Compound: cyclofenil
SMILES: O=C(Oc1ccc(C(c2ccc(OC(=O)C)cc2)=C3CCCCC3)cc1)C
InChIKey: GVOUFPWUYJWQSK-UHFFFAOYSA-N
Synonyms: cyclofenil, 2624-43-3, Sexovid, Cyclophenil, Rehibin, Neoclym, ICI 48213, Ciclofenilo, F 6066, Cyclofenilum, 4,4'-(Cyclohexylidenemethylene)diphenol diacetate ester, ICI-48213, DTXSID4022866, F-6066, NSC-86464, J468V64WZ1, F6066, Phenol, 4-((4-(acetyloxy)phenyl)cyclohexylidenemethyl)-, acetate, DTXCID002866, 4-{[4-(acetyloxy)phenyl](cyclohexylidene)methyl}phenyl acetate, ciclofenil, 4-((4-(acetyloxy)phenyl)(cyclohexylidene)methyl)phenyl acetate, 4-((4-(Acetyloxy)phenyl)cyclohexylidenemethyl)phenol Acetate, RefChem:580306, G03GB01, 220-089-1, Ondogyne, Ondonid, Cyclophenyl, Fertodur, Cyclofenyl, Cyclopenil, Sexadieno, Oginex, Sexovar, (Cyclohexylidenemethylene)-bis(4,1-phenylene) diacetate, H 3452, Bis(p-hydroxyphenyl)cyclohexyldienemethane diacetate, 4,4'-(Cyclohexylidenemethylene)bisphenol 1,1'-Diacetate, MFCD00190153, CFN, (Cyclohexylidenemethylene)bis(4,1-phenylene) diacetate, NCGC00165767-02, [4-[(4-acetyloxyphenyl)-cyclohexylidenemethyl]phenyl] acetate, Cyclofenilum [INN-Latin], Ciclofenilo [INN-Spanish], NSC 86464, CAS-2624-43-3, Cyclofenil [INN:BAN:DCF:JAN], EINECS 220-089-1, BRN 2014687, UNII-J468V64WZ1, AI3-52271, GVOUFPWUYJWQSK-UHFFFAOYSA-N, Sexovid (TN), p-Cresol, diacetate, Bis-(p-hydroxyphenyl)-cyclohexylidenemethane diacetate, Cyclofenil (Standard), Bis(p-acetoxyphenyl)cyclohexylidenemethane, CYCLOFENIL [MI], Cyclofenil (JAN/INN), CYCLOFENIL [INN], CYCLOFENIL [JAN], 4,4'-(Cyclohexylidenmethylen)diphenyl diacetat, CYCLOFENIL [MART.], CYCLOFENIL [WHO-DD], NCIOpen2_009345, SCHEMBL132246, CHEMBL141305, (cyclohexylidenemethanediyl)dibenzene-4,1-diyl diacetate, CHEBI:31446, GLXC-08148, HMS5084O16, Cyclofenil,4,4'-(Cyclohexylidenemethylene)bisphenol1,1'-diacetate, HY-W011100R, MSK10576, NSC86464, Tox21_112259, BDBM50523931, s5393, AKOS015900207, p-CRESOL, alpha-CYCLOHEXYLIDENE-alpha-(p-HYDROXYPHENYL)-, DIACETATE, Tox21_112259_1, CCG-268218, CS-W011816, DB13472, FC20687, HY-W011100, NCGC00165767-01, NCGC00165767-03, NCGC00165767-04, AC-22576, AS-69834, Cyclofenil, >=98% (HPLC), white solid, DB-046909, NS00021958, C74360, D01281, Q513583, SR-01000944933, SR-01000944933-1, (Cyclohexylidenemethylene)di(4,1-phenylene) diacetate, BRD-K68996996-001-01-7, [4-[(4-acetoxyphenyl)-cyclohexylidene-methyl]phenyl] acetate, Cyclofenil,4,4\'-(Cyclohexylidenemethylene)bisphenol1,1\'-diacetate
Theoretical properties:
molecular_formula: C23H24O4
molecular_weight: 364.4 g/mol
exact_mass: 364.16745924 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 6
heavy_atom_count: 27
topological_polar_surface_area: 52.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Cyclofenil is an organic molecular entity.
chembl: CYCLOFENIL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Cyclofenil, sold under the brand name Sexovid among others, is a selective estrogen receptor modulator (SERM) medication which is used as a gonadotropin stimulant or ovulation inducer and in menopausal hormone therapy in women. It is mostly no longer available. The medication is taken by mouth.
Side effects of cyclofenil include liver toxicity among others. It is a selective estrogen receptor modulator (SERM) and hence is a mixed agonist–antagonist of the estrogen receptor (ER), the biological target of estrogens like estradiol. It has antiestrogenic effects on the hypothalamic–pituitary–gonadal axis and hence can increase sex hormone production and stimulate ovulation.
Cyclofenil was introduced for medical use in 1970. It has been mostly discontinued, but remains available in a few countries, including Brazil, Italy, and Japan. It has been used as a doping agent by male athletes.