Tìm theo
Ethinyl Estradiol
Các tên gọi khác (17 ) :
  • 17 alpha-Ethinylestradiol
  • 17 alpha-Ethynylestradiol
  • 17 alpha-Ethynyloestradiol
  • 17-ethinyl-3,17-estradiol
  • 17-ethinyl-3,17-oestradiol
  • 17-ethinylestradiol
  • 17alpha-Ethinyl estradiol
  • 17α-ethynylestradiol
  • Ethinyl-Oestranol
  • Ethinylestradiol
  • Ethinylestradiolum
  • Ethinylestriol
  • Ethinyloestradiol
  • Ethynyl estradiol
  • Ethynylestradiol
  • Ethynyloestradiol
  • Etinilestradiol
Hormon, Nội tiết tố
Thuốc Gốc
Small Molecule
CAS: 57-63-6
ĐG : Amerisource Health Services Corp. , http://www.amerisourcebergen.com
CTHH: C20H24O2
PTK: 296.4034
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 [PubChem]. Ethinyl estradiol is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Tri-Cyclen, Triphasil, and Yasmin. The FDA label includes a black box warning that states that combination oral contraceptives should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C20H24O2
Phân tử khối
296.4034
Monoisotopic mass
296.177630012
InChI
InChI=1/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/s2
InChI Key
InChIKey=BFPYWIDHMRZLRN-RHKZOZTBNA-N
IUPAC Name
(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol
Traditional IUPAC Name
ethinyl estradiol
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
Độ tan chảy
142-144
Độ hòa tan
11.3 mg/L (at 27 °C)
logP
3.67
logS
-4.3
pKa (strongest acidic)
10.33
pKa (Strongest Basic)
-1.7
PSA
40.46 Å2
Refractivity
87.37 m3·mol-1
Polarizability
34.53 Å3
Rotatable Bond Count
0
H Bond Acceptor Count
2
H Bond Donor Count
2
Physiological Charge
0
Number of Rings
4
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : 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 [PubChem]. Ethinyl estradiol is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Tri-Cyclen, Triphasil, and Yasmin. The FDA label includes a black box warning that states that combination oral contraceptives should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects. 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).
Dược Động Học :
▧ Absorption :
Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
▧ Protein binding :
97%
▧ Metabolism :
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
Độc Tính : Oral, mouse LD50: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females. The FDA label includes a black box warning that states that combination oral contraceptives with ethinyl estradiol should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
Chỉ Định : 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.
Tương Tác Thuốc :
  • Acenocoumarol Increased thrombotic risk due to estrogen
  • Aminophylline The contraceptive increases the effect and toxicity of theophylline
  • Amobarbital This product may cause a slight decrease of contraceptive effect
  • Amoxicillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Ampicillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Amprenavir Ritonavir could decrease the contraceptive efficacy
  • Anisindione Increased thrombotic risk due to estrogen
  • Aprepitant Aprepitant could decrease the effect of the oral contraceptive
  • Aprobarbital This product may cause a slight decrease of contraceptive effect
  • 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.
  • Azlocillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Aztreonam This anti-infectious agent could decrease the effect of the oral contraceptive
  • Bacampicillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Bendamustine Increases levels of bendamustine by decreasing metabolism. Ethinyl Estradiol is a CYP1A2 inhibitor and concurrent administration may result in elevated plasma concentrations of bendamustine.
  • Bosentan Bosentan may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with bosentan.
  • Butabarbital This product may cause a slight decrease of contraceptive effect
  • Butalbital This product may cause a slight decrease of contraceptive effect
  • Butethal This product may cause a slight decrease of contraceptive effect
  • Carbamazepine Carbamazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be relied on alone during concomitant therapy with carbamazepine.
  • Clavulanate 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
  • 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.
  • Cyclacillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Cyclosporine The contraceptive increases the effect and toxicity of cyclosporine
  • Demeclocycline 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
  • Dicoumarol Increased thrombotic risk due to estrogen
  • Doxycycline Doxycycline may decrease the contraceptive effect of ethinyl estradiol.
  • Dyphylline The contraceptive increases the effect and toxicity of theophylline
  • Eltrombopag Affects hepatic CYP1A2 metabolism, increases Eltrombopag level or affect.
  • Ethotoin This product may cause a slight decrease of contraceptive effect
  • Etoricoxib Etoricoxib may increase the levels of ethinyl estradiol.
  • Flucloxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Fosphenytoin This product may cause a slight decrease of contraceptive effect
  • Griseofulvin This product may cause a slight decrease of contraceptive effect
  • Heptabarbital This product may cause a slight decrease of contraceptive effect
  • Hetacillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Hexobarbital This product may cause a slight decrease of contraceptive effect
  • Ketoconazole This anti-infectious agent could decrease the effect of the oral contraceptive
  • Lamotrigine The oral contraceptive decreases the effect of lamotrigine
  • Mephenytoin This product may cause a slight decrease of contraceptive effect
  • Methacycline This anti-infectious agent could decrease the effect of the oral contraceptive
  • Methohexital This product may cause a slight decrease of contraceptive effect
  • Methylphenobarbital This product may cause a slight decrease of contraceptive effect
  • Meticillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Mezlocillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Minocycline This anti-infectious agent could decrease the effect of the oral contraceptive
  • Modafinil Modafinil may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied on during concomitant therapy with modafinil.
  • Nafcillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Nelfinavir Ritonavir could decrease the contraceptive efficacy
  • Oxacillin This anti-infectious agent could decrease the effect of the oral contraceptive
  • Oxcarbazepine Oxcarbazepine may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied upon during concomitant therapy with oxcarbazepine.
  • Oxtriphylline The contraceptive increases the effect and toxicity of theophylline
  • Oxytetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
  • Pentobarbital This product may cause a slight decrease of contraceptive effect
  • Phenobarbital This product may cause a slight decrease of contraceptive effect
  • Phenytoin This product may cause a slight decrease of contraceptive effect
  • Piperacillin 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
  • Prednisolone The estrogenic agent, ethinyl estradiol, may increase the effect of the corticosteroid, prednisolone.
  • Prednisone The estrogenic agent, ethinyl estradiol, may increase the effect of corticosteroid, prednisone.
  • Primidone This product may cause a slight decrease of contraceptive effect
  • Raloxifene Association not recommended
  • Rifabutin Rifabutin may decrease the contraceptive effect of ethinyl estradiol. Hormonal contraception should not be solely relied on alone during concomitant therapy with rifabutin.
  • Rifampicin This product may cause a slight decrease of contraceptive effect
  • Rifapentine This product may cause a slight decrease of contraceptive effect
  • Ritonavir Ritonavir could decrease the contraceptive efficacy
  • Rolitetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
  • Rufinamide Rufinamide decreases plasma concentrations of ethinyl estradiol, thus consider therapy modification
  • Secobarbital This product may cause a slight decrease of contraceptive effect
  • St. John's Wort St. John's Wort could reduce the contraceptive effect
  • 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.
  • Talbutal This product may cause a slight decrease of contraceptive effect
  • Tazobactam This anti-infectious agent could decrease the effect of the oral contraceptive
  • Tetracycline This anti-infectious agent could decrease the effect of the oral contraceptive
  • Theophylline The contraceptive increases the effect and toxicity of theophylline
  • Thiopental Thiopental may decrease the effect of Ethinyl estradiol. Contraceptive failure may occur. Alternative nonhomomonal contraception should be used during concomitant therapy.
  • Ticarcillin 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.
  • 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.
  • Topiramate Topiramate may decrease the effect of the oral contraceptive, Ethinyl estradiol. An alternate form of contraception should be used during concomitant therapy.
  • Tretinoin Oral Tretinoin may decrease the effect of the oral contraceptive, Ethinyl Estradiol. An alternate form of contraception should be used during concomitant therapy.
  • Troglitazone Possible loss of contracepitve effect
  • Ursodeoxycholic acid Estrogens decreases the effect of ursodiol
  • 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.
Liều Lượng & Cách Dùng : Cream - Intravaginal
Insert, extended release - Transdermal
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Schering
    Sản phẩm biệt dược : Estinyl
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00977
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07534
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00554
PharmGKB
http://www.pharmgkb.org/drug/PA449527
Wikipedia
http://en.wikipedia.org/wiki/Ethinylestradiol
RxList
http://www.rxlist.com/cgi/generic/estinyl.htm
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