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Ethynyl estradiol

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Name

Ethynyl estradiol

EINECS 200-342-2
CAS No. 57-63-6 Density 1.21 g/cm3
PSA 40.46000 LogP 3.61260
Solubility ethanol: 50 mg/mL, clear, slightly yellow Melting Point 182-183 °C(lit.)
Formula C20H24O2 Boiling Point 457.2 °C at 760 mmHg
Molecular Weight 296.409 Flash Point 211.2 °C
Transport Information N/A Appearance Off-White to Light-Yellow Crystalline Powder
Safety 53-36/37/39-45 Risk Codes 45-22
Molecular Structure Molecular Structure of 57-63-6 (Ethynyl estradiol) Hazard Symbols ToxicT
Synonyms

19-Nor-17a-pregna-1,3,5(10)-trien-20-yne-3,17-diol(6CI,7CI,8CI);17-Ethinyl-3,17-estradiol;17-Ethinylestradiol;17-Ethynylestra-1,3,5(10)-triene-3,17b-diol;17a-Ethinyl-3,17-dihydroxy-D1,3,5-estratriene;17a-Ethynylestra-3,17b-diol;17a-Ethynylestradiol;19-Nor-17a-pregna-1,3,5(10)-trien-20-yne-3,17b-diol;Amenoron;Chee-O-Gen;Esteed;Estoral;Estorals;Estradiol, 17-ethynyl-;Ethidol;Ethinoral;Ethynylestradiol;Ethynyloestradiol;Eticyclin;Eticyclol;Follicoral;Ginestrene;Linoral;Lynoral;Microfollin;NSC 10973;Oradiol;Orestralyn;Primogyn C;Progynon C;

Article Data 43

Ethynyl estradiol Synthetic route

68-22-4

norethisterone

57-63-6

ethinyl estradiol

Conditions
ConditionsYield
With copper(ll) bromide In acetonitrile for 16h; Ambient temperature;79%
homogenates of human adult liver;
With Cephalosporium aphidicola (IMI 68689) In dimethyl sulfoxide at 29℃; for 192h;164 mg
53-16-7

Estrone

1111-63-3, 115570-71-3

potassium acetylide

57-63-6

ethinyl estradiol

53-16-7

Estrone

4301-14-8

acetylenemagnesium bromide

57-63-6

ethinyl estradiol

Ethynyl estradiol Chemical Properties


IUPAC Name: (8R,9S,13S,14S,17R)-17-Ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
Molecular Weight: 296.40336 [g/mol]
Molecular Formula: C20H24O2
XLogP3: 3.7
H-Bond Donor: 2
H-Bond Acceptor: 2 
EINECS: 200-342-2
Product Categories: Alcohols and Derivatives; Steroids; Acetylenes; Biochemistry; Functionalized Acetylenes; Hydroxysteroids; Intermediates & Fine Chemicals; Metabolites & Impurities; Pharmaceuticals 
Refractive index: -30 ° (C=0.4, Pyridine)
Solubility: ethanol: 50 mg/mL, clear, slightly yellow 
Index of Refraction: 1.623
Molar Refractivity: 86.26 cm3
Molar Volume: 244.4 cm3
Surface Tension: 57.2 dyne/cm
Density: 1.21 g/cm3
Flash Point: 211.2 °C
Enthalpy of Vaporization: 75.58 kJ/mol
Boiling Point: 457.2 °C at 760 mmHg
Vapour Pressure: 3.74E-09 mmHg at 25 °C
Appearance: Off-White to Light-Yellow Crystalline Powder
Melting Point: 182-183 °C(lit.)
Classification Code of Ethynyl estradiol (CAS NO.57-63-6): Drug / Therapeutic Agent; Estrogen; Estrogens; Hormone; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Mutation data; Reproductive Effect; Tumor data

Ethynyl estradiol History

The first orally active semisynthetic steroidal estrogen, Ethynyl estradiol (CAS NO.57-63-6), the 17alpha-ethynyl analog of estradiol, was synthesized in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at Schering AG in Berlin. It was approved by the FDA in the U.S. on June 25, 1943 and marketed by Schering as Estinyl. The FDA withdrew approval of Estinyl effective June 4, 2004 at the request of Schering, who had discontinued marketing Estinyl.

Ethynyl estradiol Uses

 Ethynyl estradiol (CAS NO.57-63-6) is used as a female hormone class medicine. It is a synthetic steroid with high oral estrogenic potency.

Ethynyl estradiol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 250mg/kg (250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
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

BEHAVIORAL: ATAXIA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
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) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BLOOD: HEMORRHAGE
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 18, Pg. 2583, 1990.
women TDLo oral 21mg/kg/21D-I (21mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING
Lancet. Vol. 1, Pg. 1479, 1973.

Ethynyl estradiol Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 233.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 6 , 1974,p. 77.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 21 , 1979,p. 233.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Ethynyl estradiol Safety Profile

Hazard Codes: T
Risk Statements: 45-22
45:May cause cancer 
22:Harmful if swallowed 
Safety Statements: 53-36/37/39-45
53:Avoid exposure - obtain special instruction before use 
36/37/39:Wear suitable protective clothing, gloves and eye/face protection 
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible 
WGK Germany: 3
RTECS: RC8925000
Confirmed carcinogen with experimental carcinogenic, tumorigenic, and neoplastigenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Human systemic effects by ingestion: glandular effects. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Ethynyl estradiol Specification

  Ethynyl estradiol (CAS NO.57-63-6), its Synonyms are (17-alpha)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17,diol ; 17-Ethinyl-3,17-estradiol ; 17-Ethinyl-3,17-oestradiol ; 17-Ethinylestradiol ; 17-Ethynyl-3,17-dihydroxy-1,3,5-oestratriene ; 17-Ethynylestradiol ; 17-Ethynyloestradiol ; 17-alpha-Ethinyl-17-beta-estradiol ; 17-alpha-Ethinyl-3,17-dihydroxy-delta(sup 1,3,5)-estratriene ; Aethinyloestradiolum ; Aethinyoestradiol ; 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 ; Primogyn C ; Primogyn M ; Progynon C ; Spanestrin .

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