33765-68-3

• 常用中文名：奥生多龙
• 常用英文名：Oxendolone
• CAS号：33765-68-3
• 分子式：C₂₀H₃₀O₂
• 分子量：302.45100
• 相关类别： 原料药 激素及调节内分泌功能类药 雄激素及同化激素类药
• 发布时间：2018-09-18 09:53:50
• 更新时间：2024-01-13 16:49:59

• 抗雄性激素药物，有抗雄性激素作用。在前列腺直接与雄性激素发生竞争性拮抗，抑制前列腺及精囊的重量。其抗雄激素作用特异性高，在前列腺直接与雄激素发生竞争性拮抗而几乎不显示其他激素作用。适用于治疗前列腺肥大。用于前列腺肥大的治疗。
  

名称

• 中文名: 奥生多龙
• 英文名: (8R,9S,10R,13S,14S,16S,17S)-16-ethyl-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• 英文别名: Oxendolona [INN-Spanish]; Oxendolone [USAN:INN:JAN]; Tsaa 291; oxendolone; Oxendolonum [INN-Latin]; Oxendolona; Prostetin

物化性质

• 密度: 1.1g/cm3
• 沸点: 451.7ºC at 760mmHg
• 熔点: 152-153℃
• 分子式: C₂₀H₃₀O₂
• 分子量: 302.45100
• 闪点: 192.4ºC
• 精确质量: 302.22500
• PSA: 37.30000
• LogP: 4.12520
• 折射率: 1.553
• 分子结构:

  1、 摩尔折射率：87.69

  2、 摩尔体积（cm³/mol）：274.0

  3、 等张比容（90.2K）：703.3

  4、 表面张力（dyne/cm）：43.4

  5、 极化率（10-24cm3）：34.76

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:1

  3.氢键受体数量:2

  4.可旋转化学键数量:1

  5.互变异构体数量:8

  6.拓扑分子极性表面积37.3

  7.重原子数量:22

  8.表面电荷:0

  9.复杂度:508

  10.同位素原子数量:0

  11.确定原子立构中心数量:7

  12.不确定原子立构中心数量:0

  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

• 更多:

  1.性状：白色结晶性粉末

  2.熔点（ºC）：152～153

毒性和生态

毒理学数据: 急性毒性LD50大鼠和小鼠(g/kg)：＞10口服；5～10肌肉注射和腹腔注射。 CHEMICAL IDENTIFICATION RTECS NUMBER : KG7963000 CHEMICAL NAME : Estr-4-en-3-one, 16-beta-ethyl-17-beta-hydroxy- CAS REGISTRY NUMBER : 33765-68-3 LAST UPDATED : 199706 DATA ITEMS CITED : 12 MOLECULAR FORMULA : C20-H30-O2 MOLECULAR WEIGHT : 302.50 WISWESSER LINE NOTATION : L E5 B666 OV MUTJ E1 FQ G2 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 12105 mg/kg TOXIC EFFECTS : Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Lungs, Thorax, or Respiration - respiratory depression REFERENCE : YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 7,937,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 5879 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - lacrimation Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - body temperature decrease REFERENCE : YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 7,937,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 23,2291,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,157,1982 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 5480 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 12,1204,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 2925 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - lacrimation Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression REFERENCE : YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 7,937,1979 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. (Yakugyo Jihosha, Inaoka Bldg., 2-36 Jinbo-cho, Kanda, Chiyoda-ku, Tokyo 101, Japan) V.1- 1959- Volume(issue)/page/year: 23,2291,1981 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >10 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,157,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 5200 mg/kg/1Y-I TOXIC EFFECTS : Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 7,968,1979 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 150 mg/kg SEX/DURATION : male 30 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands Reproductive - Paternal Effects - other effects on male REFERENCE : YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 7,943,1979 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 15 mg/kg SEX/DURATION : female 30 day(s) pre-mating TOXIC EFFECTS : Reproductive - Maternal Effects - uterus, cervix, vagina REFERENCE : YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 7,943,1979 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intramuscular DOSE : 750 mg/kg SEX/DURATION : male 30 day(s) pre-mating TOXIC EFFECTS : Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - impotence REFERENCE : INJFA3 International Journal of Fertility. (Allen Press, 1041 New Hampshire, St., Lawrence, KS 66044) V.1- 1955- Volume(issue)/page/year: 34,235,1989

上下游产品

上游产品  3
33765-85-4 75-65-0 33765-70-7
下游产品  0

制备

将雌酚酮、二氯甲烷、氢氧化钠、三乙基苄铵盐和水，室温搅拌下，滴加硫酸二甲酯，进行甲基化反应。该甲基化产物、对甲苯磺酸和异丙烯基乙酸酯，搅拌回流，得烯醇化产物。该产物、氧化镁和二氯甲烷构成的溶液中，滴加单过氧邻苯二甲酸的乙醚溶液，进行环氧化反应。在室温和搅拌下，往环氧化产物的冰乙酸溶液中，滴加冰乙醇和硫酸的混合液，反应使环氧开环。开环产物和氢氧化钾的甲醇溶液，搅拌回流。再在四氢呋喃中，加乙基溴化镁格氏试剂，进行格氏反应。该反应产物、对甲苯磺酸和冰乙酸，搅拌回流，然后用硼氢化钠在甲醇中进行还原。最后在四氢呋喃溶液中，通入液氨，在搅拌下再缓慢加入锂，还原得奥生多龙。或者将16β-乙基雄甾-4-烯-3,17-二酮溶于二氧六环，加入原甲酸乙酯和对甲苯磺酸，在室温下搅拌，得到3-乙氧基-16β-乙基雄甾-3,5-二烯-17-酮。将其溶于甲醇，加入硼氢化钠，在室温下搅拌，还原得3-乙氧基-16-β-乙基雄甾-3,5-二烯-17β-醇。最后溶于甲醇，加入浓盐酸，水解即得奥生多龙。