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Record Information
Version1.0
Creation Date2014-10-14 21:16:12 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003930
Identification
Common NameClomifene
ClassSmall Molecule
DescriptionA triphenyl ethylene stilbene derivative which is an estrogen agonist or antagonist depending on the target tissue. [PubChem]
Contaminant Sources
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Drug
  • Estrogen Antagonist
  • Fertility Agent, Female
  • Metabolite
  • Selective Estrogen Receptor Modulator
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
ClomipheneKegg
ChloramipheneMeSH
GravosanMeSH
Hydrochloride, clomipheneMeSH
ClomifeneMeSH
DynericMeSH
KlostilbegitMeSH
ClomidMeSH
Clomiphene citrateMeSH
Citrate, clomipheneMeSH
ClostilbegitMeSH
SeropheneMeSH
ClomifenMeSH
Clomiphene hydrochlorideMeSH
ClomideMeSH
Chemical FormulaC26H28ClNO
Average Molecular Mass405.970 g/mol
Monoisotopic Mass405.186 g/mol
CAS Registry Number911-45-5
IUPAC Name(2-{4-[(E)-2-chloro-1,2-diphenylethenyl]phenoxy}ethyl)diethylamine
Traditional Nameclomifene
SMILESCCN(CC)CCOC1=CC=C(C=C1)C(=C(\Cl)C1=CC=CC=C1)\C1=CC=CC=C1
InChI IdentifierInChI=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 KeyGKIRPKYJQBWNGO-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point116.5-118 °C
Boiling PointNot Available
SolubilitySlightly soluble
Predicted Properties
PropertyValueSource
Water Solubility0.00041 g/LALOGPS
logP6.08ALOGPS
logP6.47ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.76 m³·mol⁻¹ChemAxon
Polarizability46.63 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0bwa-3920000000-b910c0ca6dcc91904891View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-3791200000-10b7e9d8e7060a9b1b01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1312900000-ca9aa2374db80c007b5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udr-4933200000-164fa87cdbe23cc72977View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fi9-9451000000-5927a010de880212b24fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1323900000-270e95f39bc9c23eae50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-4129400000-86f55d0b88e5983df5a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05i0-9454000000-848ee095f1842299cd00View in MoNA
Toxicity Profile
Route of ExposureBased on early studies with 14 C-labeled clomifene, the drug was shown to be readily absorbed orally in humans.
Mechanism of ToxicityClomifene 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.
MetabolismHepatic
Toxicity ValuesThe 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.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)3, not classifiable as to its carcinogenicity to humans. (9)
Uses/SourcesUsed mainly in female infertility due to anovulation (e.g. due to polycystic ovary syndrome) to induce ovulation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06735
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEnclomifene
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID1548953
Kegg Compound IDC06917
YMDB IDNot Available
ECMDB IDNot 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.

MSDSNot Available
General ReferencesNot Available