Clomifene (CED0003384)

Record Information

Version

1.0

Creation Date

2014-10-14 21:16:12 UTC

Update Date

2026-05-14 16:51:34 UTC

Accession Number

CHEM003930

Identification

Common Name

Clomifene

Class

Small Molecule

Description

Clomifene is an exogenous organic compound with the formula C26H28ClNO and an average molecular weight of 405.97 g/mol. It exists as a solid at room temperature. Clomifene belongs to the stilbenes, a class of phenylpropanoids and polyketides within the organic compounds. As a triphenyl ethylene stilbene derivative, it acts as an estrogen agonist or antagonist depending on the target tissue. The compound targets the estrogen receptor (ESR1) and estrogen receptor beta (ESR2). It is found in or released from two recorded sources: food, food processing and cookware (specifically processing fish), and healthcare, pharmaceuticals and veterinary products, where it is used as a gonadotropin and other ovulation stimulant. The recorded route of exposure for this compound is oral.

Contaminant Type

Drug
Estrogen Antagonist
Fertility Agent, Female
Metabolite
Selective Estrogen Receptor Modulator
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Clomiphene	Kegg
Chloramiphene	MeSH
Gravosan	MeSH
Hydrochloride, clomiphene	MeSH
Clomifene	MeSH
Dyneric	MeSH
Klostilbegit	MeSH
Clomid	MeSH
Clomiphene citrate	MeSH
Citrate, clomiphene	MeSH
Clostilbegit	MeSH
Serophene	MeSH
Clomifen	MeSH
Clomiphene hydrochloride	MeSH
Clomide	MeSH

Chemical Formula

C₂₆H₂₈ClNO

Average Molecular Mass

405.970 g/mol

Monoisotopic Mass

405.186 g/mol

CAS Registry Number

911-45-5

IUPAC Name

(2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}ethyl)diethylamine

Traditional Name

clomifene

SMILES

CCN(CC)CCOC1=CC=C(C=C1)C(=C(\Cl)C1=CC=CC=C1)\C1=CC=CC=C1

InChI Identifier

InChI=1S/C26H28ClNO/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/b26-25+

InChI Key

GKIRPKYJQBWNGO-OCEACIFDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Diphenylmethane
Phenoxy compound
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Ether
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	116.5-118 °C
Boiling Point	Not Available
Solubility	Slightly soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.00041 g/L	ALOGPS
logP	6.08	ALOGPS
logP	6.47	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.47 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.76 m³·mol⁻¹	ChemAxon
Polarizability	46.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bwa-3920000000-b910c0ca6dcc91904891	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-3791200000-10b7e9d8e7060a9b1b01	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1312900000-ca9aa2374db80c007b5f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udr-4933200000-164fa87cdbe23cc72977	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fi9-9451000000-5927a010de880212b24f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1323900000-270e95f39bc9c23eae50	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pb9-4129400000-86f55d0b88e5983df5a4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05i0-9454000000-848ee095f1842299cd00	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

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. 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.

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (9)

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2314.0	Log mg/kg	[1300:4100]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
323	Gonadotropins and other ovulation stimulants	Healthcare, pharmaceuticals & veterinary products	Not Available
551	Processing Fish	Food, food processing & cookware	Not Available
584	Buoys	Marine, shipping & aquaculture	Not Available
598	Fertiliser Distributors	Agriculture & land management	Not Available

Pathways

1 pathway

Clomifene Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	1.01204
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase	Q15125	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	C-8 sterol isomerase ERG2	P32352	Baker's yeast	Predicted (SEA)	0.0778492
Click to view 3D structure	Estrogen receptor	P03372	Humans	Predicted (SEA)	1.55698
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P08172	Humans	Predicted (SEA)	2.64687
Click to view 3D structure	Muscarinic acetylcholine receptor M1	P11229	Humans	Predicted (SEA)	6.92858
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	4.82665
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	3.97031
Click to view 3D structure	Epidermal growth factor receptor	P00533	Humans	Predicted (SEA)	95.4431
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	52.9375
Click to view 3D structure	Tyrosine-protein kinase Fyn	P06241	Humans	Predicted (SEA)	34.1758
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	31.6068
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	43.9848
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	44.5298
Click to view 3D structure	Muscarinic acetylcholine receptor M5	P08912	Humans	Predicted (SEA)	3.19182
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	12.7673
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	9.6533
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	26.313
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	22.732
Click to view 3D structure	Alpha-2A adrenergic receptor	P08913	Humans	Predicted (SEA)	14.7135
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	34.2537
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	9.49761
Click to view 3D structure	Substance-K receptor	P21452	Humans	Predicted (SEA)	6.22794
Click to view 3D structure	Bile salt export pump	O95342	Humans	Predicted (SEA)	2.41333
Click to view 3D structure	Estrogen receptor	P03372	Humans	Known	Not Available
Click to view 3D structure	Estrogen receptor beta	Q92731	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB06735

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Enclomifene

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

1548953

Kegg Compound ID

C06917

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Allen, R.E., Palopoli, F.P., Schumann, E.L. and Van Carnpen, M.G. Jr.; US. Patent 2,914,563; November 24, 1959; assigned to The Wrn. S. Merrell Company.

MSDS

Not Available

General References

Clomifene (CED0003384)

Structure for CHEM003930: Clomifene

Structure