Peringatan Keamanan

Female patients experiencing and overdose may present with withdrawal bleeding, nausea, vomiting, breast tenderness, abdominal pain, drowsiness, and fatigue.L11944,L11965,L11947,L11950,L11845,L9806,L11953,L10304,L11956,L11959,L11962 Overdose should be treated with symptomatic and supportive care including monitoring for potassium concentrations, sodium concentrations, and signs of metabolic acidosis.L11944,L11965,L11947,L11950,L11845,L9806,L11953,L10304,L11956,L11959,L11962

Ethinylestradiol

DB00977

small molecule approved

Deskripsi

Ethinylestradiol was first synthesized in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at Schering.A191107 It was developed in an effort to create an estrogen with greater oral bioavailability.A191107 These properties were achieved by the substitution of an ethinyl group at carbon 17 of estradiol.A191107 Ethinylestradiol soon replaced mestranol in contraceptive pills.A191107

Ethinylestradiol was granted FDA approval on 25 June 1943.L11884

Struktur Molekul 2D

Berat 296.4034
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) A 30µg oral dose has a half life of 8.4±4.8h and a 1.2mg topical dose has a half life of 27.7±34.2h.[A191185]
Volume Distribusi A 30µg oral dose has an apparent volume of distribution of 625.3±228.7L and a 1.2mg topical dose has an apparent volume of distribution of 11745.3±15934.8L.[A191185]
Klirens (Clearance) Ethinylestradiol has an intravenous clearance of 16.47L/h, and an estimated renal clearance of approximately 2.1L/h.[A191125] A 30µg oral dose has a clearance of 58.0±19.8L/h and a 1.2mg topical dose has a clearance of 303.5±100.5L/h.[A191185]

Absorpsi

A 30µg oral dose of ethinylestradiol reaches a Cmax of 74.1±35.6pg/mL, with a Tmax of 1.5±0.5h, and an AUC of 487.4±166.6pg\*h/mL.A191185 A 1.2mg dose delivered via a patch reaches a Cmax of 28.8±10.3pg/mL, with a Tmax of 86±31h, and an AUC of3895±1423pg\*h/mL.A191185

Metabolisme

Ethinylestradiol can be glucuronidated by UGT1A1, UGT1A3, UGT1A4, UGT1A9, and UGT2B7.A190690,A191146 Ethinylestradiol is also sulfated by SULT1A1, SULT1A3, and SULT1E1.A191131,A191146 Ethinylestradiol can also be hydroxylated at positions 2, 4, 6, 7, and 16A191140,A191146 by CYP3A4, CYP3A5, CYP2C8, CYP2C9, and CYP1A2.A191125,A191146 These hydroxylated metabolites can be methylated by catechol-O-methyltransferase.A191146 The methoxy metabolites can in turn be sulfated or glucuronidated.A191146

Rute Eliminasi

Ethinylestradiol is 59.2% eliminated in the urine and bile, while 2-3% is eliminated in the feces.A191113 Over 90% of ethinylestradiol is eliminated as the unchanged parent drug.A191113

Interaksi Makanan

1 Data
  • 1. Avoid St. John's Wort. St. John's Wort may decrease the effectiveness of ethinylestradiol.

Interaksi Obat

1524 Data
Glycochenodeoxycholic Acid Ethinylestradiol may decrease the excretion rate of Glycochenodeoxycholic Acid which could result in a higher serum level.
Pravastatin Ethinylestradiol may decrease the excretion rate of Pravastatin which could result in a higher serum level.
Diethylstilbestrol Ethinylestradiol may decrease the excretion rate of Diethylstilbestrol which could result in a higher serum level.
Isradipine Ethinylestradiol may decrease the excretion rate of Isradipine which could result in a higher serum level.
Flucloxacillin Ethinylestradiol may decrease the excretion rate of Flucloxacillin which could result in a higher serum level.
Atenolol Ethinylestradiol may decrease the excretion rate of Atenolol which could result in a higher serum level.
Rosiglitazone Ethinylestradiol may decrease the excretion rate of Rosiglitazone which could result in a higher serum level.
Loratadine Ethinylestradiol may decrease the excretion rate of Loratadine which could result in a higher serum level.
Atropine Ethinylestradiol may decrease the excretion rate of Atropine which could result in a higher serum level.
Imatinib Ethinylestradiol may decrease the excretion rate of Imatinib which could result in a higher serum level.
Fluorescein Ethinylestradiol may decrease the excretion rate of Fluorescein which could result in a higher serum level.
Disulfiram Ethinylestradiol may decrease the excretion rate of Disulfiram which could result in a higher serum level.
Cefaclor Ethinylestradiol may decrease the excretion rate of Cefaclor which could result in a higher serum level.
Tinidazole Ethinylestradiol may decrease the excretion rate of Tinidazole which could result in a higher serum level.
Repaglinide Ethinylestradiol may decrease the excretion rate of Repaglinide which could result in a higher serum level.
Telmisartan Ethinylestradiol may decrease the excretion rate of Telmisartan which could result in a higher serum level.
Sulfamethoxazole Ethinylestradiol may decrease the excretion rate of Sulfamethoxazole which could result in a higher serum level.
Nitrendipine Ethinylestradiol may decrease the excretion rate of Nitrendipine which could result in a higher serum level.
Nifedipine Ethinylestradiol may decrease the excretion rate of Nifedipine which could result in a higher serum level.
Sulfinpyrazone Ethinylestradiol may decrease the excretion rate of Sulfinpyrazone which could result in a higher serum level.
Ofloxacin Ethinylestradiol may decrease the excretion rate of Ofloxacin which could result in a higher serum level.
Taurocholic acid Ethinylestradiol may decrease the excretion rate of Taurocholic acid which could result in a higher serum level.
Prasterone sulfate Ethinylestradiol may decrease the excretion rate of Prasterone sulfate which could result in a higher serum level.
Indocyanine green acid form Ethinylestradiol may decrease the excretion rate of Indocyanine green acid form which could result in a higher serum level.
Benzbromarone Ethinylestradiol may decrease the excretion rate of Benzbromarone which could result in a higher serum level.
Pilsicainide Ethinylestradiol may decrease the excretion rate of Pilsicainide which could result in a higher serum level.
Dihydroergocristine Ethinylestradiol may decrease the excretion rate of Dihydroergocristine which could result in a higher serum level.
Glycyrrhizic acid Ethinylestradiol may decrease the excretion rate of Glycyrrhizic acid which could result in a higher serum level.
Ranolazine Ethinylestradiol may decrease the excretion rate of Ranolazine which could result in a higher serum level.
Belantamab mafodotin Ethinylestradiol may decrease the excretion rate of Belantamab mafodotin which could result in a higher serum level.
Cilostazol The serum concentration of Cilostazol can be increased when it is combined with Ethinylestradiol.
Peginterferon alfa-2b The serum concentration of Ethinylestradiol can be increased when it is combined with Peginterferon alfa-2b.
Teriflunomide The serum concentration of Ethinylestradiol can be decreased when it is combined with Teriflunomide.
Leflunomide The serum concentration of Ethinylestradiol can be decreased when it is combined with Leflunomide.
Aprepitant The serum concentration of Ethinylestradiol can be decreased when it is combined with Aprepitant.
Prucalopride The serum concentration of Ethinylestradiol can be decreased when it is combined with Prucalopride.
Thalidomide Ethinylestradiol may increase the thrombogenic activities of Thalidomide.
Mifepristone The serum concentration of Ethinylestradiol can be increased when it is combined with Mifepristone.
Deferasirox The metabolism of Deferasirox can be increased when combined with Ethinylestradiol.
Zidovudine The metabolism of Ethinylestradiol can be increased when combined with Zidovudine.
Tramadol The metabolism of Tramadol can be increased when combined with Ethinylestradiol.
Indomethacin Ethinylestradiol may decrease the excretion rate of Indomethacin which could result in a higher serum level.
Minoxidil The metabolism of Minoxidil can be increased when combined with Ethinylestradiol.
Cerivastatin Ethinylestradiol may decrease the excretion rate of Cerivastatin which could result in a higher serum level.
Raloxifene The metabolism of Raloxifene can be increased when combined with Ethinylestradiol.
Diclofenac Ethinylestradiol may decrease the excretion rate of Diclofenac which could result in a higher serum level.
Labetalol The metabolism of Labetalol can be increased when combined with Ethinylestradiol.
Losartan The metabolism of Ethinylestradiol can be decreased when combined with Losartan.
Naltrexone The metabolism of Naltrexone can be increased when combined with Ethinylestradiol.
Flurbiprofen The metabolism of Flurbiprofen can be increased when combined with Ethinylestradiol.
Estradiol The metabolism of Estradiol can be increased when combined with Ethinylestradiol.
Naproxen Ethinylestradiol may decrease the excretion rate of Naproxen which could result in a higher serum level.
Propofol The metabolism of Propofol can be increased when combined with Ethinylestradiol.
Metronidazole The metabolism of Metronidazole can be increased when combined with Ethinylestradiol.
Buprenorphine The metabolism of Buprenorphine can be increased when combined with Ethinylestradiol.
Fulvestrant The metabolism of Fulvestrant can be increased when combined with Ethinylestradiol.
Ezetimibe Ethinylestradiol may decrease the excretion rate of Ezetimibe which could result in a higher serum level.
Ketoprofen The metabolism of Ketoprofen can be increased when combined with Ethinylestradiol.
Abacavir The metabolism of Abacavir can be increased when combined with Ethinylestradiol.
Ibuprofen The metabolism of Ibuprofen can be increased when combined with Ethinylestradiol.
Fluvastatin The metabolism of Fluvastatin can be increased when combined with Ethinylestradiol.
Carvedilol The metabolism of Carvedilol can be increased when combined with Ethinylestradiol.
Alvocidib The metabolism of Alvocidib can be increased when combined with Ethinylestradiol.
Indacaterol The metabolism of Indacaterol can be increased when combined with Ethinylestradiol.
Eltrombopag The metabolism of Eltrombopag can be increased when combined with Ethinylestradiol.
Bazedoxifene The metabolism of Bazedoxifene can be increased when combined with Ethinylestradiol.
Muraglitazar The metabolism of Muraglitazar can be increased when combined with Ethinylestradiol.
Gavestinel The metabolism of Gavestinel can be increased when combined with Ethinylestradiol.
Raltegravir The metabolism of Raltegravir can be increased when combined with Ethinylestradiol.
Dolutegravir The metabolism of Dolutegravir can be increased when combined with Ethinylestradiol.
Propacetamol The metabolism of Propacetamol can be increased when combined with Ethinylestradiol.
Bictegravir The metabolism of Bictegravir can be increased when combined with Ethinylestradiol.
Delafloxacin The metabolism of Delafloxacin can be increased when combined with Ethinylestradiol.
Elagolix The metabolism of Elagolix can be decreased when combined with Ethinylestradiol.
Estradiol acetate The metabolism of Estradiol acetate can be increased when combined with Ethinylestradiol.
Estradiol benzoate The metabolism of Estradiol benzoate can be increased when combined with Ethinylestradiol.
Estradiol cypionate The metabolism of Estradiol cypionate can be increased when combined with Ethinylestradiol.
Estradiol dienanthate The metabolism of Estradiol dienanthate can be increased when combined with Ethinylestradiol.
Estradiol valerate The metabolism of Estradiol valerate can be increased when combined with Ethinylestradiol.
Testosterone propionate The metabolism of Ethinylestradiol can be increased when combined with Testosterone propionate.
Lumateperone The metabolism of Lumateperone can be increased when combined with Ethinylestradiol.
Nintedanib The metabolism of Nintedanib can be increased when combined with Ethinylestradiol.
Darolutamide The metabolism of Darolutamide can be increased when combined with Ethinylestradiol.
Selumetinib The metabolism of Selumetinib can be increased when combined with Ethinylestradiol.
Cabotegravir The metabolism of Cabotegravir can be increased when combined with Ethinylestradiol.
Febuxostat The metabolism of Febuxostat can be increased when combined with Ethinylestradiol.
Ponesimod The metabolism of Ponesimod can be increased when combined with Ethinylestradiol.
Prasterone The risk or severity of adverse effects can be increased when Prasterone is combined with Ethinylestradiol.
Exemestane The therapeutic efficacy of Exemestane can be decreased when used in combination with Ethinylestradiol.
Hyaluronidase (ovine) The therapeutic efficacy of Hyaluronidase (ovine) can be decreased when used in combination with Ethinylestradiol.
Hyaluronidase (human recombinant) The therapeutic efficacy of Hyaluronidase (human recombinant) can be decreased when used in combination with Ethinylestradiol.
Hyaluronidase The therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Ethinylestradiol.
Lenalidomide Ethinylestradiol may increase the thrombogenic activities of Lenalidomide.
Ospemifene The risk or severity of adverse effects can be increased when Ethinylestradiol is combined with Ospemifene.
Ropinirole Ethinylestradiol may increase the excretion rate of Ropinirole which could result in a lower serum level and potentially a reduction in efficacy.
Colesevelam Colesevelam can cause a decrease in the absorption of Ethinylestradiol resulting in a reduced serum concentration and potentially a decrease in efficacy.
Rufinamide The therapeutic efficacy of Ethinylestradiol can be decreased when used in combination with Rufinamide.
Abiraterone The serum concentration of Ethinylestradiol can be increased when it is combined with Abiraterone.
Glycocholic acid The therapeutic efficacy of Glycocholic acid can be decreased when used in combination with Ethinylestradiol.
Deoxycholic acid The therapeutic efficacy of Deoxycholic acid can be decreased when used in combination with Ethinylestradiol.

Target Protein

Estrogen receptor ESR1
Nuclear receptor subfamily 1 group I member 2 NR1I2

Referensi & Sumber

Synthesis reference: Andreas Sachse, "Method of female hormonal contraception using a fixed extended cycle hormonal preparation containing dienogest and ethinyl estradiol." U.S. Patent US20060079491, issued April 13, 2006.
Artikel (PubMed)
  • PMID: 21091163
    Dhont M: History of oral contraception. Eur J Contracept Reprod Health Care. 2010 Dec;15 Suppl 2:S12-8. doi: 10.3109/13625187.2010.513071.
  • PMID: 5802625
    Cargill DI, Steinetz BG, Gosnell E, Beach VL, Meli A, Fujimoto GI, Reynolds BM: Fate of ingested radiolabeled ethynylestradiol and its 3-cyclopentyl ether in patients with bile fistulas. J Clin Endocrinol Metab. 1969 Aug;29(8):1051-61. doi: 10.1210/jcem-29-8-1051.
  • PMID: 8474433
    Ebner T, Remmel RP, Burchell B: Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol. 1993 Apr;43(4):649-54.
  • PMID: 29637542
    Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27.
  • PMID: 4214831
    Bolt HM, Kappus H, Kasbohrer R: Metabolism of 17 alpha-ethinylestradiol by human liver microsomes in vitro: aromatic hydroxylation and irreversible protein binding of metabolites. J Clin Endocrinol Metab. 1974 Dec;39(6):1072-80. doi: 10.1210/jcem-39-6-1072.
  • PMID: 15483196
    Schrag ML, Cui D, Rushmore TH, Shou M, Ma B, Rodrigues AD: Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol. Drug Metab Dispos. 2004 Nov;32(11):1299-303. doi: 10.1124/dmd.32.11..
  • PMID: 28579309
    Stegeman BH, Vos HL, Helmerhorst FM, Rosendaal FR, Reitsma PH, van Hylckama Vlieg A: Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk. Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019. Epub 2017 Jun 1.
  • PMID: 2308344
    Kuhnz W, Pfeffer M, al-Yacoub G: Protein binding of the contraceptive steroids gestodene, 3-keto-desogestrel and ethinylestradiol in human serum. J Steroid Biochem. 1990 Feb;35(2):313-8. doi: 10.1016/0022-4731(90)90290-9.
Menampilkan 8 dari 13 artikel.

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