Cyclofenilのソースを表示

{{Short description|Chemical compound}}
{{Distinguish|Cycloguanil}}
{{Drugbox
| IUPAC_name = [4-[(4-Acetoxyphenyl)-cyclohexylidene-methyl]phenyl] acetate
| image = Cyclofenil.svg
| image_class = skin-invert-image
| width = 250px

<!--Clinical data-->
| tradename = Sexovid, others
| Drugs.com = {{drugs.com|international|cyclofenil}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration = [[Oral administration|By mouth]]
| class = [[Selective estrogen receptor modulator]]; [[Progonadotropin]]

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life = 18–29 hours<ref name="InslerLunenfeld1993" /><ref name="BlanksteinMashiach1986" />
| excretion =

<!--Identifiers-->
| CAS_number = 2624-43-3
| ATC_prefix = G03
| ATC_suffix = GB01
| PubChem = 2898
| DrugBank =
| ChEMBL = 141305
| ChemSpiderID = 2795
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J468V64WZ1
| KEGG = D01281
| synonyms = Cyclophenil; F-6066; H-3452; ICI-48213; bis(''p''-Acetoxyphenyl)-cyclohexylidenemethane

<!--Chemical data-->
| C=23 | H=24 | O=4
| SMILES = O=C(Oc3ccc(C(/c1ccc(OC(=O)C)cc1)=C2\CCCCC2)cc3)C
}}
<!-- Definition and medical uses -->
'''Cyclofenil''', sold under the brand name '''Sexovid''' among others, is a [[selective estrogen receptor modulator]] (SERM) medication which is used as a [[progonadotropin|gonadotropin stimulant]] or [[ovulation inducer]] and in [[menopausal hormone therapy]] in women.<ref name="Martindale" /><ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA329|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=329–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA284|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=284–}}</ref><ref name="Drugs.com">{{Cite web |url= https://www.drugs.com/international/cyclofenil.html |title=List of 7 Menopausal Disorders Medications Compared | work = Drugs.com }}</ref> It is mostly no longer available.<ref name="Drugs.com" /> The medication is taken [[oral administration|by mouth]].<ref name="Seyffart2012">{{cite book| vauthors = Seyffart G | chapter = Cyclofenil |title=Drug Dosage in Renal Insufficiency| chapter-url=https://books.google.com/books?id=OavnCAAAQBAJ&pg=PA166|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-3804-8|pages=166–}}</ref><ref name="MozayaniRaymon2003" /><ref name="MeniruBrinsden1997">{{cite book| vauthors = Meniru GI, Craft IL | chapter = Ovarian stimulation for assisted reproduction technologies| veditors = Meniru GI, Brinsden PR, Craft IL |title=A Handbook of Intrauterine Insemination| chapter-url = https://books.google.com/books?id=UpNScYN8B2YC&pg=PA58 |date=31 July 1997 |publisher=Cambridge University Press |isbn=978-0-521-58676-4 |pages=58–59,207 }}</ref>

<!-- Side effects and mechanism -->
[[Side effect]]s of cyclofenil include [[liver toxicity]] among others.<ref name="CameronFeuer2012" /> It is a [[selective estrogen receptor modulator]] (SERM) and hence is a mixed [[agonist]]–[[receptor antagonist|antagonist]] of the [[estrogen receptor]] (ER), the [[biological target]] of [[estrogen]]s like [[estradiol]].<ref name="MozayaniRaymon2003" /> It has [[antiestrogen]]ic effects on the [[hypothalamic–pituitary–gonadal axis]] and hence can increase [[sex hormone]] production and stimulate [[ovulation]].<ref name="MozayaniRaymon2003" /><ref name="ZuckermanWeir2013" />

<!-- History, society, and culture -->
Cyclofenil was introduced for medical use in 1970.<ref name="Publishing2013" /> It has been mostly discontinued, but remains available in a few countries, including [[Brazil]], [[Italy]], and [[Japan]].<ref name="Drugs.com" /><ref name="Micromedex" /><ref name="Martindale" /> It has been used as a [[doping agent]] by male [[athlete]]s.<ref name="MozayaniRaymon2003" />