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Substance Name: Ethinylestradiol [INN:BAN:JAN]
RN: 57-63-6
UNII: 423D2T571U
InChIKey: BFPYWIDHMRZLRN-SLHNCBLASA-N

Note

  • 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

  • C20-H24-O2

Molecular Weight

  • 296.4076
 

Classification Codes

Classification Codes

  • Drug / Therapeutic Agent
  • Estrogen
  • Estrogens
  • Hormone
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Reasonably Anticipated to be a Carcinogen

Names and Synonyms

Results Name

  • Ethinylestradiol [INN:BAN:JAN]

Name of Substance

  • Ethinyl Estradiol [USP]

MeSH Heading

  • Ethinyl estradiol

Synonyms

  • (17-alpha)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17,diol
  • (17alpha)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol
  • 17-alpha-Ethinyl-17-beta-estradiol
  • 17-alpha-Ethinyl-3,17-dihydroxy-delta(sup 1,3,5)-estratriene
  • 17-alpha-Ethinyl-delta(sup 1,3,5(10))oestratriene-3,17-beta-diol
  • 17-alpha-Ethinylestra-1,3,5(10)-triene-3,17-beta-diol
  • 17-alpha-Ethinyloestra-1,3,5(10)-triene-3,17-beta-diol
  • 17-alpha-Ethynyl-1,3,5(10)-estratriene-3,17-beta-diol
  • 17-alpha-Ethynyl-1,3,5(10)-oestratriene-3,17-beta-diol
  • 17-alpha-Ethynyl-1,3,5-oestratriene-3,17-beta-diol
  • 17-alpha-Ethynyl-17-beta-oestradiol
  • 17-alpha-Ethynylestradiol
  • 17-alpha-Ethynylestradiol-17-beta
  • 17-Ethinyl-3,17-estradiol
  • 17-Ethinyl-3,17-oestradiol
  • 17-Ethinylestradiol
  • 17-Ethynyl-3,17-dihydroxy-1,3,5-oestratriene
  • 17-Ethynylestra-1,3,5(10)-triene-3,17beta-diol
  • 17-Ethynylestradiol
  • 17-Ethynyloestradiol
  • 17alpha-Ethinyl-1,3,5(10)-estratriene-3,17-diol
  • 17alpha-Ethinyl-17beta-estradiol
  • 17alpha-Ethinyl-3,17-dihydroxy-delta(sup1,3,5)-estratriene
  • 17alpha-ethinyl-3,17-dihydroxy-delta(sup1,3,5)oestratriene
  • 17alpha-ethinyl-delta(sup1,3,5(10))oestratriene-3,17-beta -diol
  • 17alpha-ethinylestra-1,3,5(10)-triene-3,17beta-diol
  • 17alpha-Ethinylestradiol
  • 17alpha-Ethinylestradiol-17beta
  • 17alpha-ethinyloestra-1,3,5(10)-triene-3,17beta-diol
  • 17alpha-Ethynylestradiol
  • 17alpha-Ethynyloestradiol
  • 17alpha-Ethynyloestradiol-17beta; 17beta-Estradiol, 17-ethynyl-
  • 19-Nor-17-alpha-pregna-1,3,5(10)-triene-20-yne-3,17-diol
  • 19-Nor-17alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol
  • 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-estratriene
  • 3,17-beta-Dihydroxy-17-alpha-ethynyl-1,3,5(10)-oestratriene
  • 3,17beta-Dihydroxy-17alpha-ethynyl-1,3,5(10)-estratriene
  • 3,17beta-Dihydroxy-17alpha-ethynyl-1,3,5(10)-oestratriene
  • 4-06-00-06877 (Beilstein Handbook Reference)
  • Aethinyloestradiolum
  • Aethinyoestradiol
  • Aethinyoestradiol [German]
  • AI3-52941
  • Amenoron
  • Amenorone
  • BRN 2419975
  • CCRIS 286
  • Certostat
  • Chee-O-Gen
  • Chee-O-Genf
  • Diogyn E
  • Diprol
  • Dyloform
  • EE
  • EE(sub 2)
  • EE2
  • EINECS 200-342-2
  • EO
  • Ertonyl
  • Esteed
  • Estigyn
  • Estinyl
  • Eston-E
  • Estoral
  • Estoral (orion)
  • Estoral (VAN)
  • Estorals
  • Estra-1,3,5(10)-triene-3,17-beta-diol, 17-alpha-ethynyl-
  • Estra-1,3,5(10)-triene-3,17beta-diol, 17alpha-ethynyl-
  • Estradiol, 17-ethynyl-
  • Ethidol
  • Ethinoral
  • Ethinyl E2
  • Ethinyl estradiol
  • Ethinyl-oestranol
  • Ethinylestradiol
  • Ethinylestradiol [INN:BAN:JAN]
  • Ethinylestradiolum
  • Ethinylestradiolum [INN-Latin]
  • Ethinyloestradiol
  • Ethynylestradiol
  • Ethynyloestradiol
  • Eticyclin
  • Eticyclol
  • Etinestrol
  • Etinestryl
  • Etinilestradiol
  • Etinilestradiol [INN-Spanish]
  • Etinilestradiolo
  • Etinilestradiolo [DCIT]
  • Etinoestryl
  • Etistradiol
  • Feminone
  • Follicoral
  • Ginestrene
  • HSDB 3587
  • Inestra
  • Linoral
  • Lynoral
  • Menolyn
  • Microfollin
  • Neo-Estrone
  • Nogest-S
  • Novestrol
  • NSC-10973
  • Oradiol
  • Orestralyn
  • Palonyl
  • Perovex
  • Primogyn
  • Primogyn C
  • Primogyn M
  • Progynon C
  • Spanestrin
  • UNII-423D2T571U

Systematic Names

  • 19-Nor-17-alpha-pregna-1,3,5(10)-trien-20-yne-3,17-diol
  • 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17alpha)-
  • Ethinylestradiol

Superlist Names

  • 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol, (17alpha)-
  • Ethinyl estradiol
  • Ethinyloestradiol
  • Ethinyloestradiol [Steroidal oestrogens]

Mixture Names

  • Brevicon
  • Demulen
  • Desogen
  • Estopherol
  • Halodrin
  • Levlen
  • Lo/Ovral
  • Loestrin
  • Modicon
  • Nordette
  • Norethin 1/35 E
  • Norlestrin
  • Ortho Evra
  • Ortho-Cyclen
  • Ortho-Novum
  • Ovcon
  • Ovral
  • Seasonale
  • Seasonique
  • Tri-Levlen
  • Triphasil

Registry Numbers

CAS Registry Number

  • 57-63-6

FDA UNII

  • 423D2T571U

Other Registry Numbers

  • 1050678-65-3
  • 406932-93-2
  • 77538-56-8

System Generated Number

  • 0000057636

Structure Descriptors

InChI

1S/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+/m1/s1

InChIKey

BFPYWIDHMRZLRN-SLHNCBLASA-N

Smiles

C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@]2(C#C)O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
mouse LD50 oral 950mg/kg (950mg/kg)   Drugs in Japan Vol. -, Pg. 222, 1995.
mouse LD50 subcutaneous > 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: HEMORRHAGE		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
rat LD50 intraperitoneal 471mg/kg (471mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BEHAVIORAL: ATAXIA		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
rat LD50 oral 960mg/kg (960mg/kg)   Drugs in Japan Vol. -, Pg. 222, 1995.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg) BLOOD: HEMORRHAGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
women TDLo oral 21mg/kg/21D-I (21mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Lancet. Vol. 1, Pg. 1479, 1973.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 183 deg C   EXP
log P (octanol-water) 3.67 (none)   EXP
Water Solubility 11.3 mg/L 27 EXP
Vapor Pressure 2.67E-09 mm Hg 25 EST
Henry's Law Constant 7.94E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.25E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.