Chemical compound
Pharmaceutical compound
Cyclofenil , sold under the brand nameSexovid among others, is aselective estrogen receptor modulator (SERM) medication which is used as agonadotropin stimulant orovulation inducer and inmenopausal hormone therapy in women.[ 3] [ 4] [ 5] [ 6] [ 6] by mouth .[ 7] [ 8] [ 9]
Side effects of cyclofenil includeliver toxicity among others.[ 10] selective estrogen receptor modulator (SERM) and hence is a mixedagonist –antagonist of theestrogen receptor (ER), thebiological target ofestrogens likeestradiol .[ 8] antiestrogenic effects on thehypothalamic–pituitary–gonadal axis and hence can increasesex hormone production and stimulateovulation .[ 8] [ 11]
Cyclofenil was introduced for medical use in 1970.[ 12] Brazil ,Italy , andJapan .[ 6] [ 13] [ 3] doping agent by maleathletes .[ 8]
Cyclofenil is used to treatmenstrual disturbances andanovulatory infertility caused by insufficiency of thehypothalamic–pituitary–gonadal axis in women.[ 3] menopausal symptoms .[ 3] [ 3] [ 8] [ 9]
Cyclofenil has been available in the form of 100, 200, and 400 mgoral tablets .[ 8]
Cyclofenil has been used by maleathletes to increasetestosterone levels.[ 8] [ 8]
Cyclofenil iscontraindicated duringpregnancy and in those with severeliver disease and unexplaineduterine bleeding .[ 14]
Cyclofenil is associated with a relatively high incidence ofhepatotoxicity .[ 10] hepatitis .[ 10]
Cyclofenil is a SERM, or a mixedagonist andantagonist of theestrogen receptors (ERs).[ 8] [ 8] [ 15] progonadotropin by blocking the actions of estrogens in thepituitary gland andhypothalamus , thereby disinhibiting release of thegonadotropins luteinizing hormone andfollicle-stimulating hormone .[ 11] testosterone levels due its progonadotropic effects.[ 8]
In terms ofdistribution , cyclofenil acts bothcentrally and peripherally.[ 15] elimination half-life of cyclofenil after a single 200 mg dose is 18 to 29 hours.[ 1] [ 2]
Cyclofenil is anonsteroidal SERM and is closely related structurally totriphenylethylene SERMs likeclomifene andtamoxifen .[ 9] derivative , differing from triphenylethylenes only by the replacement of one of thephenyl rings with acyclohexane ring.[ 16] [ 11]
Cyclofenil was first introduced for medical use in 1970 under the brand name Ondogyne inFrance .[ 12] [ 12]
Society and culture [ edit ] Cyclofenil is theEnglish generic name of the drug and itsINN Tooltip International Nonproprietary Name ,USAN Tooltip United States Adopted Name , andBAN Tooltip British Approved Name .[ 4] [ 5] [ 6]
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]
Cyclofenil remains available today only inBrazil ,Italy , andJapan .[ 6] [ 13] [ 3] France ,Germany ,Mexico ,Sweden ,Switzerland ,Turkey , and theUnited Kingdom .[ 5] [ 12] [ 13] [ 3]
Cyclofenil is included on theWorld Anti-Doping Agency list of illegal doping agents in sport.[ 18] [ 19]
Cyclofenil was investigated as a possible treatment forscleroderma in the 1980s, but was found to be ineffective.[ 20] Raynaud's phenomenon in people with scleroderma also found no significant benefit.[ 21]
^a b Insler V, Lunenfeld B (January 1993).Infertility: Male and Female ISBN 978-0-443-04514-1 ^a b Blankstein J, Mashiach S, Lunenfeld B (1 July 1986).Ovulation Induction and in Vitro Fertilization ISBN 978-0-8151-0871-9 ^a b c d e f g Sweetman SC, 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 ^a b Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies ISBN 978-1-4757-2085-3 ^a b c Index Nominum 2000: International Drug Directory ISBN 978-3-88763-075-1 ^a b c d e "List of 7 Menopausal Disorders Medications Compared" .Drugs.com .^ Seyffart G (6 December 2012)."Cyclofenil" .Drug Dosage in Renal Insufficiency . Springer Science & Business Media. pp. 166–.ISBN 978-94-011-3804-8 ^a b c d e f g h i j k von Deutsch DA, Abukhalaf IK, Socci RR (15 October 2003)."Anabolic Doping Agents" . In Mozayani A, Raymon L (eds.).Handbook of Drug Interactions: A Clinical and Forensic Guide . Springer Science & Business Media. pp. 555–.ISBN 978-1-59259-654-6 ^a b c 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 ^a b c Zimmerman HJ, Ishak KG (6 December 2012)."Steroids and Other Hormones" . In Cameron R, Feuer G, de la Iglesia F (eds.).Drug-Induced Hepatotoxicity . Springer Science & Business Media. pp. 565–.ISBN 978-3-642-61013-4 ^a b c Bishop PM (22 October 2013)."Clinical Manifestations of Disorders of the Human Ovary" . In Zuckerman S, Weir BJ (eds.).Physiology . Elsevier Science. pp. 209–.ISBN 978-1-4832-5975-8 ^a b c d e William Andrew Publishing (22 October 2013).Pharmaceutical Manufacturing Encyclopedia ISBN 978-0-8155-1856-3 ^a b c d "IBM Watson Health Products" .IBM Watson Health Products . Retrieved2021-11-01 .^ Mutschler E, Derendorf H, Schäfer-Korting M, Elrod K, Estes KS (1995)."Ovaries" .Drug Actions: Basic Principles and Therapeutic Aspects . CRC Press. pp. 294–.ISBN 978-0-8493-7774-7 ^a b Tatford EP (6 December 2012)."Excessive Vaginal Bleeding" .Problems in Gynaecology . Springer Science & Business Media. pp. 105– 106.ISBN 978-94-009-4125-0 ^ Horsky J (6 December 2012)."Oestrogens" . In Horsky J, Presl J (eds.).Ovarian Function and its Disorders: Diagnosis and Therapy . Springer Science & Business Media. pp. 92–.ISBN 978-94-009-8195-9 ^ Negwer M, Scharnow HG (2001).Organic-chemical drugs and their synonyms: (an international survey) ISBN 978-3-527-30247-5 ^ Chester N (13 November 2014)."Hormone and metabolic modulators" . In Mottram DR, Chester N (eds.).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 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.doi :10.1016/S0889-857X(21)01050-4 .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 1998 (2) CD000955.doi :10.1002/14651858.CD000955 .PMC 7032887 PMID 10796397 .
Estrogens
ER Tooltip Estrogen receptor agonistsSteroidal: Alfatradiol Certainandrogens /anabolic steroids (e.g.,testosterone ,testosterone esters ,methyltestosterone ,metandienone ,nandrolone esters ) (via estrogenic metabolites) Certainprogestins (e.g.,norethisterone ,noretynodrel ,etynodiol diacetate ,tibolone ) Clomestrone Cloxestradiol acetate Conjugated estriol Conjugated estrogens Epiestriol Epimestrol Esterified estrogens Estetrol † Estradiol Estradiol esters (e.g.,estradiol acetate ,estradiol benzoate ,estradiol cypionate ,estradiol enanthate ,estradiol undecylate ,estradiol valerate ,polyestradiol phosphate ,estradiol ester mixtures (Climacteron ))Estramustine phosphate Estriol Estriol esters (e.g.,estriol succinate ,polyestriol phosphate )Estrogenic substances Estrone Estrone esters Ethinylestradiol # Hydroxyestrone diacetate Mestranol Methylestradiol Moxestrol Nilestriol Prasterone (dehydroepiandrosterone; DHEA) Promestriene Quinestradol Quinestrol Progonadotropins
Antiestrogens
ER Tooltip Estrogen receptor antagonistsSERMs Tooltip selective estrogen receptor modulators /SERDs Tooltip selective estrogen receptor downregulators )Aromatase inhibitors Antigonadotropins Androgens /anabolic steroids (e.g.,testosterone ,testosterone esters ,nandrolone esters ,oxandrolone ,fluoxymesterone )D2 receptor antagonists (prolactin releasers) (e.g.,domperidone ,metoclopramide ,risperidone ,haloperidol ,chlorpromazine ,sulpiride )GnRH agonists (e.g.,leuprorelin ,goserelin )GnRH antagonists (e.g.,cetrorelix ,elagolix )Progestogens (e.g.,chlormadinone acetate ,cyproterone acetate ,gestonorone caproate ,hydroxyprogesterone caproate ,medroxyprogesterone acetate ,megestrol acetate )Others
ER Tooltip Estrogen receptor
Agonists Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol )17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g.,testosterone andesters ,methyltestosterone ,metandienone (methandrostenolone) ,nandrolone andesters , many others; via estrogenic metabolites)Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent -EstradiolEpiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estrofurate Estrogenic substances Estromustine Estrone Etamestrol (eptamestrol) Ethinylandrostenediol Ethinylestradiol Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Xenoestrogens: Anise -related (e.g.,anethole ,anol ,dianethole ,dianol ,photoanethole )Chalconoids (e.g.,isoliquiritigenin ,phloretin ,phlorizin (phloridzin) ,wedelolactone )Coumestans (e.g.,coumestrol ,psoralidin )Flavonoids (incl.7,8-DHF ,8-prenylnaringenin ,apigenin ,baicalein ,baicalin ,biochanin A ,calycosin ,catechin ,daidzein ,daidzin ,ECG ,EGCG ,epicatechin ,equol ,formononetin ,glabrene ,glabridin ,genistein ,genistin ,glycitein ,kaempferol ,liquiritigenin ,mirificin ,myricetin ,naringenin ,penduletin ,pinocembrin ,prunetin ,puerarin ,quercetin ,tectoridin ,tectorigenin )Lavender oil Lignans (e.g.,enterodiol ,enterolactone ,nyasol (cis -hinokiresinol) )Metalloestrogens (e.g.,cadmium )Pesticides (e.g.,alternariol ,dieldrin ,endosulfan ,fenarimol ,HPTE ,methiocarb ,methoxychlor ,triclocarban ,triclosan )Phytosteroids (e.g.,digitoxin (digitalis ),diosgenin ,guggulsterone )Phytosterols (e.g.,β-sitosterol ,campesterol ,stigmasterol )Resorcylic acid lactones (e.g.,zearalanone ,α-zearalenol ,β-zearalenol ,zearalenone ,zeranol (α-zearalanol) ,taleranol (teranol, β-zearalanol) )Steroid -like (e.g.,deoxymiroestrol ,miroestrol )Stilbenoids (e.g.,resveratrol ,rhaponticin )Synthetic xenoestrogens (e.g.,alkylphenols ,bisphenols (e.g.,BPA ,BPF ,BPS ),DDT ,parabens ,PBBs ,PHBA ,phthalates ,PCBs )Others (e.g.,agnuside ,rotundifuran ) MixedSERMs Tooltip Selective estrogen receptor modulators ) Antagonists Coregulator-binding modulators: ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown
