|Trade names||Sexovid, others|
|Synonyms||Cyclophenil; F-6066; H-3452; ICI-48213; bis(p-Acetoxyphenyl)-cyclohexylidenemethane|
|AHFS/Drugs.com||International Drug Names|
|Drug class||Selective estrogen receptor modulator; Progonadotropin|
|Elimination half-life||18–29 hours|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||364.441 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. 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.
Cyclofenil is used to treat menstrual disturbances and anovulatory infertility caused by insufficiency of the hypothalamic–pituitary–gonadal axis in women. It has also been used to treat menopausal symptoms. The medication is generally used at a dosage of 400 to 600 mg per day.
Cyclofenil is associated with a relatively high incidence of hepatotoxicity. Biochemical signs of undesirable liver changes have been observed in 35% or more of individuals and 1% of individuals experience overt hepatitis.
Cyclofenil is a SERM, or a mixed agonist and antagonist of the estrogen receptors (ERs). It is described as a relatively weak/mild SERM. The medication is generally less effective than other SERMs. 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. In men, cyclofenil can increase testosterone levels due its progonadotropic effects.
Cyclofenil is a nonsteroidal SERM and is closely related structurally to triphenylethylene SERMs like clomifene and tamoxifen. 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.
Cyclofenil was first introduced for medical use in 1970 under the brand name Ondogyne in France. Subsequently, it was introduced throughout the world under a variety of other brand names, including its most well-known brand name Sexovid.
Society and culture
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.
Cyclofenil remains available today only in Brazil, Italy, and Japan. In the past, it has also been available in France, Germany, Mexico, Sweden, Switzerland, Turkey, and the United Kingdom.
Cyclofenil was investigated as a possible treatment for scleroderma in the 1980s, but was found to be ineffective. Later study of its efficacy in treating Raynaud's phenomenon in people with scleroderma also found no significant benefit.
- Vaclav Insler; Bruno Lunenfeld (January 1993). Infertility: Male and Female. Churchill Livingstone. p. 458. ISBN 978-0-443-04514-1.
- Josef Blankstein; Shlomo Mashiach; Bruno Lunenfeld (1 July 1986). Ovulation Induction and in Vitro Fertilization. Year Book Medical Publishers. p. 113. ISBN 978-0-8151-0871-9.
- Sweetman, Sean C., ed. (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 2088. ISBN 978-0-85369-840-1.
- J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 329–. ISBN 978-1-4757-2085-3.
- Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 284–. ISBN 978-3-88763-075-1.
- G. Seyffart (6 December 2012). Drug Dosage in Renal Insufficiency. Springer Science & Business Media. pp. 166–. ISBN 978-94-011-3804-8.
- Ashraf Mozayani; Lionel Raymon (15 October 2003). Handbook of Drug Interactions: A Clinical and Forensic Guide. Springer Science & Business Media. pp. 555–. ISBN 978-1-59259-654-6.
- Godwin I. Meniru; Peter R. Brinsden; Ian L. Craft (31 July 1997). A Handbook of Intrauterine Insemination. Cambridge University Press. pp. 58–59, 207. ISBN 978-0-521-58676-4.
- Ross Cameron; George Feuer; Felix de la Iglesia (6 December 2012). Drug-Induced Hepatotoxicity. Springer Science & Business Media. pp. 565–. ISBN 978-3-642-61013-4.
- Solomon Zuckerman; Barbara J. Weir (22 October 2013). Physiology. Elsevier Science. pp. 209–. ISBN 978-1-4832-5975-8.
- William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1162–. ISBN 978-0-8155-1856-3.
- Mutschler; Hartmut Derendorf (1995). Drug Actions: Basic Principles and Theraputic Aspects. CRC Press. pp. 294–. ISBN 978-0-8493-7774-7.
- E.P.W. Tatford (6 December 2012). Problems in Gynaecology. Springer Science & Business Media. pp. 105–106. ISBN 978-94-009-4125-0.
- J. Horsky; J. Presl (6 December 2012). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 92–. ISBN 978-94-009-8195-9.
- Martin Negwer; Hans-Georg Scharnow (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2397. ISBN 978-3-527-30247-5.
- David R. Mottram; Neil Chester (13 November 2014). Drugs in Sport. Routledge. pp. 117–. ISBN 978-1-134-70800-0.
- 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.
- Torres MA, Furst DE (February 1990). "Treatment of generalized systemic sclerosis". Rheum Dis Clin North Am. 16 (1): 217–41. PMID 2406809.
- Pope J, Fenlon D, Thompson A, et al. (2000). Pope J (ed.). "Cyclofenil for Raynaud's phenomenon in progressive systemic sclerosis". Cochrane Database Syst Rev (2): CD000955. doi:10.1002/14651858.CD000955. PMID 10796397.