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Ethinylestradiol

(British Approved Name, rINNM)

Drug Nomenclature

Synonyms: Aethinyloestradiolum; Ethinyl Estradiol; Ethinylestradiol; Ethinylestradiolum; Ethinyloestradiol; Etinilösztradiol; Etinilestradiol; Etinilestradiolis; Etinylestradiol; Etinyyliestradioli; NSC-10973
BAN: Ethinylestradiol
INN: Ethinylestradiol [rINN (en)]
INN: Etinilestradiol [rINN (es)]
INN: Éthinylestradiol [rINN (fr)]
INN: Ethinylestradiolum [rINN (la)]
INN: Етинилэстрадиол [rINN (ru)]
Chemical name: 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol; 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17β-diol
Molecular formula: C20H24O2 =296.4
CAS: 57-63-6
ATC code: G03CA01; L02AA03
Read code: y00XB [Malignancy]; y08DW [Endocrine]; y02aL

Note. Compounded preparations of ethinylestradiol may be represented by the following names:

• Co-cyprindiol (BAN) — ethinylestradiol 35 parts and cyproter-one acetate 2000 parts (w/w).

Pharmacopoeias. In China, Europe, International, Japan, and US.

European Pharmacopoeia, 6th ed. (Ethinylestradiol). A white to slightly yellowish-white, crystalline powder. Practically insoluble in water freely soluble in alcohol dissolves in dilute alkaline solutions. Protect from light.

The United States Pharmacopeia 31, 2008 (Ethinyl Estradiol). A white to creamy white, odourless, crystalline powder. Insoluble in water soluble in alcohol, in chloroform, in ether, in vegetable oils, and in solutions of fixed alkali hydroxides. Store in nonmetallic airtight containers. Protect from light.

Adverse Effects and Precautions

As for oestrogens in general (see Estradiol). See also under Hormonal Contraceptives.

Effects on calcium homoeostasis. Two patients with meta-static breast cancer given ethinylestradiol developed rapidly progressive irreversible and fatal hypercalcaemia, considered to be due to stimulation of osteolysis by the oestrogen.

Effects on the liver. Cholestasis and pruritus developed in a liver transplant recipient receiving ethinylestradiol at a dose of 50 micrograms daily for the treatment of menorrhagia. Symptoms subsided on withdrawal of ethinylestradiol but returned on its re-introduction.

Interactions

See under Hormonal Contraceptives.

Pharmacokinetics

Ethinylestradiol is rapidly and well absorbed from the gastrointestinal tract. The presence of an ethinyl group at the 17-position greatly reduces hepatic first-pass metabolism compared with estradiol, enabling the compound to be much more active by mouth, but there is some initial conjugation by the gut wall, and the systemic bioavailability is only about 40%. Ethinylestradiol is highly protein bound, but unlike naturally occurring oestrogens, which are mainly bound to sex-hormone binding globulin, it is principally bound to albumin. It is metabolised in the liver, initially by aromatic hydroxylation catalysed by the cytochrome P450 isoenzyme CYP3 A4, to form 2-hydroxyethinylestradiol and various conjugated metabolites. These are excreted in urine and faeces. Metabolites undergo enter-ohepatic recycling.

Uses and Administration

Ethinylestradiol is a synthetic oestrogen with actions similar to those of estradiol. It is frequently used as the oestrogenic component of combined oral contraceptive preparations a typical daily dose is 20 to 40 micrograms (for guidance on appropriate dose). Ethinylestradiol betadex clathrate has been used similarly in combined oral contraceptives. Ethinylestradiol is also used in a combined contraceptive transdermal patch. A dose of 20 micrograms ethinylestradiol is released daily with norelgestromin. A new patch is applied each week for 3 weeks of a 4-week cycle. Oestrogen exposure from such a patch may be higher than with a comparable oral contraceptive. A combined contraceptive vaginal ring device delivering an average of 15 micrograms ethinylestradiol daily with etonogestrel is also available it remains in the vagina for 3 weeks and is then removed for a one-week break, after which a new ring is inserted. Ethinylestradiol has also been used orally as an emergency contraceptive combined with levonorgestrel or norgestrel. A combined preparation of ethinylestradiol with the anti-androgen cyproterone is used for the hormonal treatment of acne and hirsutism, particularly when contraception is also required (see Uses and Administration, under Cyproterone Acetate).

Ethinylestradiol has also been used for menopausal HRT, although natural oestrogens are usually preferred. Oral doses of 10 to 50 micrograms daily have been given cyclically (with a progestogen in women with a uterus), but preparations providing lower doses of 2.5 or 5 micrograms daily are also available.

For the treatment of female hypogonadism, doses of 10 to 50 micrograms daily on a cyclical basis have been used.

For the palliative treatment of prostate cancer doses of 150 micrograms to 3 mg have been given daily. For palliation of malignant neoplasms of the breast in postmenopausal women doses of 100 micrograms to 1 mg three times daily have been used.

Administration in children. Although unlicensed in the UK for use in children, the BNFC does include doses of ethinylestradiol. An initial oral dose of 2 micrograms daily may be used in the management of delayed puberty in girls. This may be increased every 6 months to 5 micrograms, then to 10 micrograms, then to 20 micrograms daily, according to response. After 12 to 18 months of treatment, a progestogen should be added for 7 days of each 28-day cycle. A daily dose of ethinylestradiol 20 micrograms with cyclical progestogen may then be used to maintain sexual maturation. For the prevention of constitutional tall stature, ethinylestradiol may be given to girls aged 2 to 12 years old in a dose of 20 to 50 micrograms daily (see also Growth Disorders in Estradiol). Growth hormone provocation testing may be used in the diagnosis of growth hormone deficiency in children with growth retardation. However, the response can be blunted in prepu-bertal and peripubertal children, resulting in false negative results. Hormonal pituitary priming using ethinylestradiol has been tried in both boys and girls in order to increase responsiveness to the test, although there appears to be no consensus on such use. The BNFC includes an oral dose of 100 micrograms daily for 3 days before the test, for girls with a bone age above 10 years.

Preparations

British Pharmacopoeia 2008: Ethinylestradiol Tablets; Levonorgestrel and Ethinylestradiol Tablet

The United States Pharmacopeia 31, 2008: Desogestrel and Ethinyl Estradiol Tablets; Ethinyl Estradiol Tablets; Ethynodiol Diacetate and Ethinyl Estradiol Tablets; Levonorgestrel and Ethinyl Estradiol Tablets; Norethinclrone Acetate and Ethinyl Estradiol Tablets; Norethindrone and Ethinyl Estradiol Tablets; Norgestimate and Ethinyl Estradiol Tablets; Norgestrel and Ethinyl Estradiol Tablets

Proprietary Preparations

Argentina: Diva Total

Austria: Progynon C

Czech Republic: Minerva

Germany: Progynon C ; Turisteron

Hungary: Mikrofollin

India: Lynoral

Indonesia: Lynoral

Israel:Progynon C

Portugal: Jeanine

Russia: Microfollin

South Africa: Estinyl

Sweden: Diane

Switzerland: Elleacnelle

Thailand: Manodiol

USA: Estinyl

Multi-ingredient Preparations

The symbol ¤ denotes a preparation which is discontinued or no longer actively marketed.

Austria: Cileste; Diane; Donnina; Etalontin¤; FemHRT; Gracial; Gynovin; Harmonette; Jeanine; Laurina; Levlen¤; Liberel; Liogynon¤; Loette; Lyndiol¤; Madonella; Marvelon; Meliane; Mercilon; Microgynon; Minerva; Minesse; Minulet; Mirelle; Monogestin¤; Myvlar¤; Neo-Stediril; Neogynon; Neorlest¤; NuvaRing; Orlest¤; Ostro-Primolut¤; Ovanon¤; Ovranette; Ovysmen; Perikursal; Primosiston; Restovar¤; Sequilar; Stediril D; Sterigynon; Tri-Minulet; TriCilest; Trigynon; Trinordiol; Trinovum; Triodena; Triogestena¤; Triogestin¤; Valette; Vivelle; Yasmin; Yermonil¤; Yirala; Belgium: Binordiol¤; Cilest; Conova¤; Diane; Evra; Femodene; Fysioquens¤; Gracial; Harmonet; Lowette; Lyndiol¤; Marvelon; Meliane; Mercilon; Microgynon; Minestril¤; Ministat¤; Minulet; Mirelle; Neo-Stediril¤; Neogynon; NuvaRing; Ovanon¤; Ovidol; Ovostat¤; Ovulen¤; Ovysmen; Stediril 30; Stediril D; Stediril¤; Tri-Minulet; Trigynon; Trinordiol; Trinovum; Triodene; Yasmin; Canada: Alesse; Brevicon; Cyclen; Demulen; Diane; Evra; FemHRT; Loestrin 1.5/30; Marvelon; Min-Ovral; Minestrin; Neo-Mens¤; Norlestrin¤; Ortho 0.5/35; Ortho 1/35; Ortho 10/11¤; Ortho 7/7/7; Ortho-Cept; Ovral; Select 1/35; Synphasic; Tri-Cyclen; Triphasil; Triquilar; Denmark: Cilest; Conova¤; Desorelle; Diane; Dystrol¤; Econ¤; Evra; Feminil; Fironetta¤; Gestonette; Gracial; Gynatrol¤; Gynera; Harmonet; Lindynette; Lyndiol¤; Malonetta; Marvelon; Meloden; Mercilon; Microgyn; Milvane; Minulet; Neogentrol¤; Neogynon; Novynette; NuvaRing; Tetragynon¤; Tri-Minulet; Triminetta; Trinordiol; Trinovum; Triquilar; Yasmin; Finland: Cilest; Diane; Evra; Femoden; Gracial; Harmonet; Marvelon; Meliane; Mercilon; Microgynon; Minulet; Mirelle; Neo-Primovlar¤; NuvaRing; Tri-Femoden; Tri-Minulet; Trikvilar; Trinordiol; Yasmin; France: Adepal; Cilest; Cycleane; Daily; Diane; Effiprev; Evepar; Evra; Gynophase¤; Gynovlane¤; Harmonet; Holgyeme; Jasmine; Ludeal; Lumalia; Lutestral¤; Meliane; Melodia; Mercilon; Milli Anovlar¤; Minerva; Minesse; Minidril; Miniphase; Minulet; Moneva; Normapause¤; Norquentiel¤; NuvaRing; Ortho-Novum 1/35; Ovanon¤; Ovariostat¤; Pauseril¤; Phaeva; Physiostat¤; Planor¤; Stediril; Tetragynon¤; Trentovlane¤; Tri-Minulet; Triafemi; TriCilest; Triella; Trinordiol; Varnoline; Germany: Anacyclin 28¤; Anacyclin¤; Belara; Biviol; Certostat¤; Cilest; Conceplan M; Cyclosa; Deposiston¤; Desmin; Diane; Duoluton¤; Ediwal¤; Etalontin¤; Eugynon¤; Eve; Evra; Femigoa; Femovan; Femranette mikro; Gravistat; Lamuna; Leios; Lovelle; Lovina¤; Lyn-ratiopharm-Sequenz; Lyn-ratiopharm¤; Lyndiol¤; Marvelon; Menova¤; Microgynon; Minisiston; Minulet; Miranova; MonoStep; Neo-Eunomin; Neo-Stediril¤; Neogynon 28¤; Neogynon; Neorlest¤; Non-Ovlon¤; Nora-ratiopharm; Noracyclin¤; NovaStep; Novial; Nuriphasic¤; NuvaRing; Oestro-Gynaedron¤; Orlest¤; Ostro-Primolut¤; Ovanon¤; Oviol; Ovoresta M; Ovoresta¤; Ovowop¤; Ovysmen¤; Perikursal¤; Petibelle; Poly-Gynaedron¤; Pramino; Pregnon L¤; Primosiston¤; Progylut¤; Prosiston¤; Sequilar; Sequostat¤; Sinovula¤; Stediril 30¤; Stediril D¤; Stediril¤; Synphasec; Tetragynon¤; Triette; Trigoa; Trinordiol¤; Trinovum; Triquilar; Trisiston; TriStep; Valette; Yasmin; Yermonil¤; India: Duoluton-L; Femilon; Ginette; Mixogen; Novelon; Ovral; Triquilar; Ireland: Binovum¤; Brevinor; Cilest; Conova¤; Dianette; Eugynon 30¤; Evra; Femodene; Logynon; Marviol; Mercilon; Microgynon 30¤; Microlite; Minesse¤; Minulet; Normin¤; NuvaRing; Ovran 30¤; Ovran¤; Ovranette; Ovysmen¤; Tri-Minulet; Trinordiol; Trinovum¤; Triodene; Yasmin; Israel: Diane; Evra; Feminet; Gynera; Harmonet; Logynon¤; Meliane; Mercilon; Microdiol; Microgynon; Minesse; Minulet; Neogynon¤; Nordette; Ortho Cyclen; Trinordiol¤; Yasmin; Italy: Anovlar¤; Arianna; Binordiol¤; Bivlar¤; Cilest¤; Diane; Dueva; Egogyn; Estro-Primolut¤; Eugynon¤; Evanor-D¤; Evra; Fedra; Ginoden; Gracial; Harmonet; Loette; Lyndiol E¤; Mercilon; Microgynon; Milvane; Minesse; Miniluteolas¤; Minulet; Miranova; Novogyn; NuvaRing; Ovranet¤; Planum; Practil; Primosiston¤; Securgin; Tri-Minulet; Trigynon; Trinordiol; Trinovum¤; Yasmin; Japan: Ange; Netherlands: Alesse; Binordiol¤; Cilest; Diane; Femodeen; Fysioquens¤; Gracial; Harmonet; Lyndiol; Marvelon; Meliane; Mercilon; Microgynon; Mini Pregnon¤; Ministat; Minulet; Modicon; Neo-Stediril¤; Neocon; Neogynon; Ovanon¤; Ovidol; Ovostat; Ovulen¤; Pregnon¤; Primosiston¤; Stediril 20,30, and Stediril D; Tri-Minulet; Trigynon; Trinordiol; Trinovum; Triodeen; Norway: Diane; Eugynon¤; Evra; Follimin; Loette; Lyndiol¤; Marvelon; Microgynon; NuvaRing; Synfase; Tetragynon¤; Trinordiol; Trionetta; Yasmin; Russia: Anteovin (Антеовин); Belara (Белара); Cilest (Силест); Diane (Диане); Femoden (Фемоден); Jeanine (Жанин); Lindynette (Линдинет); Logest (Логест); Marvelon (Марвелон); Mercilon (Мерсилон); Microgynon (Микрогинон); Minisiston (Минизистон); Non-Ovlon (Нон-овлон); Novynette (Новинет); Ovidon (Овидон); Regulon (Регулон); Tri-Merci (Три-Мерси); Tri-Regol (Три-Регол); Triquilar (Триквилар); Trisiston (Тризистон); Spain: Diane; Eugynon¤; Evra; Gracial; Gynovin; Harmonet; Loette; Meliane; Melodene 15; Microdiol; Microgynon; Minesse; Minulet; Neo Lyndiol¤; Neogynona; NuvaRing; Ovoplex; Ovoresta Micro¤; Planum¤; Primosiston¤; Prolorfin¤; Suavuret; Tri-Minulet; Triagynon; Triciclor; Trigynovin; Yasmin; Yira¤; Sweden: Cilest; Desolett; Evra; Follimin; Follinett; Lyndiol¤; Lyndiolett¤; Mercilon; Neovletta; Nordette¤; NuvaRing; Orthonett Novum; Regunon¤; Restovar; Sequilarum¤; Synfase; Tetragynon¤; Trimiron; Trinordiol; Trinovum; Trionetta; Yasmin; Switzerland: Belara; Binordiol¤; Cilest; Diane; Evra; Feminac; Gracial; Gynera; Harmonet; Lovelle¤; Marvelon; Meloden; Mercilon; Microgynon; Milvane; Minerva; Minesse; Minulet; Miranova; Mirelle; Neo-Eunomine¤; Neo-Stediril¤; Neogynon; Normophasic¤; NuvaRing; Oestro-Gynaedron¤; Ologyn; Ovanon¤; Ovidol¤; Ovostat¤; Ovulen¤; Ovysmen; Primosiston; Sequilar¤; Stediril 30; Stediril D; Tetragynon; Tri-Minulet; Trinordiol; Trinovum; Triquilar; Varnoline¤; Yasmin; Yermonil¤; United Kingdom: Acnocin; Binovum; Brevinor; Cicafem; Cilest; Conova¤; Controvlar¤; Dianette; Diva; Eugynon 30¤; Eugynon 50¤; Evra; Femodene; Femodette; Gynovlar¤; Loestrin; Logynon; Marvelon; Mercilon; Microgynon 30; Minilyn¤; Minovlar¤; Minulet; Neocon 1/35¤; Norimin; Ovran 30; Ovran¤; Ovranette; Ovysmen; Schering PC4¤; Synphase; Tri-Minulet; Triadene; Trinordiol; Trinovum ED¤; Trinovum; Yasmin; United States: Alesse; Apri; Aranelle; Aviane; Brevicon; Cesia; Cryselle; Cyclessa; Demulen; Desogen; Enpresse; Estrostep Fe; Estrostep; FemHRT; GenCept 0.5/35 and 1/35¤; GenCept 10/11¤; Genora 0.5/35 and 1/35¤; Jenest¤; Junel Fe; Kariva; Kelnor; Leena; Lessina; Levlen; Levlite; Levora; Lo/Ovral; Loestrin Fe; Loestrin; Lutera; Mircette; Modicon; Necon 10/11; Necon 0.5/35, 1/35; NEE 1/35; Nelova 0.5/35E and 1/35E¤; Nelova 10/11¤; Nelulen¤; Norcept-E¤; Nordette; Norethin 1/35E¤; Norinyl 1 + 35; Norlestrin Fe¤; Norlestrin¤; NuvaRing; Ortho Cyclen; Ortho Evra; Ortho Tri-Cyclen; Ortho-Cept; Ortho-Novum 1/35; Ortho-Novum 10/11; Ortho-Novum 7/7/7; Ovcon 35; Ovcon 50; Ovral; Portia; Preven; Previfem; Reclipsen; Seasonale; Solia; Sprintec; Tri-Levlen; Tri-Norinyl; Tri-Previfem; Tri-Sprintec; TriNessa; Triphasil; Trivora; Velivet; Yasmin; Zovia.

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