Enclomiphene citrate

Alias: ICI-46476; ICI 46476; ICI46476; RMI-16289; RMI 16289; RMI16289; (E)-Clomiphene citrate; Androxal; Enclomiphene citrate; Enclomid

Cat No.:V19199 Purity: ≥98%

COA Product Data Instructions for use SDS

Enclomiphene citrate, formerly known as ICI-46476, RMI-16289 and trans-Clomiphene, is an orally bioavailable non-steroidal estrogen receptor antagonist in development for secondary hypogonadism in overweight men wishing to restore normal testicular function.

Enclomiphene citrate Chemical Structure CAS No.: 7599-79-3
Product category: ERR

This product is for research use only, not for human use. We do not sell to patients.

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J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

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Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

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Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Enclomiphene citrate, formerly known as ICI-46476, RMI-16289 and trans-Clomiphene, is a non-steroidal estrogen receptor antagonist that can be taken orally that is being developed as a treatment for secondary hypogonadism in overweight men who want to get their testicles back to normal. Unlike replacement, orally bioavailable enclomiphene citrate increases testosterone and maintains sperm counts in obese hypogonadal men.

Biological Activity I Assay Protocols (From Reference)

Targets

estrogen receptor

ln Vitro

Enclomiphene citrate (0-100 μM, 6 h) suppresses gonadotrophin- and basal-stimulated small- and large-scale ovine luteal cell progesterone secretion in a dose-dependent manner[2].
Enclomiphene citrate (0-100 μg/mL, 24 h) dose-dependently suppresses the rates of blastocyst formation, degeneration, and fertilization in mouse oocytes[3].
Enclomiphene citrate (1 nM-10 μM, 6 h) dose-dependently reduces E2-induced inhibition of follicle stimulating hormone (FSH) secretion in primary sheep pituitary cells[4].

ln Vivo

In intact or castrated rats, clomiphene citrate (subcutaneous injection, 0.25 and 0.5 mg/animal, daily) inhibits spermatogenesis and lowers serum levels of testosterone and luteinizing hormone (LH)[5].
Enclomiphene citrate reduces serum cholesterol and body weight to sham levels when administered orally at a dose of 0.03–3 mg/kg per day for 90 days[6].

Animal Protocol

Mice

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.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C32H36CLNO8
Molecular Weight	598.089
Exact Mass	597.2129
Elemental Analysis	C, 64.26; H, 6.07; Cl, 5.93; N, 2.34; O, 21.40
CAS #	7599-79-3
Related CAS #	Enclomiphene;15690-57-0;Clomiphene-d5 citrate;1217200-17-3;Enclomiphene hydrochloride;14158-65-7
Appearance	Solid powder
SMILES	CCN(CC)CCOC1=CC=C(C=C1)/C(=C(\C2=CC=CC=C2)/Cl)/C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChi Key	PYTMYKVIJXPNBD-BTKVJIOYSA-N
InChi Code	InChI=1S/C26H28ClNO.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-18H,3-4,19-20H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/b26-25+
Chemical Name	2-[4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
Synonyms	ICI-46476; ICI 46476; ICI46476; RMI-16289; RMI 16289; RMI16289; (E)-Clomiphene citrate; Androxal; Enclomiphene citrate; Enclomid
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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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)	DMSO: ~100 mg/mL (~167.2 mM) Ethanol: ~2 mg/mL (~3.3 mM)
Solubility (In Vivo)	Solubility in Formulation 1: ≥ 0.83 mg/mL (1.39 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.83 mg/mL (1.39 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More Solubility in Formulation 3: ≥ 0.83 mg/mL (1.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.)

Solubility (In Vitro)

DMSO: ~100 mg/mL (~167.2 mM)
Ethanol: ~2 mg/mL (~3.3 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 0.83 mg/mL (1.39 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 0.83 mg/mL (1.39 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

View More

Solubility in Formulation 3: ≥ 0.83 mg/mL (1.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 8.3 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6720 mL	8.3599 mL	16.7199 mL
	5 mM	0.3344 mL	1.6720 mL	3.3440 mL
	10 mM	0.1672 mL	0.8360 mL	1.6720 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.

Calculator

Mass

Concentration

Volume

Molecular Weight*

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

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Calculation results

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.

Note： (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

Biological Data

Chemical structure of Enclomiphene Citrate. Expert Opin Pharmacother . 2016 Aug;17(11):1561-7.