Chemistry:Cyclofenil

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Short description: Chemical compound
Cyclofenil
Cyclofenil.svg
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC23H24O4
Molar mass364.441 g·mol−1
3D model (JSmol)

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]

Medical use

Cyclofenil is used to treat menstrual disturbances and anovulatory infertility caused by insufficiency of the hypothalamic–pituitary–gonadal axis in women.[3] It has also been used to treat menopausal symptoms.[3] The medication is generally used at a dosage of 400 to 600 mg per day.[3][8][9]

Available forms

Cyclofenil has been available in the form of 100, 200, and 400 mg oral tablets.[8]

Non-medical use

Cyclofenil has been used by male athletes to increase testosterone levels.[8] It is not effective for this purpose in women.[8]

Contraindications

Cyclofenil is contraindicated during pregnancy and in those with severe liver disease and unexplained uterine bleeding.[14]

Side effects

Cyclofenil is associated with a relatively high incidence of hepatotoxicity.[10] Biochemical signs of undesirable liver changes have been observed in 35% or more of individuals and 1% of individuals experience overt hepatitis.[10]

Pharmacology

Pharmacodynamics

Cyclofenil is a SERM, or a mixed agonist and antagonist of the estrogen receptors (ERs).[8] It is described as a relatively weak/mild SERM.[8] The medication is generally less effective than other SERMs.[15] The medication is an "impeded estrogen" and is thought to work as a progonadotropin by blocking the actions of estrogens in the pituitary gland and hypothalamus, thereby disinhibiting release of the gonadotropins luteinizing hormone and follicle-stimulating hormone.[11] In men, cyclofenil can increase testosterone levels due its progonadotropic effects.[8]

Pharmacokinetics

In terms of distribution, cyclofenil acts both centrally and peripherally.[15] The elimination half-life of cyclofenil after a single 200 mg dose is 18 to 29 hours.[1][2]

Chemistry

Cyclofenil is a nonsteroidal SERM and is closely related structurally to triphenylethylene SERMs like clomifene and tamoxifen.[9] It has been referred to as a diphenylethylene derivative, differing from triphenylethylenes only by the replacement of one of the phenyl rings with a cyclohexane ring.[16][11]

History

Cyclofenil was first introduced for medical use in 1970 under the brand name Ondogyne in France .[12] Subsequently, it was introduced throughout the world under a variety of other brand names, including its most well-known brand name Sexovid.[12]

Society and culture

Generic names

Cyclofenil is the English generic name of the drug and its INN, USAN, and BAN.[4][5][6]

Brand names

Cyclofenil has been marketed under a variety of brand names including Ciclifen, Fertodur, Gyneuro, Klofenil, Menoferil, Menopax, Neoclym, Oginex, Ondonid, Ondogyne, Rehibin, Sexadieno, Sexovar, and Sexovid.[17][12][13]

Availability

Cyclofenil remains available today only in Brazil , Italy, and Japan .[6][13][3] In the past, it has also been available in France , Germany , Mexico, Sweden, Switzerland , Turkey, and the United Kingdom .[5][12][13][3]

Regulation

Cyclofenil is included on the World Anti-Doping Agency list of illegal doping agents in sport.[18][19]

Research

Cyclofenil was investigated as a possible treatment for scleroderma in the 1980s, but was found to be ineffective.[20] Later study of its efficacy in treating Raynaud's phenomenon in people with scleroderma also found no significant benefit.[21]

References

  1. ↑ 1.0 1.1 Infertility: Male and Female. Churchill Livingstone. January 1993. p. 458. ISBN 978-0-443-04514-1. https://books.google.com/books?id=KCNsAAAAMAAJ. 
  2. ↑ 2.0 2.1 Ovulation Induction and in Vitro Fertilization. Year Book Medical Publishers. 1 July 1986. p. 113. ISBN 978-0-8151-0871-9. https://books.google.com/books?id=aYVsAAAAMAAJ. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. 2009. p. 2088. ISBN 978-0-85369-840-1. 
  4. ↑ 4.0 4.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 329–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA329. 
  5. ↑ 5.0 5.1 5.2 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 284–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA284. 
  6. ↑ 6.0 6.1 6.2 6.3 6.4 "List of 7 Menopausal Disorders Medications Compared". Drugs.com. https://www.drugs.com/international/cyclofenil.html. 
  7. ↑ "Cyclofenil". Drug Dosage in Renal Insufficiency. Springer Science & Business Media. 6 December 2012. pp. 166–. ISBN 978-94-011-3804-8. https://books.google.com/books?id=OavnCAAAQBAJ&pg=PA166. 
  8. ↑ 8.00 8.01 8.02 8.03 8.04 8.05 8.06 8.07 8.08 8.09 8.10 "Anabolic Doping Agents". Handbook of Drug Interactions: A Clinical and Forensic Guide. Springer Science & Business Media. 15 October 2003. pp. 555–. ISBN 978-1-59259-654-6. https://books.google.com/books?id=dwMyBwAAQBAJ&pg=PA555. 
  9. ↑ 9.0 9.1 9.2 "Ovarian stimulation for assisted reproduction technologies". A Handbook of Intrauterine Insemination. Cambridge University Press. 31 July 1997. pp. 58–59,207. ISBN 978-0-521-58676-4. https://books.google.com/books?id=UpNScYN8B2YC&pg=PA58. 
  10. ↑ 10.0 10.1 10.2 "Steroids and Other Hormones". Drug-Induced Hepatotoxicity. Springer Science & Business Media. 6 December 2012. pp. 565–. ISBN 978-3-642-61013-4. https://books.google.com/books?id=xZf-CAAAQBAJ&pg=PA565. 
  11. ↑ 11.0 11.1 11.2 "Clinical Manifestations of Disorders of the Human Ovary". Physiology. Elsevier Science. 22 October 2013. pp. 209–. ISBN 978-1-4832-5975-8. https://books.google.com/books?id=4R_FAgAAQBAJ&pg=PA209. 
  12. ↑ 12.0 12.1 12.2 12.3 12.4 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1162–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA1162. 
  13. ↑ 13.0 13.1 13.2 13.3 "IBM Watson Health Products". http://www.micromedexsolutions.com/. 
  14. ↑ "Ovaries". Drug Actions: Basic Principles and Therapeutic Aspects. CRC Press. 1995. pp. 294–. ISBN 978-0-8493-7774-7. https://books.google.com/books?id=IvN4mZxraMkC&pg=PA294. 
  15. ↑ 15.0 15.1 "Excessive Vaginal Bleeding". Problems in Gynaecology. Springer Science & Business Media. 6 December 2012. pp. 105–106. ISBN 978-94-009-4125-0. https://books.google.com/books?id=q0inBgAAQBAJ&pg=PA105. 
  16. ↑ "Oestrogens". Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. 6 December 2012. pp. 92–. ISBN 978-94-009-8195-9. https://books.google.com/books?id=7IrpCAAAQBAJ&pg=PA92. 
  17. ↑ Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. 2001. p. 2397. ISBN 978-3-527-30247-5. https://books.google.com/books?id=zmpqAAAAMAAJ. 
  18. ↑ "Hormone and metabolic modulators". Drugs in Sport. Routledge. 13 November 2014. pp. 117–. ISBN 978-1-134-70800-0. https://books.google.com/books?id=ESFWBQAAQBAJ&pg=PA117. 
  19. ↑ Ed The Emtree Editorial Team (1 January 2004). Doping Search Guide 2004: Over 10,000 Substance Names in Reference to the 2004 WADA (World Anti-Doping Agency) List of Prohibited Substances and Methods. Elsevier. p. 82. ISBN 978-0-444-51752-4. https://books.google.com/books?id=Y9ULAQAAMAAJ. 
  20. ↑ "Treatment of generalized systemic sclerosis". Rheum Dis Clin North Am 16 (1): 217–41. February 1990. doi:10.1016/S0889-857X(21)01050-4. PMID 2406809. 
  21. ↑ "Cyclofenil for Raynaud's phenomenon in progressive systemic sclerosis". Cochrane Database Syst Rev 1998 (2): CD000955. 2000. doi:10.1002/14651858.CD000955. PMID 10796397. 



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