Enclomiphene citrate
(Synonyms: 恩氯米芬柠檬酸盐; (E)-Clomiphene citrate; trans-Clomiphene citrate; Enclomifene citrate) 目录号 : GC35985
An ER modulator
Cas No.:7599-79-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Enclomiphene is an estrogen receptor (ER) modulator.1,2,3 It acts as an ER antagonist in humans, sheep, and rabbits and an ER agonist in rats.1,2,3 Enclomiphene (0.34 ?M) inhibits binding of 17β-estradiol in isolated rabbit uterus.2 It decreases E2-induced inhibition of follicle stimulating hormone (FSH) secretion in primary sheep pituitary cells in a concentration-dependent manner.3 Enclomiphene (0.25 and 0.5 mg/animal) inhibits spermatogenesis and decreases serum luteinizing hormone (LH) and testosterone levels in intact or castrated rats.4 Formulations containing enclomiphene have been used in the treatment of ovarian dysfunction.
1.Hill, S., Arutchelvam, V., and Quinton, R.Enclomiphene, an estrogen receptor antagonist for the treatment of testosterone deficiency in menIDrugs12(2)109-119(2009) 2.Wyss, R.H., Karsznia, R., Heinrichs, W.L., et al.Inhibition of uterine receptor binding of estradiol by anti-estrogens (clomiphene and CL-868)J. Clin. Endocrinol. Metab.28(12)1824-1828(1968) 3.Huang, S.-R., and Miller, W.L.Estrogenic and antiestrogenic effects of enclomiphene and zuclomiphene on gonadotropin secretion by ovine pituitary cells in cultureEndocrinology112(2)442-448(1983) 4.Weissenberg, R., Dar, Y., and Lunenfeld, B.The effect of clomiphene citrate and its Zu or En isomers on the reproductive system of the immature male ratAndrologia24(3)161-165(1992)
| Cas No. | 7599-79-3 | SDF | |
| 别名 | 恩氯米芬柠檬酸盐; (E)-Clomiphene citrate; trans-Clomiphene citrate; Enclomifene citrate | ||
| Canonical SMILES | Cl/C(C1=CC=CC=C1)=C(C2=CC=C(OCCN(CC)CC)C=C2)\C3=CC=CC=C3.O=C(CC(C(O)=O)(O)CC(O)=O)O.[(E)] | ||
| 分子式 | C32H36ClNO8 | 分子量 | 598.08 |
| 溶解度 | DMSO: ≥ 50 mg/mL (83.60 mM) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 1.672 mL | 8.3601 mL | 16.7202 mL |
| 5 mM | 0.3344 mL | 1.672 mL | 3.344 mL |
| 10 mM | 0.1672 mL | 0.836 mL | 1.672 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Enclomiphene citrate for the treatment of secondary male hypogonadism
Expert Opin Pharmacother 2016 Aug;17(11):1561-7.PMID:27337642DOI:10.1080/14656566.2016.1204294.
Introduction: Hypogonadism is a growing concern in an aging male population. Historically treated using exogenous testosterone, concerns about possible adverse effects of testosterone have led physicians to seek alternative treatment approaches. Areas covered: Enclomiphene citrate is the trans isomer of clomiphene citrate, a non-steroidal estrogen receptor antagonist that is FDA-approved for the treatment of ovarian dysfunction in women. Clomiphene citrate has also been used off-label for many years to treat secondary male hypogonadism, particularly in the setting of male infertility. Here we review the literature examining the efficacy and safety of Enclomiphene citrate in the setting of androgen deficiency. Expert opinion: Initial results support the conclusion that Enclomiphene citrate increases serum testosterone levels by raising luteinizing hormone (LH) and follicle stimulating hormone (FSH) levels, without negatively impacting semen parameters. The ability to treat testosterone deficiency in men while maintaining fertility supports a role for Enclomiphene citrate in the treatment of men in whom testosterone therapy is not a suitable option.
Enclomiphene citrate: A treatment that maintains fertility in men with secondary hypogonadism
Expert Rev Endocrinol Metab 2019 May;14(3):157-165.PMID:31063005DOI:10.1080/17446651.2019.1612239.
Hypogonadism is an important issue among the male population. Treatments such as exogenous testosterone have become very popular. One of the adverse effects of testosterone is its suppression of fertility. This has lead to the use of alternative therapies such as selective estrogen receptor modulators (SERMs) that aim to correct hypogonadism without reducing fertility. Areas covered: The SERM, clomiphene citrate, which is approved by the FDA for the treatment of ovarian dysfunction, has been shown to have beneficial effects on male hypogonadism. Clomiphene citrate exists as a mixture of both the cis-isomer (zuclomiphene) and the trans-isomer (enclomiphene). The literature has suggested that most of the beneficial effects of clomiphene are due to the trans-isomer enclomiphene. Zuclomiphene contributes little to the intended outcomes. The purpose of this drug profile is to examine the available literature on the trans-isomer enclomiphene. Expert opinion: Enclomiphene has been shown to increase testosterone levels while stimulating FSH and LH production. Initial studies demonstrated that enclomiphene maintains the androgenic benefit of clomiphene citrate without the undesirable effects attributable to zuclomiphene. This article reviews the difficulties associated with the FDA approval of a new molecular entity related to the treatment of hypogonadism.
Oral Enclomiphene citrate raises testosterone and preserves sperm counts in obese hypogonadal men, unlike topical testosterone: restoration instead of replacement
BJU Int 2016 Apr;117(4):677-85.PMID:26496621DOI:10.1111/bju.13337.
Objectives: To determine the effects of daily oral doses of Enclomiphene citrate compared with topical testosterone gel treatment on serum total testosterone (TT), luteinising hormone (LH), follicle-stimulating hormone (FSH), and sperm counts in men with secondary hypogonadism. Patients and methods: Two parallel randomised, double-blind, double-dummy, placebo-controlled, multicentre, phase III studies were undertaken to evaluate two doses of Enclomiphene citrate vs testosterone gel (AndroGel(®) 1.62%) on TT, LH, FSH, and sperm counts in overweight men aged 18-60 years with secondary hypogonadism. Men were screened and enrolled in the trials (ZA-304 and ZA-305). All enrolled men had early morning serum TT levels in the low or low normal range (≤300 ng/dL; ≤10.4 nmol/L) and had low or normal LH (<9.4 IU/L) levels measured on two separate occasions 2-10 days apart. Serum samples were obtained over the course of the study to determine relevant hormone levels at baseline and after 16 weeks of treatment. Men provided semen samples twice to enroll at the beginning and twice at the end of the study. Results: TT levels increased between baseline and after 16 weeks of treatment in all the treatment groups. FSH and LH levels increased in the Enclomiphene citrate groups and decreased in the testosterone gel group at 16 weeks. Enclomiphene citrate maintained sperm concentration in the normal range over the treatment period, while there was a marked reduction in spermatogenesis in the testosterone gel group. Conclusions: Enclomiphene citrate consistently increased serum TT, LH and FSH, restoring normal levels of serum TT. Enclomiphene citrate treatment maintained sperm concentrations in the normal range. The effects on TT were also seen with testosterone replacement via testosterone gel but sperm counts were not maintained.
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.PMID:23530575DOI:10.1111/jsm.12116.
Introduction: Clomiphene citrate is employed off-label in men who have low testosterone and for the restoration of sperm counts in men who have used exogenous testosterone. Clomiphene is a mixture of two diastereoisomers: zuclomiphene and enclomiphene. We evaluated Enclomiphene citrate in men with secondary hypogonadism. Aim: Our aim was to compare oral Enclomiphene citrate as an alternative to topical testosterone. Main outcome measures: Blood levels of total testosterone (TT), estradiol, follicle-stimulating hormone (FSH), luteinizing hormone (LH), sex hormone binding globulin, thyroid stimulation hormone, prolactin, and insulin-like growth factor 1 IGF-1 were measured at certain times after treatment with each agent. Sperm parameters were determined at the same visits. Free testosterone (FT) was calculated. Methods: This was a proof-of-principle, randomized, open-label, fixed dose, active-control, two-center phase IIB study in 12 men with secondary hypogonadism treated previously with topical testosterone. Results: After discontinuation of topical testosterone, morning TT values averaged 165 ± 66 pg/dL. After 3 months, there was a significant rise in men receiving Enclomiphene citrate and gel that was sustained for 3 months. At 6 months, TT levels were 545 ± 268 and 525 ± 256 pg/dL for groups receiving the gel and Enclomiphene citrate, respectively. Only men in the Enclomiphene citrate group demonstrated increased LH and FSH. TT decreased one month posttreatment to pretreatment values. Enclomiphene citrate elevated sperm counts in seven out of seven men at 3 months and six out of six men at 6 months with sperm concentrations in the 75-334 × 10(6) /mL range. The gel was ineffective in raising sperm counts above 20 × 10(6) /mL for all five men at 3 months and raised counts in only two or five men at 6 months. At follow-up, only Enclomiphene citrate treatment was associated with elevated sperm counts. Conclusions: Enclomiphene citrate increased testosterone and sperm counts. Concomitant changes in LH and FSH suggest normalization of endogenous testosterone production and restoration of sperm counts through the hypothalamic-pituitary-testicular axis.
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.PMID:25044085DOI:10.1016/j.fertnstert.2014.06.004.
Objective: To determine the effect of Enclomiphene citrate in men with secondary hypogonadism. Design: Phase II clinical trial. Setting: Community dwelling men making visits to physician offices. Patient(s): Men with secondary hypogonadism. Intervention(s): Oral administration of Enclomiphene citrate or 1% topical T gel. Main outcome measure(s): Luteinizing hormone, FSH, T, and semen analysis. Result(s): Treatment with Enclomiphene citrate resulted in increased morning serum T, E2, and LH levels similar to those obtained with a topical T gel in men with secondary hypogonadism. Follicle-stimulating hormone and LH were increased with enclomiphene, and sperm counts were conserved. Conclusion(s): Enclomiphene citrate reverses the two hallmarks of secondary hypogonadism, namely, low serum total T and low or inappropriately normal LH while preserving sperm production. Clinical trial registration number: NCT01270841 (ClinicalTrials.gov Identifier NCT01270841).