General Description
Fine white to creamy white powder. A synthetic steroid. Used in combination with progestogen as an oral contraceptive.
Reactivity Profile
ETHINYLESTRADIOL(57-63-6) may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to generate gaseous hydrogen.
Air & Water Reactions
Air and light sensitive . Insoluble in water.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits acrid smoke and fumes.
Potential Exposure
The working environment may be
contaminated during sex hormone manufacture, especially
during the extraction and purification of natural steroid hormones; grinding of raw materials; handling of powdered
products and recrystallization. Airborne particles of sex
hormones may be absorbed through the skin, ingested or
inhaled. Enteric absorption results in quick inactivation of
sex hormones in the liver. The rate of inactivation is
decreased for the oral, alkylated steroid hormones (methyl
testosterone, anabolic steroids, etc.). Sex hormones may
accumulate and reach relatively high levels even if their
absorption is intermittent. Consequently, repeated absorption of small amounts may be detrimental to health.
Intoxication by sex hormones may occur in almost all the
exposed workers if preventive measures are not taken. The
effect in the industrial sector is more successful than
the agricultural one (chemical caponizing of cockerels by
stilbestrol implants and incorporation of estrogens in feed
for body weight gain promotion in beef cattle), where measures taken are summary and the number of cases of intoxication is consequently bigger
Fire Hazard
The flash point data for this compound are not available. ETHINYLESTRADIOL is probably combustible.
First aid
Skin Contact: Flood all areas of body that
have contacted the substance with water. Don’t wait to
remove contaminated clothing; do it under the water stream.
Use soap to help assure removal. Isolate contaminated
clothing when removed to prevent contact by others. Eye
Contact: Remove any contact lenses at once. Immediately
flush eyes well with copious quantities of water or normal
saline for at least 2030 minutes. Seek medical attention.
Inhalation: Leave contaminated area immediately; breathe
fresh air. Proper respiratory protection must be supplied to
any rescuers. If coughing, difficult breathing or any other
symptoms develop, seek medical attention at once, even if
symptoms develop many hours after exposure. Ingestion:
Contact a physician, hospital or poison center at once. If the
victim is unconscious or convulsing, do not induce vomiting
or give anything by mouth. Assure that the patient’s airway
is open and lay him on his side with his head lower than his
body and transport immediately to a medical facility. If conscious and not convulsion, give a glass of water to dilute
the substance. Vomiting should not be induced without a
physician’s advice
Shipping
UN3249 Medicine, solid, toxic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials
Incompatibilities
May react exothermically with reducing
agents to generate flammable gaseous hydrogen.
Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine,
fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases, strong
acids, oxoacids, and epoxides.
Chemical Properties
Estradiol, 17-β-is an odorless white to yellow
crystalline substance.
Chemical Properties
Ethinylestradiol is a white to creamy-white
powder. Odorless.
Chemical Properties
Off-White to Light-Yellow Crystalline Powder
Waste Disposal
It is inappropriate and possibly dangerous to the environment to dispose of expired or
waste drugs and pharmaceuticals by flushing them down
the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed
with wet cat litter or coffee grounds, double-bagged in
plastic, discard in trash. Larger quantities shall carefully
take into consideration applicable DEA, EPA, and FDA
regulations. If possible return the pharmaceutical to the
manufacturer for proper disposal being careful to properly
label and securely package the material. Alternatively, the
waste pharmaceutical shall be labeled, securely packaged
and transported by a state licensed medical waste contractor
to dispose by burial in a licensed hazardous or toxic waste
landfill or incinerator
Originator
Estinyl,Schering,US,1944
Uses
A metabolite of 17a-Ethynylestradiol
Uses
A synthetic estradiol analog.
Uses
A synthetic steroid with high oral estrogenic potency
Uses
estrogen, plus progestogen as oral contraceptive
Definition
ChEBI: A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.
Manufacturing Process
In about 250 cc of liquid ammonia (cooled with dry ice and acetone) are
dissolved about 7.5 g of potassium and into the solution acetylene is passed
until the blue color has disappeared (about 3 hours). Then slowly a solution or
suspension of 3 g of estrone in 150 cc of benzene and 50 cc of ether is added.
The freezing mixture is removed, the whole allowed to stand for about 2
hours and the solution further stirred overnight. Thereupon the reaction
solution is treated with ice and water, acidified with sulfuric acid to an acid
reaction to Congo red and the solution extracted five times with ether. The
combined ether extracts are washed twice with water, once with 5% sodium
carbonate solution and again with water until the washing water is neutral.
Then the ether is evaporated, the residue dissolved in a little methanol and
diluted with water. The separated product is recrystallized from aqueous
methanol. The yield amounts to 2.77 g. The 17-ethinyl-estradiol-3,17 thus obtained melts at 142°C to 144°C.
Brand name
Estinyl (Schering); Feminone
(Pharmacia & Upjohn); Lynoral (Organon).
Therapeutic Function
Estrogen
Biochem/physiol Actions
17α-Ethynylestradiol is an orally bio-active synthetic estrogen used as an oral contraceptive.
Synthesis
Ethinyl estradiol, 17|á-ethinyl-1,3,5(10)-estratrien-3-17|?-diol (28.1.26),
is made either by condensing estrone with acetylene in the presence of potassium hydroxide
(Favorskii reaction), or by reacting sodium acetylenide in liquid ammonia with estrone.
Purification Methods
17--Ethynylestradiol forms a hemihydrate on recrystallising from MeOH/H2O. It dehydrates on melting and remelts on further heating at m 182-184o. The UV has max at 281nm ( 2040) in EtOH. Its solubility is 17% in EtOH, 25% in Et2O, 20% in Me2CO, 25% in dioxane and 5% in CHCl3. [Petit & Muller Bull Soc Chim Fr 121 1951.] The diacetyl derivative has m 143-144o (from MeOH) and [] D 20 +1o (c 1, CHCl3) [Mills et al. J Am Chem Soc 80 6118 1958]. [Beilstein 6 IV 6877.]
