CAS: 7599-79-3; 2-{4-[(E)-2-Chloro-1,2-Diphenylvinyl]Phenoxy}-N,N-Diethylethanami Ne 2-Hydroxy-1,2,3-Propanetricarboxylate (1:1)

该化合物是选择性雌激素受体调节器(SERM),主要用于治疗雄性低效和不孕症;它是三氯米芬静态的立体异构体,通常用于女性的排卵诱导; 内分泌功能,阻塞下丘的雌激素受体,导致蛋白质分泌增加,进而刺激睾酮产生更多的睾丸激素; 这种化合物的特点是它能够有选择地调节雌激素活动,使其有效地促进内生睾酮生产,而不会产生与外生睾酮治疗有关的不利影响; 内聚苯丙苯丙酮高原通常通过口述方式进行,具有有利于性的合成物色谱,其半衰期相对较长,允许一次服用. 其安全性特征一般都很好,但潜在的副作用可能包括热闪光,情绪波动和胃肠炎扰动. 随着研究的继续探索,生殖激素的治疗正在扩大对内分泌素的应用.

英文名称2-{4-[(E)-2-Chloro-1,2-Diphenylvinyl]Phenoxy}-N,N-Diethylethanami Ne 2-Hydroxy-1,2,3-Propanetricarboxylate (1:1)
中文名称恩氯米芬柠檬酸盐
IUPAC名称(E)-2-(4-(2-chloro-1,2-diphenylvinyl)phenoxy)-N,N-diethylethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate
CAS编号7599-79-3
MFCD编号:MFCD00058322
EINECS号:690-639-7
FDA UNII编号:J303A6U9Y6
分子式:C32H36ClNO8
分子量:598.09
产品CID: 1751798
同类组份化合物CAS7599-79-3 (citrate)15690-57-0 (free base)50-41-914158-65-7 (HCl)

相似结构搜索
InChIKey: PYTMYKVIJXPNBD-BTKVJIOYSA-N
PYTMYKVIJXPNBD-BTKVJIOYSA-N…
计算化学: 氢键受体数9.0氢键供体数4.0可旋转键数14.0

物理性质

熔点143-145°C
沸点509 °C at 760mmHg
闪点261.6 °C
PSA:144.6
LogP:5.3141
溶解性DMSO (Slightly), Ethyl Acetate (Slightly, Heated, Sonicated)
外观形态白色至类白色固体
储存条件安瓿瓶, -20°C 冷藏
产品应用该化合物是一种选择性雌激受体调节器(SERM),在低丘LAMUS中作为雌激激素对立体,增加GNRH,LH和FSH分泌.在体外,它将雌激体受体Α与IC50 ~1-2 ΜM.在体内,雄性大鼠口服10毫克/千克的血清睾酮水平显著提高(P < 0.01),对低角雄性雄性动物每日剂量为12.5-25毫克的丙烯酮,3个月中将睾酮浓度从~250 NG/DL提高到>600 NG /DL,同时保持或增加LH 和FSSH. 与外生睾酮,酶保存精子浓度和直肠轴轴功能不同,支持其作为二级假甲胺基体的生殖力分离治疗作用.

MSDS等安全信息

GHS符号GHS08
警示词Danger
危险描述H360
防范说明P264Thoroughly clean after treatmentP280Wear protective gloves/Wear protective clothing/Wear protective goggles/Wear a protective maskP305If it enters the eyesP351Rinse carefully with water for a few minutesP338Remove the contact lens(If any)And easy to operate,Continue flushingP337If eye irritation persistsP313Obtain medical advice/care
安全声明H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body

合成工艺路线路线简述

合成目标产物 Trans-Clomiphene Citrate 主要起始原料 Clomiphene Citrate
(文献来源)合成步骤主要原料 Clomiphene Citrate

海关参考信息

2901210000-乙烯
2902300000-甲苯
2902500000-苯乙烯
2903210000-氯乙烯
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专利信息

专利号:US-9914696-B2
优先权日:2014-03-11
标题:Clomiphene synthesis using a single solvent
发明人：PODOLSKI JOSEPH S; HSU KUANG
权利人:REPROS THERAPEUTICS INC
摘要:The present invention provides a one-pot method for synthesizing clomiphene (a mixture of the isomers cis-clomiphene and trans-clomiphene) utilizing a single solvent. In a preferred embodiment, the single solvent is dichloromethane (DCM, also known as methylene chloride). The present invention provides an improved method for synthesizing clomiphene and purifying clomiphene isomers.

专利号:US-6403576-B1
优先权日:1998-08-24
标题 :Antifungal and antiparasitic compounds
发明人：JACKSON JOAN E; IWU MAURICE M; OKUNJI CHRISTOPHER O; BACCHI CYRUS; TALLY JR JOHN D; AYAFOR JOHNSON F
权利人:US ARMY
摘要:Novel antiparasitic and antifungal compositions are disclosed. The antiparasitic and antifungal compositions are useful for human and veterinary therapy for the treatment and/or prevention of parasitic infection. Also disclosed are novel mechanisms of identifying antifungal and antiparasitic compositions by their biochemical action on lipid synthesis and/or metabolism and/or excretion.

其他信息查阅

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主要参考文献

1: Earl JA, Kim ED. Enclomiphene citrate: A treatment that maintains fertility in men with secondary hypogonadism. Expert Rev Endocrinol Metab. 2019 May;14(3):157-165. doi: 10.1080/17446651.2019.1612239. Epub 2019 May 7. 197(1):233. doi: 10.1016/j.juro.2016.10.018. Epub 2016 Oct 15. 119(1):171-176. doi: 10.1111/bju.13625. Epub 2016 Sep 11. 17(11):1561-7. doi: 10.1080/14656566.2016.1204294. Epub 2016 Jul 4.
5: Kovac JR. Reproductive endocrinology: Oral enclomiphene citrate in obese men with hypogonadism. Nat Rev Urol. 2016 Mar;13(3):133-4. doi: 10.1038/nrurol.2015.311. Epub 2016 Jan 20. 117(4):677-85. doi: 10.1111/bju.13337. Epub 2015 Oct 23. 193(6):2053-4. doi: 10.1016/j.juro.2015.03.052. Epub 2015 Mar 16. ZA-203 Clinical Study Group. Enclomiphene citrate stimulates testosterone production while preventing oligospermia: a randomized phase II clinical trial comparing topical testosterone. Fertil Steril. 2014 Sep;102(3):720-7. doi: 10.1016/j.fertnstert.2014.06.004. Epub 2014 Jul 17. 112(8):1188–200. doi: 10.1111/bju.12363. Epub ahead of print.
10: Kaminetsky J, Werner M, Fontenot G, Wiehle RD. Oral enclomiphene citrate stimulates the endogenous production of testosterone and sperm counts in men with low testosterone: comparison with testosterone gel. J Sex Med. 2013 Jun;10(6):1628-35. doi: 10.1111/jsm.12116. Epub 2013 Mar 26. 18(12):1947-55. doi: 10.1517/13543780903405608. 12(2):109-19. 71(4):639-44. doi: 10.1016/s0015-0282(98)00537-8. 139(9):3712-20. doi: 10.1210/endo.139.9.6177. 11(6):1250-5. doi: 10.1093/oxfordjournals.humrep.a019367. 69(10):4112-6. doi: 10.2527/1991.69104112x. 68(10):3293-9. doi: 10.2527/1990.68103293x. 45(1):104-6. doi: 10.1007/BF01990463. 65(1):217-23. doi: 10.2527/jas1987.651217x. 154(4):727-36. doi: 10.1016/0002-9378(86)90444-8.

合成参考文献

摘要:American Journal of Psychiatry., 154(1169), 1997

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