Clomifene Citrate (NSC35770; NSC-35770; Omifin; Chloramiphene; Clomide; Clostilbegit; Clomid; Androxal; Dyneric; Gravosan; Klostilbegit; Serophene), the citrate salt of Clomifene, is a potent SERM (selective estrogen receptor modulator) that has been used in the treatment of ovulation induction. It acts by inhibiting the action of estrogen on the pituitary.

Physicochemical Properties

Molecular Formula	C26H28CLNO.C6H8O7
Molecular Weight	598.08
Exact Mass	597.212
CAS #	50-41-9
Related CAS #	Clomifene;911-45-5;Clomifene hydrochloride;57049-00-0
PubChem CID	3033832
Appearance	White to off-white solid powder
Boiling Point	509ºC at 760 mmHg
Melting Point	116.5-118°C
Flash Point	261.6ºC
LogP	5.314
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	14
Heavy Atom Count	42
Complexity	708
Defined Atom Stereocenter Count	0
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-OQKDUQJOSA-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-[(Z)-2-chloro-1,2-diphenylethenyl]phenoxy]-N,N-diethylethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
Synonyms	NSC-35770; Clomiphene; D; Chloramiphene; NSC35770;NSC 35770;Omifin; Citrate; Clomiphene; Clomide; Clomifen; Clostilbegit;Clomid; Androxal; Dyneric; Gravosan; Klostilbegit; Serophene
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, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In vitro activity: Clomifene competes with [3H]-QNB and [3H]-nitrendipine for their binding to the receptor in the membrane fractions from the urinary bladder and myometrium. Clomifene inhibits estrogen receptors in the hypothalamus, inhibiting negative feedback of estrogen on gonadotropinrelease, leading to up-regulation of the hypothalamic–pituitary–gonadal axis. Clomifene is a mixture of two geometric isomers, enclomifene (E-clomifene) and zuclomifene (Z-clomifene).
ln Vivo	Clomiphene citrate treatment significantly increases the chance of homosexuality and effeminized behavior in male mice.
Animal Protocol	Mice
References	Cancer Chemother Pharmacol.1990;26(4):310-2;Dongwuxue Yanjiu.2013 Oct;34(5):487-92.
Additional Infomation	Clomiphene Citrate can cause cancer and developmental toxicity according to state or federal government labeling requirements. Zuclomiphene Citrate is the cis isomer of clomiphene which exhibits weak estrogen agonist activity evaluated for antineoplastic activity against breast cancer. (NCI04) Clomiphene Citrate is the citrate salt form of clomiphene, a triphenylethylene nonsteroidal ovulatory stimulant evaluated for antineoplastic activity against breast cancer. Clomiphene has both estrogenic and anti-estrogenic activities that compete with estrogen for binding at estrogen receptor sites in target tissues. This agent causes the release of the pituitary gonadotropins follicle stimulating hormone (FSH) and luteinizing hormone (LH), leading to ovulation. (NCI04) A triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. Note that ENCLOMIPHENE and ZUCLOMIPHENE are the (E) and (Z) isomers of Clomiphene respectively. See also: Clomiphene Citrate (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO:120 mg/mL (200.6 mM) Water:<1 mg/mL Ethanol:11 mg/mL (18.4 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (4.18 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (4.18 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 25.0 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (4.18 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 7.14 mg/mL (11.94 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication (<60°C).  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.6720 mL	8.3601 mL	16.7202 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.