Cyclofenil

Not to be confused with Cycloguanil.
Cyclofenil
Clinical data
Trade namesSexovid, others
Other namesCyclophenil; F-6066; H-3452; ICI-48213; bis(p-Acetoxyphenyl)-cyclohexylidenemethane
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator; Progonadotropin
ATC code
Pharmacokinetic data
Elimination half-life18–29 hours[1][2]
Identifiers
IUPAC name
  • [4-[(4-Acetoxyphenyl)-cyclohexylidene-methyl]phenyl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.018.264
Chemical and physical data
FormulaC23H24O4
Molar mass364.441 g·mol−1
3D model (JSmol)
SMILES
  • O=C(Oc3ccc(C(/c1ccc(OC(=O)C)cc1)=C2\CCCCC2)cc3)C

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.[3][4][5][6] It is mostly no longer available.[6] The medication is taken by mouth.[7][8][9]

Side effects of cyclofenil include liver toxicity among others.[10] 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.[8] It has antiestrogenic effects on the hypothalamic–pituitary–gonadal axis and hence can increase sex hormone production and stimulate ovulation.[8][11]

Cyclofenil was introduced for medical use in 1970.[12] It has been mostly discontinued, but remains available in a few countries, including Brazil, Italy, and Japan.[6][13][3] It has been used as a doping agent by male athletes.[8]

  1. ^ Cite error: The named reference InslerLunenfeld1993 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference BlanksteinMashiach1986 was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference Martindale was invoked but never defined (see the help page).
  4. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 329–. ISBN 978-1-4757-2085-3.
  5. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 284–. ISBN 978-3-88763-075-1.
  6. ^ a b c "List of 7 Menopausal Disorders Medications Compared". Drugs.com.
  7. ^ Seyffart G (6 December 2012). "Cyclofenil". Drug Dosage in Renal Insufficiency. Springer Science & Business Media. pp. 166–. ISBN 978-94-011-3804-8.
  8. ^ a b c d Cite error: The named reference MozayaniRaymon2003 was invoked but never defined (see the help page).
  9. ^ Meniru GI, Craft IL (31 July 1997). "Ovarian stimulation for assisted reproduction technologies". In Meniru GI, Brinsden PR, Craft IL (eds.). A Handbook of Intrauterine Insemination. Cambridge University Press. pp. 58–59, 207. ISBN 978-0-521-58676-4.
  10. ^ Cite error: The named reference CameronFeuer2012 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference ZuckermanWeir2013 was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Micromedex was invoked but never defined (see the help page).
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