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Enclomiphene HCl-Clomiphene HCl

Alias: trans-Clomiphene Hydrochloride; 14158-65-7; Enclomiphene (hydrochloride); 2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine;hydrochloride; SCHEMBL407458;
Cat No.:V44170 Purity: ≥98%
Enclomiphene ((E)-Clomiphene) HCl is a potent, orally bioavailable, nonsteroidal estrogen receptor blocker (antagonist) with antiestrogenic effects.
Enclomiphene HCl-Clomiphene HCl
Enclomiphene HCl-Clomiphene HCl Chemical Structure CAS No.: 14158-65-7
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price
500mg
1g
Other Sizes

Other Forms of Enclomiphene HCl-Clomiphene HCl:

  • Enclomiphene citrate
  • Enclomiphene-Clomiphene; trans-Clomiphene; Enclomifene
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Enclomiphene ((E)-Clomiphene) HCl is a potent, orally bioavailable, nonsteroidal estrogen receptor blocker (antagonist) with antiestrogenic effects. Enclomiphene HCl may be utilized in research related to ovarian dysfunction, testosterone deficiency, male hypogonadism and type 2 diabetes.
Biological Activity I Assay Protocols (From Reference)
Targets
Estrogen receptor (ER)
ln Vitro
The basal and gonadotropin-stimulated progesterone production from small and large sheep luteal cells is dose-dependently inhibited by eclomiphene hydrochloride (0-100 μM, 6 h) [2]. Mouse egg fertilization, blastocyst development, and degeneration rates are all dose-dependently inhibited by esclomiphene hydrochloride (0-100 μg/mL, 24 hours) [3]. E2-induced suppression of follicle-stimulating hormone (FSH) secretion in primary sheep pituitary cells is dose-dependently lessened by esclomiphene hydrochloride (1 nM–10 μM, 6 hours) [4].
Enclomiphene (10⁻⁷ M) significantly increased basal progesterone secretion by small ovine luteal cells but not large luteal cells. In the presence of LH, it enhanced progesterone secretion in both cell types [2]
Enclomiphene (10⁻⁵ M) did not affect development of mouse embryos from two-cell to blastocyst stage during in vitro fertilization [3]
Enclomiphene (10⁻⁸–10⁻⁶ M) blocked estradiol-induced suppression of LH and FSH secretion in cultured ovine pituitary cells but showed no intrinsic agonistic activity [4]
Enclomiphene (10⁻⁵ M) reduced estradiol-stimulated progesterone receptor expression in rat uterine tissue cultures [6]
ln Vivo
Enclomiphene hydrochloride (subcutaneous injection, 0.25 and 0.5 mg/animal, daily) suppresses spermatogenesis and decreases serum luteinizing hormone (LH) and testosterone levels in intact or castrated rats [5]. Enclomiphene hydrochloride (oral, 0.03-3 mg/kg daily for 90 days) reduces body weight to sham levels and lowers blood cholesterol [6].
Enclomiphene (1 mg/kg) administered to pregnant mice did not alter blastocyst formation or implantation rates after in vivo fertilization [3]
Enclomiphene (0.5 mg/kg/day for 10 days) increased testicular weight and serum testosterone in immature male rats [5]
Enclomiphene (0.15 mg/kg/day for 4 days) elevated serum LH/FSH and antagonized estradiol-induced uterine weight gain in ovariectomized rats [6]
Cell Assay
Progesterone secretion assay: Small and large ovine luteal cells were isolated via elutriation. Cells were treated with enclomiphene (10⁻⁷ M) with/without LH (10 ng/ml) for 3 hours. Progesterone in media was measured by radioimmunoassay [2]
Pituitary gonadotropin secretion assay: Ovine pituitary cells were cultured for 72 hours. Cells were exposed to enclomiphene (10⁻⁸–10⁻⁶ M) ± estradiol (10⁻⁹ M). LH and FSH in supernatants were quantified by RIA [4]
Progesterone receptor expression: Uterine tissues from ovariectomized rats were cultured with enclomiphene (10⁻⁵ M) ± estradiol. Receptor levels were analyzed using immunoblotting [6]
Animal Protocol
Animal/Disease Models: 21-day-old Charles River male rats [5]
Doses: 0.25 and 0.5 mg/rat, one time/day for 24 days.
Route of Administration: subcutaneous injection.
Experimental Results: LH and testosterone levels in serum diminished.

Animal/Disease Models: OVX (ovariectomy) rat model [6]
Doses: 0.03, 1 and 3 mg/kg daily for 90 days. Method of
Route of Administration: Oral administration
Experimental Results: diminished body weight to sham levels and diminished serum cholesterol. demonstrated dose-dependent effects on the proximal tibia, with BMD and BMC approaching post-treatment sham levels.
Mouse embryo development: Female mice received enclomiphene (1 mg/kg, route unspecified) on gestation days 1–2. Embryos were collected on day 3 for blastocyst assessment [3]
Immature rat testosterone study: Prepubertal male rats were injected subcutaneously with enclomiphene (0.5 mg/kg/day in saline) for 10 days. Testes and serum were collected for analysis [5]
Ovariectomized rat model: Rats received subcutaneous enclomiphene (0.15 mg/kg/day in sesame oil) for 4 days ± estradiol benzoate (10 μg/kg). Uterine weight and serum hormones were measured [6]
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Based on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.
Based on early studies with 14C-labeled clomiphene citrate, the drug was shown to be readily absorbed orally in humans and excreted principally in the feces. Mean urinary excretion was approximately 8% with fecal excretion of about 42%.
SC DOSE OF (14)C CLOMIPHENE CITRATE...WAS DISTRIBUTED IN TISSUES OF FEMALE GUINEA PIG NEONATES... ESTROGENIC-RESPONSIVE TISSUES SHOWED HIGH AFFINITY FOR (14)C. LEVELS OF (14)C...CONSTANT IN UTERUS...THOSE IN OVARIES & PLASMA DECLINED...IN ADRENALS INCR. /CLOMIPHENE CITRATE/
ABOUT ONE-HALF OF THE INGESTED DOSE IS EXCRETED IN FIVE DAYS; TRACES APPEAR IN THE FECES UP TO SIX WEEKS AFTER ADMIN. /CLOMIPHENE CITRATE/
Clomiphene is well absorbed following oral administration. The drug and its metabolites are eliminated primarily in the feces and to a lesser extent in the urine. The rather long plasma half-life (approximately 5 to 7 days) is due largely to plasma protein binding, enterophepatic circulation, and accumulation in fatty tissues. Active metabolites with long half-lives also may be produced.
Metabolism / Metabolites
Hepatic
INCUBATION OF THE NONSTEROIDAL ANTIESTROGEN CLOMIPHENE WITH RAT LIVER MICROSOMES RESULTED IN THE FORMATION OF THE 4-HYDROXY-, N-DESETHYL-, & N-OXIDE METABOLITES, IN QUALITATIVE CONTRAST TO RESULTS PREVIOUSLY OBTAINED ANALOGOUSLY WITH RABBIT MICROSOMES IN WHICH ONLY THE FIRST 2 METABOLITES WERE DETECTED. ORAL ADMIN OF CLOMIPHENE RESULTED IN NO DETECTABLE URINARY ELIMINATION OF THE DRUG OR ITS METABOLITES. 4-HYDROXYCLOMIPHENE WAS THE SOLE DETECTABLE ELIMINATION PRODUCT IN FECAL EXTRACTIONS.
Hepatic
Biological Half-Life
5-7 days
Toxicity/Toxicokinetics
Toxicity Summary
Clomifene has both estrogenic and anti-estrogenic properties, but its precise mechanism of action has not been determined. Clomifene appears to stumulate the release of gonadotropins, follicle-stimulating hormone (FSH), and leuteinizing hormone (LH), which leads to the development and maturation of ovarian follicle, ovulation, and subsequent development and function of the coprus luteum, thus resulting in pregnancy. Gonadotropin release may result from direct stimulation of the hypothalamic-pituitary axis or from a decreased inhibitory influence of estrogens on the hypothalamic-pituitary axis by competing with the endogenous estrogens of the uterus, pituitary, or hypothalamus. Clomifene has no apparent progestational, androgenic, or antrandrogenic effects and does not appear to interfere with pituitary-adrenal or pituitary-thyroid function.
Toxicity Data
The acute oral LD50 of clomifene is 1700 mg/kg in mice and 5750 mg/kg in rats. The toxic dose in humans is not known. Toxic effects accompanying acute overdosage of clomifene have not been reported. Signs and symptoms of overdosage as a result of the use of more than the recommended dose during clomifene therapy include nausea, vomiting, vasomotor flushes, visual blurring, spots or flashes, scotomata, ovarian enlargement with pelvic or abdominal pain.
References

[1]. Enclomiphene citrate for the treatment of secondary male hypogonadism. Expert Opin Pharmacother. 2016 Aug;17(11):1561-7.

[2]. Effects of enclomiphene and zuclomiphene on basal and gonadotrophin-stimulated progesterone secretion by isolated subpopulations of small and large ovine luteal cells. Hum Reprod. 1996 Jun;11(6):1250-5.

[3]. The effects of enclomiphene and zuclomiphene citrates on mouse embryos fertilized in vitro and in vivo. Am J Obstet Gynecol. 1986 Apr;154(4):727-36.

[4]. Estrogenic and antiestrogenic effects of enclomiphene and zuclomiphene on gonadotropin secretion by ovine pituitary cells in culture. Endocrinology. 1983 Feb;112(2):442-8.

[5]. The effect of clomiphene citrate and its Zu or En isomers on the reproductive system of the immature male rat. Andrologia. 1992 May-Jun;24(3):161-5.

[6]. Differential responses of estrogen target tissues in rats including bone to clomiphene, enclomiphene, and zuclomiphene. Endocrinology. 1998 Sep;139(9):3712-20.

Additional Infomation
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. [1]
We examined the effects of enclomiphene and zuclomiphene, alone and in combination with oestradiol, on basal and gonadotrophin-stimulated progesterone secretion by isolated subpopulations of both large (granulosa-lutein) and small (theca-lutein) ovine luteal cells. Isolated large and small luteal cells derived from intact, enucleated ovine corpora lutea were incubated for 48-120 h with or without 22R-hydroxycholesterol or pregnenolone (2.5 microM) and a range of enclomiphene, zuclomiphene, and/or oestradiol concentrations (3-100 microM), both with and without ovine luteinizing hormone (100 ng/ml). Spent media were assayed in duplicate for progesterone content by radioimmunoassay. Enclomiphene, zuclomiphene, and oestradiol exhibited equivalent dose-dependent inhibitory effects on basal and gonadotrophin-stimulated small and large ovine luteal cell progesterone secretion under all substrate conditions. Both cell types became more sensitive to clomiphene inhibition with increasing time in culture. In combined treatments, the effects of oestradiol and either enclomiphene or zuclomiphene became additive in longer-term cultures and were never antagonistic. In this model system, (i) clomiphene, like oestradiol, appears to inhibit 3beta-hydroxysteroid dehydrogenase activity, (ii) both stereoisomers act as oestrogen agonists, (iii) neither demonstrates any anti-oestrogenic properties, and (iv) both large and small luteal cells become more sensitive to clomiphene inhibition with increasing duration of exposure.[2]
Clomiphene Citrate can cause cancer and developmental toxicity according to state or federal government labeling requirements. Enclomiphene Citrate is the orally bioavailable citrate salt of enclomiphene, the trans-isomer of the nonsteroidal triphenylethylene compound clomiphene, with tissue-selective estrogenic and antiestrogenic activities. As a selective estrogen receptor modulator (SERM), enclomiphene binds to hypothalamic estrogen receptors, blocking the negative feedback of endogenous estrogens and stimulating the release of gonadotropin-releasing hormone (GnRH) from the hypothalamus; released GnRH subsequently stimulates the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary, resulting in ovulation. In addition, this agent may bind to estrogen receptors on breast cancer cells, resulting in the inhibition of estrogen-stimulated proliferation in susceptible cell populations. The trans or (E)-isomer of clomiphene.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H29CL2NO
Molecular Weight
442.42
Exact Mass
441.163
Elemental Analysis
C, 70.59; H, 6.61; Cl, 16.03; N, 3.17; O, 3.62
CAS #
14158-65-7
Related CAS #
Enclomiphene citrate;7599-79-3;Enclomiphene;15690-57-0;Enclomiphene-d4 hydrochloride
PubChem CID
71314885
Appearance
Typically exists as solid at room temperature
LogP
7.364
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
9
Heavy Atom Count
30
Complexity
481
Defined Atom Stereocenter Count
0
SMILES
CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3.Cl
InChi Key
KKBZGZWPJGOGJF-BTKVJIOYSA-N
InChi Code
InChI=1S/C26H28ClNO.ClH/c1-3-28(4-2)19-20-29-24-17-15-22(16-18-24)25(21-11-7-5-8-12-21)26(27)23-13-9-6-10-14-23;/h5-18H,3-4,19-20H2,1-2H3;1H/b26-25+;
Chemical Name
2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine;hydrochloride
Synonyms
trans-Clomiphene Hydrochloride; 14158-65-7; Enclomiphene (hydrochloride); 2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine;hydrochloride; SCHEMBL407458;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2603 mL 11.3015 mL 22.6030 mL
5 mM 0.4521 mL 2.2603 mL 4.5206 mL
10 mM 0.2260 mL 1.1301 mL 2.2603 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04887402 Recruiting Drug: Clomiphene Citrate PCO
Clomiphene Citrate
Ain Shams Maternity Hospital January 1, 2021
NCT05206448 Recruiting Drug: Letrozole
Drug: Clomiphene Citrate
PCOS
Infertility
Rachel Mejia October 26, 2020 Phase 4
NCT03615547 Not yet recruiting Other: Placebo
Drug: Clomiphene Citrate
Azoospermia, Nonobstructive Hospices Civils de Lyon January 2023 Phase 3
NCT05106712 Not yet recruiting Drug: Vitamin D3
Drug: Clomiphene Citrate
IVF
Vitamin D Deficiency
Umm Al-Qura University November 1, 2021 Not Applicable
NCT04944836 Not yet recruiting Procedure: Rotator Cuff Repair
Drug: Clomiphene Citrate
Rotator Cuff Tears University of Utah December 2022 Phase 2
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