]cbamoyl]-2-hydroxy-ethyl]cbamoyl]-2-(1H-indol-3-yl)ethyl]cbamoyl]-2-(3H-imidazol-4-yl)ethyl]-5-oxo-pyrrolidine-2-cboxamide; LEUPROLIDE (HUMAN); 5-Oxo-L-prolil-L-histidil-L-tryptophil-L-seril-L-thyrozil-D-leucil-L-ginil-N-ethyl-L-prolinamide; [D-Leu6,des-Gly10]GnRH ethylamide; Leuprorelin Acetate(Leuprolide Acetate); Leuprelin Acetate; PYR-HIS-TRP-SER-TYR-D-LEU-LEU-G-PRO-NHET; (d-leu(sup6),des-gly-nh2(sup10),pro-ethylamide(sup9))-gnrh; Leuprorelin; luteinizinghormone-releasinghormone(pig),6-d-leucine-9-(n-ethyl-l-prolinami; 10-des-Gly-6-D-Leu-LH-RH-ethylamide; a-43818; Carcinil; Ccinil; 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide; 5-Oxo-L-Pro-L-His-L-Trp-L-Ser-L-Tyr-D-Leu-L-Leu-L-g-L-Pro-N-ethyl-NH2; [DES-GLY10, DLEU6, PRO9]-LH-RH, ETHYL AMIDE; Des-Gly10-[D-Leu6]-LH-releasing hormone ethylamide; Leuprorelin Acetate; (DES-GLY10,D-LEU6,PRO-NHET9)-LUTEINIZING HORMONE-RELEASING FACTOR; (D-Leu6, des-Gly-NH210)-LH-RH ethylamide; 1-(2-cyclohexyl-1-methylethyl)hydrazine hydrochloride

物化性质

• 密度: 1.4±0.1 g/cm3
• 分子式: C₅₉H₈₄N₁₆O₁₂
• 分子量: 1209.40
• PSA: 466.34000
• LogP: 0.41
• 外观性状: 绒毛状固体。旋光度：-31.7°
• 折射率: 1.682
• 储存条件: −20°C
• 更多:

  1.性状：蓬松固体。

  2.比旋光度：[α]_D²³-31.7°(C=1，1%乙酸)。

生物活性

• 描述: Leuprolide是一种垂体GnRH受体激动剂。
• 相关类别:
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> GNRH受体
  研究领域 >> 神经疾病
  多肽产品
• 参考文献:

  [1]. Plosker GL, Leuprorelin. A review of its pharmacology and therapeutic use in prostatic cancer, endometriosis and other sex hormone-related disorders. Drugs.1994 Dec;48(6):930-967.

  [2]. Leuprorelin

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : OK6700000 CHEMICAL NAME : Luteinizing hormone-releasing hormone (pig), 6-D-leucine-9-(N-ethyl-L-prolinamide)- 10-deglycinamide- CAS REGISTRY NUMBER : 53714-56-0 LAST UPDATED : 199201 DATA ITEMS CITED : 4 MOLECULAR FORMULA : C59-H84-N16-O12 MOLECULAR WEIGHT : 1209.59 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 5214 ug/kg SEX/DURATION : male 1 year(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct REFERENCE : FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 42,765,1984 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 280 ug/kg SEX/DURATION : female 28 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - uterus, cervix, vagina Reproductive - Maternal Effects - menstrual cycle changes or disorders REFERENCE : FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 27,853,1976 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 50 ug/kg SEX/DURATION : female 15 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) REFERENCE : PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 152,29,1976 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intravenous DOSE : 25 ug/kg SEX/DURATION : female 11 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - other measures of fertility REFERENCE : PSEBAA Proceedings of the Society for Experimental Biology and Medicine. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1903/04- Volume(issue)/page/year: 152,29,1976

安全

• 符号: GHS08
• 信号词: Danger
• 危害声明: H360
• 警示性声明: P201-P280-P308 + P313
• 安全声明 (欧洲): S22-S24/25
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: OH6390000

合成路线

914200-76-3 ~% 53714-56-0

文献：US2006/276626 A1, ; Page/Page column 13 ;

制备

苯酚和光气反应，生成氯甲酸苯酯，再和叔丁醇反应，生成叔丁氧基甲酸苯酯，接着和肼反应后，再亚硝化生成叠氮甲酸叔丁酯，然后和亮氨酸反应，得到亮氨酸侧链。
同样可以得到脯氨酸侧链。

丝氨酸和氯化苄反应以保护羟基，再和叠氮甲酸叔丁酯反应得到丝氨酸侧链。
和丝氨酸相似，可以得到酪氨酸及组氨酸的侧链。
叠氮甲酸叔丁酯和色氨酸反应后，再和2，4，6-三甲氧基苯磺酰氯反应成酯，得到色氨酸侧链。
叠氮甲酸叔丁酯和精氨酸反应，再和对甲苯磺酰氯反应，得到精氨酸侧链。
得到上述的侧链后，再进行接肽，然后和乙胺反应，再水解或氢解脱去保扩基后，精制提纯得到利普安。