QuickView for Ethinyl Estradiol (compound)

Summary
General Info

PubChem

PubChem Compound 11865431

Name:	Ethinyl Estradiol
PubChem Compound ID:	11865431
Description:	A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.
Molecular formula:	C₂₀H₂₄O₂
Molecular weight:	296.403 g/mol
Synonyms:	ZINC03830791

DrugBank

Identification

Name:	Ethinyl Estradiol
Name (isomeric):	DB00977
Drug Type:	small molecule
Description:	A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.
Synonyms:	Ethynylestradiol; EE; Ethinylestradiolum [INN-Latin]; Ethinyloestradiol; Ethinyl-Oestranol; 17 alpha-Ethynylestradiol; 17 alpha-Ethinylestradiol; Ethinylestriol; EO; Aethinyoestradiol [German]. show more » Ethynylestradiol; EE; Ethinylestradiolum [INN-Latin]; Ethinyloestradiol; Ethinyl-Oestranol; 17 alpha-Ethynylestradiol; 17 alpha-Ethinylestradiol; Ethinylestriol; EO; Aethinyoestradiol [German]; Ethynyloestradiol; Ethynyl estradiol; 17 alpha-Ethynyloestradiol; Aethinyloestradiolum; Etinilestradiol [INN-Spanish] show less «
Brand:	Etivex, Ortho-Cyclen, Halodrin, Amenoron, Microfollin, Dicromil, Ethidol, Dyloform, Primogyn, Eticyclin, Spanestrin, Gynolett, Progynon M, Etinestrol, Ethinoral, Estoral, Marvelon, Cyclosa, Progynon C, Estigyn, Eticylol, Diogyn E, Prosexol, Neo-Estrone, Ethy 11, Ginestrene, Follicoral, Oradiol, Estopherol, Primogyn C, Estorals, Eticyclol, Diognat-E, Etinoestryl, Eston-E, Nogest-S, Orestralyn, Novestrol, Ertonyl, Ylestrol, Esteed, Amenorone, Etistradiol, Etinestryl, Mercilon, Linoral, Orestrayln, Varnoline, Oviol, Inestra, Diprol, Menolyn, Diogyn-E, Primogyn M, Anovlar, Kolpolyn
Brand name mixture:	Triphasil 28 Tab(Ethinyl Estradiol + Levonorgestrel), Yasmin 28(Drospirenone + Ethinyl Estradiol), Synphasic 21 Tablets(Ethinyl Estradiol + Norethindrone), Cyclen(Ethinyl Estradiol + Norgestimate), Minestrin 1/20 28(Ethinyl Estradiol + Norethindrone Acetate), Ortho Tablets (0.5/35, 1/35, 10/11, 7/7/7)(Ethinyl Estradiol + Norethindrone), Evra(Eth... show more » Triphasil 28 Tab(Ethinyl Estradiol + Levonorgestrel), Yasmin 28(Drospirenone + Ethinyl Estradiol), Synphasic 21 Tablets(Ethinyl Estradiol + Norethindrone), Cyclen(Ethinyl Estradiol + Norgestimate), Minestrin 1/20 28(Ethinyl Estradiol + Norethindrone Acetate), Ortho Tablets (0.5/35, 1/35, 10/11, 7/7/7)(Ethinyl Estradiol + Norethindrone), Evra(Ethinyl Estradiol + Norelgestromin), Alesse 21 Tablets(Ethinyl Estradiol + Levonorgestrel), Brevicon(Ethinyl Estradiol + Norethindrone), Synphasic-28 Tablets(Ethinyl Estradiol + Norethindrone), Neo Mens Tab(Ethinyl Estradiol + Ethisterone), Tri-Cyclen Tablets - 21-Day(Ethinyl Estradiol + Norgestimate), Diane-35(Cyproterone Acetate + Ethinyl Estradiol), Demulen 30(Ethinyl Estradiol + Ethynodiol Diacetate), Min-Ovral 21(Ethinyl Estradiol + Levonorgestrel), Geri Tabs(Calcium (Calcium Phosphate (Dibasic)) + Copper Sulfate + Dl-Methionine + Ethinyl Estradiol + Folic Acid + Iodine + Iron Peptonized + Magnesium Oxide + Manganese Sulfate + Methyltestosterone + Nicotinamide + Phosphorus (Calcium Phosphate (Dibasic)) + Pyridoxine Hydrochloride + Thiamine Hydrochloride + Thyroid + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D + Vitamin E), Femhrt 1/5(Ethinyl Estradiol + Norethindrone Acetate), Triphasil 28(Ethinyl Estradiol + Levonorgestrel), Ortho-Cept Tablets(Desogestrel + Ethinyl Estradiol), Loestrin 1.5/30 21day Pak(Ethinyl Estradiol + Norethindrone Acetate), Geri Bons Tab(Calcium (Calcium Phosphate (Dibasic)) + Copper + Dl-Methionine + Ethinyl Estradiol + Fatty Acids + Folic Acid + Iodine + Iron Peptonized + Magnesium + Manganese + Methyltestosterone + Nicotinamide + Phosphorus (Calcium Phosphate (Dibasic)) + Pyridoxine Hydrochloride + Thiamine Hydrochloride + Thyroid + Vitamin a + Vitamin B12 + Vitamin B2 + Vitamin D + Vitamin E), Minestrin 1/20 21(Ethinyl Estradiol + Norethindrone Acetate), Triquilar 21 Tab(Ethinyl Estradiol + Levonorgestrel), Ovral 21 Tablets(Ethinyl Estradiol + Norgestrel (Norgestrel)), Synphasic 28 Tablets(Ethinyl Estradiol + Norethindrone), Alesse 28 Tablets(Ethinyl Estradiol + Levonorgestrel), Marvelon 28 Tab(Desogestrel + Ethinyl Estradiol), Tri-Cyclen Tablets - 28-Day(Ethinyl Estradiol + Norgestimate), Ovral 28tab(Ethinyl Estradiol + Norgestrel), Ovral 21 Tab(Ethinyl Estradiol + Norgestrel (Norgestrel)), Tri-Cyclen Lo(Ethinyl Estradiol + Norgestimate), Loestrin 1.5/30 28day Pack(Ethinyl Estradiol + Norethindrone Acetate), Yasmin 21(Drospirenone + Ethinyl Estradiol), Lo-Femenal 21 Tablets(Ethinyl Estradiol + Norgestrel), Select 1/35(Ethinyl Estradiol + Norethindrone), Min-Ovral 21 Tab(Ethinyl Estradiol + Levonorgestrel), Ovral 28 Tablets(Ethinyl Estradiol + Norgestrel (Norgestrel)), Min-Ovral 28 Tab(Ethinyl Estradiol + Levonorgestrel), Triquilar 28 Tab(Ethinyl Estradiol + Levonorgestrel), Nuvaring(Ethinyl Estradiol + Etonogestrel), Preven Tablets(Ethinyl Estradiol + Levonorgestrel), Demulen 50(Ethinyl Estradiol + Ethynodiol Diacetate), Triphasil 21(Ethinyl Estradiol + Levonorgestrel), Marvelon 21 Tab(Desogestrel + Ethinyl Estradiol), Triphasil 21 Tab(Ethinyl Estradiol + Levonorgestrel), Min-Ovral 28(Ethinyl Estradiol + Levonorgestrel) show less «
Category:	Estrogens
CAS number:	57-63-6

Pharmacology

Indication:	For treatment of moderate to severe vasomotor symptoms associated with the menopause, female hypogonadism, prostatic carcinoma-palliative therapy of advanced disease, breast cancer, as an oral contraceptive, and as emergency contraceptive.
Pharmacology:	Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol. It is one of two estrogens currently used in oral contraceptive pills. The other, mestranol, is converted to ethinyl estradiol before it is biologically active. Ethinyl estradiol and norethindrone are used together as an oral contraceptive agent.
Mechanism of Action:	Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-st... show more » Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. This cascade is initiated by initially binding to the estrogen receptors. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). show less «
Absorption:	Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
Protein binding:	97%
Biotransformation:	Hepatic. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.
Half Life:	36 +/- 13 hours
Toxicity:	Oral, mouse LD₅₀: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Dicloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Prednisone	The estrogenic agent, ethinyl estradiol, may increase the effect of corticosteroid, prednisone.
Hetacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
St. John's Wort	St. John's Wort could reduce the contraceptive effect
Meticillin	This anti-infectious agent could decrease the effect of the oral contraceptive

Dicloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Prednisone	The estrogenic agent, ethinyl estradiol, may increase the effect of corticosteroid, prednisone.
Hetacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
St. John's Wort	St. John's Wort could reduce the contraceptive effect
Meticillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Rolitetracycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Thiopental	Thiopental may decrease the effect of Ethinyl estradiol. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
Amobarbital	This product may cause a slight decrease of contraceptive effect
Minocycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Phenytoin	This product may cause a slight decrease of contraceptive effect
Azlocillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Dicumarol	Increased thrombotic risk due to estrogen
Tacrolimus	Ethinyl estradiol may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Ethinyl estradiol therapy is initiated, discontinued or altered.
Ticarcillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Oxytetracycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Fosphenytoin	This product may cause a slight decrease of contraceptive effect
Oxcarbazepine	Oxcarbazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied upon during concomitant therapy with oxcarbazepine.
Acenocoumarol	Increased thrombotic risk due to estrogen
Aprepitant	Aprepitant could decrease the effect of the oral contraceptive
Oxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Carbamazepine	Carbamazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with carbamazepine.
Ampicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Cloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Clavulanate	This anti-infectious agent could decrease the effect of the oral contraceptive
Cyclacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Heptabarbital	This product may cause a slight decrease of contraceptive effect
Rifapentine	This product may cause a slight decrease of contraceptive effect
Pentobarbital	This product may cause a slight decrease of contraceptive effect
Prednisolone	The estrogenic agent, ethinyl estradiol, may increase the effect of the corticosteroid, prednisolone.
Amprenavir	Ritonavir could decrease the contraceptive efficacy
Butalbital	This product may cause a slight decrease of contraceptive effect
Ketoconazole	This anti-infectious agent could decrease the effect of the oral contraceptive
Warfarin	Ethinyl estradiol may alter the anticoagulant effect of warfarin. Concomitant therapy should be avoided. Monitor for changes in coagulation status if ethinyl estradiol is initiated, discontinued or dose changed.
Mephenytoin	This product may cause a slight decrease of contraceptive effect
Talbutal	This product may cause a slight decrease of contraceptive effect
Oxtriphylline	The contraceptive increases the effect and toxicity of theophylline
Butabarbital	This product may cause a slight decrease of contraceptive effect
Rifampin	This product may cause a slight decrease of contraceptive effect
Aprobarbital	This product may cause a slight decrease of contraceptive effect
Hexobarbital	This product may cause a slight decrease of contraceptive effect
Amoxicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Troglitazone	Possible loss of contracepitve effect
Modafinil	Modafinil may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied on during concomitant therapy with modafinil.
Theophylline	The contraceptive increases the effect and toxicity of theophylline
Dyphylline	The contraceptive increases the effect and toxicity of theophylline
Griseofulvin	This product may cause a slight decrease of contraceptive effect
Methohexital	This product may cause a slight decrease of contraceptive effect
Ursodeoxycholic acid	Estrogens decreases the effect of ursodiol
Phenobarbital	This product may cause a slight decrease of contraceptive effect
Bosentan	Bosentan may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with bosentan.
Aztreonam	This anti-infectious agent could decrease the effect of the oral contraceptive
Nelfinavir	Ritonavir could decrease the contraceptive efficacy
Piperacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Rifabutin	Rifabutin may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied on alone during concomitant therapy with rifabutin.
Butethal	This product may cause a slight decrease of contraceptive effect
Ritonavir	Ritonavir could decrease the contraceptive efficacy
Tizanidine	Ethinyl estradiol may increase the serum concentration of tizanidine. Monitor for changes in the therapeutic and adverse effects of tizanidine if ethinyl estradiol is initiated, discontinued or dose changed.
Colesevelam	Bile Acid Sequestrants may decrease the serum concentration of Contraceptives (Estrogens). Administer estrogen-based oral contraceptives at least 1-4 hours prior to or 4-6 hours after administration of a bile acid sequestrant. Consider alternatives in order to avoid this combination when possible, due to the risk for impaired contraceptive effectiveness. Ethinyl estradiol patches and vaginal rings may also be somewhat impacted by this interaction, though the extent and significance of such an interaction is uncertain.
Topiramate	Topiramate may decrease the effect of the oral contraceptive, Ethinyl estradiol. An alternate form of contraception should be used during concomitant therapy.
Cyclosporine	The contraceptive increases the effect and toxicity of cyclosporine
Anisindione	Increased thrombotic risk due to estrogen
Lamotrigine	The oral contraceptive decreases the effect of lamotrigine
Tazobactam	This anti-infectious agent could decrease the effect of the oral contraceptive
Doxycycline	Doxycycline may decrease the contraceptive effect of ethinyl estradiol.
Artemether	Artemether may decrease the effectiveness of ethinyl estradiol by increasing its metabolism via CYP3A4. Consider an alternate non-hormonal means of contraception during artemether therapy.
Nafcillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Demeclocycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Aminophylline	The contraceptive increases the effect and toxicity of theophylline
Etoricoxib	Etoricoxib may increase the levels of ethinyl estradiol.
Methacycline	This anti-infectious agent could decrease the effect of the oral contraceptive
Methylphenobarbital	This product may cause a slight decrease of contraceptive effect
Bacampicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Pivampicillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Flucloxacillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Tretinoin	Oral Tretinoin may decrease the effect of the oral contraceptive, Ethinyl Estradiol. An alternate form of contraception should be used during concomitant therapy.
Primidone	This product may cause a slight decrease of contraceptive effect
Raloxifene	Association not recommended
Mezlocillin	This anti-infectious agent could decrease the effect of the oral contraceptive
Tipranavir	Tipranavir, co-administered with Ritonavir, decreases Ethinyl estradiol concentrations. Ethinyl estradiol may increase the adverse dermatological effects (i.e. skin rash) of Tipranavir. Use an alternate form of contraception or monitor for estrogen deficiency if Ethinyl estradiol is used for hormone replacement therapy.
Ethotoin	This product may cause a slight decrease of contraceptive effect
Secobarbital	This product may cause a slight decrease of contraceptive effect
Tetracycline	This anti-infectious agent could decrease the effect of the oral contraceptive

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Targets

Estrogen receptor

Orphan nuclear receptor PXR

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2C8

Transporters

Bile salt export pump

Sodium/bile acid cotransporter

Canalicular multispecific organic anion transporter 1

Multidrug resistance protein 1