3D Mol Similar

Ethynyl estradiol

: 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; CAS No.: 57-63-6; Molecular Weight：296.40336; Modify Date.: 2023-02-18 05:23; Introduction: Ethynyl estradiol (EE) is a synthetic form of estrogen that is majorly employed in numerous hormonal contraceptives in combination with progestins. Occasionally, it is also used as a constituent of menopausal hormone therapy with combination with progestins for treating menopausal symptoms. Previously, the drug was used solely for numerous indications such as treatment of prostate cancer and gynecological disorders.Ethynyl estradiol is a semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It is normally administred orally and is marketed mostly as a combination oral contraceptive under various brand names such as Alesse, Tri-cyclen, Yasmin, and Triphasil. A black box warning is normally labelled on the packaging that states that the drug should not be used in smoking women who are over 35 years old as it can lead to increased risk of serious cardiovascular side effects. View more+

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1. Names and Identifiers

: 1.1 Name; Ethynyl estradiol; 1.2 Synonyms; (17b)-17-ethynylestra-1(10),2,4-triene-3,17-diol (17α)-19-Norpregna-1(10),2,4-trien-20-yne-3,17-diol (17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol (8R,9S,13S,14S,17R)-17-éthynyl-13-méthyl-7,8,9,11,12,13,14,15,16,17-décahydro-6H-cyclopenta[a]phénanthrène-3,17-diol (8R,9S,13S,14S,17R)-17-Ethinyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3,17-diol (8α,13α,17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol 1,3,5(10)-ESTRATRIEN-17-ALPHA-ETHYNYL-3,17-BETA-DIOL 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 17-alpha-ethynyl-17-beta-oestradiol 17alpha-Ethynyl-17beta-oestradiol 17ALPHA-ETHYNYL-DELTA1,3,5(10)-ESTRA-TRIENE-3,17BETA-DIOL 17-alpha-ethynylestra-1,3,5(10)-triene-3,17-beta-diol 17alpha-Ethynylestra-1,3,5(10)-triene-3,17beta-diol 17alpha-ethynylestradiol 17-Ethynyl-3-17-dihydroxy-1,3,5-oestratriene 17-ethynyl-estradio 17-Ethynyloestra-1,3,5(10)- 17-Ethynyloestra-1,3,5(10)-triene-3,17Β-diol 17-ethynyloestradiol 17α-Ethynyl-1,3,5(10)-estratriene-3,17Β-diol 17α-ethynylestradiol 19-NOR-1,3,5[10],17ALPHA-PREGNATRIEN-20-YNE-3,17-DIOL 19-NORPREGNA-1,3,5(10)-TRIEN-20-YNE-3,17ALPHA-DIOL ACETENYL ESTRADIOL Anovlar diprol Dufaston eed EINECS 200-342-2 Ertonyl Esteed Estigyn Estinyl Estoral estra-1(10),2,4-triene-3,17-diol, 17-ethynyl-, (17b)- Estra-1,3,5(10)-triene-3,17-diol, 17-ethynyl-, (17Β)- Estra-1,3,5(10)-triene-3,17-diol, 17-ethynyl-, (8α,13α,17β)- Estra-1,3,5(10)-triene-3,17Β-diol, 17-ethynyl- Estra-1,3,5(10)-triene-3,17Β-diol, 17α-ethynyl- Estra-1,3,5[10]-triene-3,17Β-diol, 17-ethynyl- Ethinyl Estradial ETHINYL ESTRADIOL Ethinyl estradiol (USP) Ethinyloestradiol ETHYNYLESTRADIOL Etinilestradiol Etivex Gynolett Kolpolyn LYNORAL MFCD00003690 Progylut Progynon M Prosexol Ylestrol; View all

1.3 CAS No.: 57-63-6

1.4 CID: 5991

1.5 EINECS(EC#): 200-342-2

1.6 Molecular Formula: C20H24O2 (isomer)

1.7 Inchi: 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

1.8 InChIkey: BFPYWIDHMRZLRN-SLHNCBLASA-N

1.9 Canonical Smiles: CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O

1.10 Isomers Smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O

2. Properties

2.1 Density: 1.21

2.1 Melting point: 182-183℃

2.1 Boiling point: 457.2°C at 760mmHg

2.1 Refractive index: -30 ° (C=0.4, Pyridine)

2.1 Flash Point: 211.2°C

2.1 Precise Quality: 296.17800

2.1 PSA: 40.46000

2.1 logP: 3.61260

2.1 Solubility: ethanol: 50?mg/mL, clear, slightly yellow

2.2 Appearance: Off-White to Light-Yellow Crystalline Powder

2.3 Chemical Properties: Off-White to Light-Yellow Crystalline Powder

2.4 Color/Form: Hemihydrate, fine needles from methanol and water

2.5 Decomposition: When heated to decomposition it emits acrid smoke and irritating fumes.

2.6 Odor: Odorless

2.7 pKa: pKa 10.32 (Uncertain)

2.8 Water Solubility: ethanol: 50?mg/mL, clear, slightly yellow

2.9 Spectral Properties: Optical rotation at 24 deg C for sodium line: 3.5 deg +/- 0.5 deg (c = 2 in dioxane); -29.5 deg +/- 1 deg (c = 2 in pyridine). UV max (ethanol): 281 nm (molar extinction coefficient; dielectric constant = 2040 +/- 60 g-moles/l)

2.10 StorageTemp: room temp

3. Use and Manufacturing

3.1 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.

3.2 History: Ethynyl estradiol was first developed in 1930 and officially introduced for medical used in 1943. In the 1960s, the drug was widely used in birth control pills. EE is currently found in most combined forms of birth control pills, which makes it one of the most used estrogens.

3.3 Potential Exposure: The working environment may becontaminated during sex hormone manufacture, especiallyduring the extraction and purification of natural steroid hormones; grinding of raw materials; handling of powderedproducts and recrystallization. Airborne particles of sexhormones may be absorbed through the skin, ingested orinhaled. Enteric absorption results in quick inactivation ofsex hormones in the liver. The rate of inactivation isdecreased for the oral, alkylated steroid hormones (methyltestosterone, anabolic steroids, etc.). Sex hormones mayaccumulate and reach relatively high levels even if theirabsorption is intermittent. Consequently, repeated absorption of small amounts may be detrimental to health.Intoxication by sex hormones may occur in almost all theexposed workers if preventive measures are not taken. Theeffect in the industrial sector is more successful thanthe agricultural one (chemical caponizing of cockerels bystilbestrol implants and incorporation of estrogens in feedfor body weight gain promotion in beef cattle), where measures taken are summary and the number of cases of intoxication is consequently bigger; View all

3.4 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.]

3.5 Shipping: UN3249 Medicine, solid, toxic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials

3.6 Usage: Ethnynyl estradiol is majorly used to control pregnancy after sex as a contraception in combined oral contraceptives (COC), which are also referred to as birth control. EE is not only used in preventing pregnancy but is also employed in the treatment of absence of menstruation, acne, as well as symptoms during menstruation. It majorly works by preventing ovulation (the release of an egg) during the menstrual cycle. Further, it acts by making the vaginal fluid thicker to help in preventing sperm from fertilizing the released egg. It also changes the lining of the uterus to prevent attachment of a fertilized egg. EE also works by making the menstruation cycle more regular, decreasing blood loss and painful periods, and decreasing the risk of ovarian cysts.EE is also used as menopausal hormone therapy (HRT) which has numerous benefits such as vaginal itching, vaginal dryness (which normally causes pain during sexual intercourse), and depressed mood. Previously, it was used as a constituent of feminizing hormone therapy for transgender women; however, the use of estradiol has largely superseded it in this therapy. The drug can also be used in preventing osteoporosis and in treating hypogonadism in women and has been used as palliative care for breast cancer in women and prostate cancer in men.; View all

3.7 Waste Disposal: It is inappropriate and possibly dangerous to the environment to dispose of expired orwaste drugs and pharmaceuticals by flushing them downthe toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixedwith wet cat litter or coffee grounds, double-bagged inplastic, discard in trash. Larger quantities shall carefullytake into consideration applicable DEA, EPA, and FDAregulations. If possible return the pharmaceutical to themanufacturer for proper disposal being careful to properlylabel and securely package the material. Alternatively, thewaste pharmaceutical shall be labeled, securely packagedand transported by a state licensed medical waste contractorto dispose by burial in a licensed hazardous or toxic wastelandfill or incinerator Ethynyl estradiol Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Symbol: GHS07;GHS08;

4.1 Hazard Codes: T

4.1 Signal Word: DANGER

4.1 Risk Statements: R45;R22

4.1 Safety Statements: S53;S36/37/39;S45

4.1 Exposure Standards and Regulations: Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

4.2 Octanol/Water Partition Coefficient: log Kow = 3.67

4.3 Fire Hazard: The flash point data for Ethynyl estradiol are not available. Ethynyl estradiol is probably combustible.

4.4 Other Preventative Measures: Workrooms must be kept very clean, & contaminated clothing should be destroyed or cleaned. Complete prevention of environmental pollution is nevertheless not easy, because of persistence of light powder in air. worker must therefore co-operate in prevention of chronic intoxication.

4.5 Hazard Declaration: H302; H350

4.5 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.6 RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution

4.6 Safety Profile: 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. See also ESTRADIOL

4.7 Caution Statement: P201-P308 + P313

4.7 Incompatibilities: May react exothermically with reducingagents 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, strongacids, oxoacids, and epoxides.

4.8 WGK Germany: 3

4.8 RTECS: RC8925000

4.8 Report: 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.; View all

4.9 Safety: Hazard Codes: T
Risk Statements: 45-22
R45:May cause cancer
R22:Harmful if swallowed
Safety Statements: 53-36/37/39-45
S53:Avoid exposure - obtain special instruction before use
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45: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.

4.10 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.

4.11 Toxicity

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.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Carcinogenicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H350 May cause cancer
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

57-63-6Total: 8 Synthesis Route

68-22-4 286 Suppliers

57-63-6 339 Suppliers

Literatures:
Rao, Pemmaraju N.; Cessac, James W.; Kim, Hyun K. Steroids, 1994 , vol. 59, # 11 p. 621 - 627
Yield: ~78%

72-33-3 91 Suppliers

57-63-6 339 Suppliers

26011-40-5 2 Suppliers

22415-44-7

Literatures:
Steroids, , vol. 36, # 3 p. 255 - 282
Yield: null

72-33-3 91 Suppliers

57-63-6 339 Suppliers

26011-40-5 2 Suppliers

22415-44-7

60134-76-1

75803-39-3 1 Suppliers

75812-41-8

Literatures:
Steroids, , vol. 36, # 3 p. 255 - 282
Yield: null

View all

8. Precursor and Product

precursor:

72-33-3

68-22-4

74-86-2

1111-63-3

4301-14-8

53-16-7

28913-23-7

product :

75803-37-1

60134-76-1

50394-90-6

72-33-3

75803-39-3

5779-47-5

75803-36-0

75812-41-8

13258-68-9

242130-33-2

24560-70-1

50394-89-3

50-28-2

7678-95-7

View all

9. Other Information

9.0 Merck: 14,3734

9.1 BRN: 2419975

9.2 Target: Value

9.3 Description: Ethynyl estradiol (EE) is a synthetic form of estrogen that is majorly employed in numerous hormonal contraceptives in combination with progestins. Occasionally, it is also used as a constituent of menopausal hormone therapy with combination with progestins for treating menopausal symptoms. Previously, the drug was used solely for numerous indications such as treatment of prostate cancer and gynecological disorders.
Ethynyl estradiol is a semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It is normally administred orally and is marketed mostly as a combination oral contraceptive under various brand names such as Alesse, Tri-cyclen, Yasmin, and Triphasil. A black box warning is normally labelled on the packaging that states that the drug should not be used in smoking women who are over 35 years old as it can lead to increased risk of serious cardiovascular side effects.

9.4 History: Ethynyl estradiol was first developed in 1930 and officially introduced for medical used in 1943. In the 1960s, the drug was widely used in birth control pills. EE is currently found in most combined forms of birth control pills, which makes it one of the most used estrogens.

9.5 Indications: Ethynyl estradiol is used for treatment of moderate to severe vasomotor symptoms such as night sweats, hot flashes, and flushing that are associated with the menopause, prostatic carcinoma-palliative therapy of advanced disease, female hypogonadism, as emergency contraceptive, breast cancer, and as an oral contraceptive.

9.6 Pharmacodynamics: Ethynyl estradiol is a synthetic derivative of the natural estrogen estradiol. The drug is one of two widely used in oral contraceptive pills. Mestranol is the other drug that is normally converted to ethinyl estradiol before it becomes biologically active. EE is used together with norethindrone as an oral contraceptive agent.

9.7 Mechanism of Action: The estrogen in the drug diffuse into their target cells before interacting with a protein receptor. Notably, target cells include the female reproductive tract, the hypothalamus, the mammary gland, and the pituitary. Estrogens act by increasing the hepatic synthesis of thyroid binding globulin (TBG), sex hormone binding globulin (SHBG) as well as other serum proteins. It also acts by suppressing follicle-stimulating hormone (FSH) from anterior pituitary. All these activities are initiated by fist binding to the estrogen receptors. The hypothalamic-pituitary system is suppressed by the combination of an estrogen with a progestin, which decreases the secretion of gonadorotropin-releasing hormone (GnRH).

9.8 Medical Uses: Ethnynyl estradiol is majorly used to control pregnancy after sex as a contraception in combined oral contraceptives (COC), which are also referred to as birth control. EE is not only used in preventing pregnancy but is also employed in the treatment of absence of menstruation, acne, as well as symptoms during menstruation. It majorly works by preventing ovulation (the release of an egg) during the menstrual cycle. Further, it acts by making the vaginal fluid thicker to help in preventing sperm from fertilizing the released egg. It also changes the lining of the uterus to prevent attachment of a fertilized egg. EE also works by making the menstruation cycle more regular, decreasing blood loss and painful periods, and decreasing the risk of ovarian cysts.
EE is also used as menopausal hormone therapy (HRT) which has numerous benefits such as vaginal itching, vaginal dryness (which normally causes pain during sexual intercourse), and depressed mood. Previously, it was used as a constituent of feminizing hormone therapy for transgender women; however, the use of estradiol has largely superseded it in this therapy. The drug can also be used in preventing osteoporosis and in treating hypogonadism in women and has been used as palliative care for breast cancer in women and prostate cancer in men.; View all

9.9 Contraindications: Ethnynyl estradiol should not be prescribed to individuals with history of susceptibility to venous or arterial thrombosis (blood clots) as it can lead to increased cardiovascular problems such as myocardial infarction, venous thromboembolism, and ischemic stroke. As such, it women with acute deep vein thrombosis or pulmonary embolism, any vascular disease history of DVT/PE, and complicated valvular heart disease are not advised to take the drug.

9.10 Side Effects: The side effects of EE include vomiting, nausea, headache, tenderness of the breast, abdominal cramps/bloating, swelling of the feet/ankles, and change in weight. In case of severe effects, one should immediately contact the doctor. EE can also cause irregular periods, which is considered normal.

9.11 Precautions: Before taking EE, it is important to inform the doctor or pharmacist if you allergic to the drug or to any other estrogens such as mestranol. It is also important to inform the doctor if one has a medical history of blood clots, for instance in the eyes, legs, and lungs. The medication can also affect blood sugar levels if one is diabetic. However, it is important to monitor the blood sugar levels and share it with the doctor in case one is using the drug.

9.12 Interactions: Drug interactions may change how EE works or might increase its side effects. Products that can interact with the drug include aromatase inhibitors (such as exemestane and anastrozole), tizanidine, tamoxifen, and tranexamic. It can also interact with certain combination products that are normally used to treat chronic hepatitis C. some drugs interact with EE by decreasing the amount of the drug in the body.

9.13 Description: Estrogens direct the development of the female genotype in embryogenesis and at puberty. Estradiol is the major estrogen secreted by the premenopausal ovary. Ethynyl estradiol is a synthetic analog of 17β-estradiol (Item No. 10006315). A USP-approved grade of ethynyl estradiol is often formulated in combination with a progestin such as norgestrel (Item No. 10006319)/levonorgestrel (Item No. 10006318) or desogestrel and provided for use as an oral contraceptive. Efficacy of oral administration of ethynyl estradiol is facilitated by the ethynyl substitution at the C-17 position, which inhibits first pass hepatic metabolism. Ethynyl estradiol is also rapidly and almost completely absorbed from the gastrointestinal tract.

9.14 Chemical Properties: Off-White to Light-Yellow Crystalline Powder

9.15 Chemical Properties: Ethinylestradiol is a white to creamy-white powder. Odorless.

9.16 Chemical Properties: Estradiol, 17-β-is an odorless white to yellow crystalline substance.

9.17 Originator: Estinyl,Schering,US,1944

9.18 Uses: A synthetic estradiol analog.

9.19 Uses: A metabolite of 17a-Ethynylestradiol

9.20 Uses: A synthetic steroid with high oral estrogenic potency

9.21 Uses: estrogen, plus progestogen as oral contraceptive

9.22 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.

9.23 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.; View all

9.24 Brand name: Estinyl (Schering); Feminone (Pharmacia & Upjohn); Lynoral (Organon).

9.25 Therapeutic Function: Estrogen

9.26 General Description: 17 -Ethinyl estradiol has thegreatest advantage over other estradiol products of beingorally active. It is equal to estradiol in potency by injectionbut is 15 to 20 times more orally active. The primary metabolicpath for ethinyl estradiol is 2-hydroxylation bycytochrome P450 isozyme 3A4 (CYP3A4), followed byconversion to the 2- and 3-methyl ethers by catechol-Omethyltransferase.The 3-methyl ether of ethinyl estradiolis mestranol, USP, used in oral contraceptives. Mestranolis a prodrug that is 3-O-demethylated to the active ethinylestradiol. An oral dose of about 50 μg of mestranol has anestrogenic action approximately equivalent to 35 g oforal ethinyl estradiol. The demethylation is mainly mediatedby CYP2C9.

9.27 General Description: Fine white to creamy white powder. A synthetic steroid. Used in combination with progestogen as an oral contraceptive.

9.28 Air & Water Reactions: Air and light sensitive . Insoluble in water.

9.29 Reactivity Profile: Ethynyl estradiol may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to generate gaseous hydrogen.

9.30 Health Hazard: ACUTE/CHRONIC HAZARDS: When heated to decomposition Ethynyl estradiol emits acrid smoke and fumes.

9.31 Fire Hazard: The flash point data for Ethynyl estradiol are not available. Ethynyl estradiol is probably combustible.

9.32 Biochem/physiol Actions: 17α-Ethynylestradiol is an orally bio-active synthetic estrogen used as an oral contraceptive.

9.33 Mechanism of action: Synthetic estrogen with potent activity (inhibition of ovulation), widely used in oral contraceptives. Manufactured from natural estrogen, estrone, by reaction with potassium acetylide (HCRCK) in liquid ammonia. The synthetic 17α-ethynyl derivative of estradiol-17β. The 17α-ethynyl group increases the in vivo potency of estradiol- 17β by blocking the action of 17β-dehydrogenase, a major pathway of estradiol-17β metabolic inactivation. It is thus active orally and is among the most potent of the known estrogenic compounds.

9.34 Safety Profile: 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. See also ESTRADIOL

9.35 Chemical Synthesis: Ethinyl estradiol, 17α-ethinyl-1,3,5(10)-estratrien-3-17β-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.

9.36 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; View all

9.37 Shipping: UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials

9.38 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.]

9.39 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.

9.40 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

9.41 Description: Estrogens direct the development of the female genotype in embryogenesis and at puberty. Estradiol is the major estrogen secreted by the premenopausal ovary. Ethynyl estradiol is a synthetic analog of 17β-estradiol . A USP-approved grade of ethynyl estradiol is often formulated in combination with a progestin such as norgestrel /levonorgestrel or desogestrel and provided for use as an oral contraceptive. Efficacy of oral administration of ethynyl estradiol is facilitated by the ethynyl substitution at the C-17 position, which inhibits first pass hepatic metabolism. Ethynyl estradiol is also rapidly and almost completely absorbed from the gastrointestinal tract.

10. Computational chemical data

Molecular Weight: 296.40336g/mol
Molecular Formula: C₂₀H₂₄O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 296.177630004
Monoisotopic Mass: 296.177630004
Complexity: 505
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 40.5
Heavy Atom Count: 22
Defined Atom Stereocenter Count: 5
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDBAAAAGgAACAAAD0SAmAAyBoAAAgDAGiBCAAgCAAAgIAAIiAAGCIgIJiKCERKAcAAkwBEImAeAwPAPoAABAAAQAADAAAYAACAAAYAADAAAAA==

11. Question & Answer

Can you choose unqualified manufacturers to buy Ethynyl estradiol? Apr 12 2023
Ethynyl estradiol is an organic compound, mainly white or off-white in color, in crystalline powder form, soluble in cyclohexane and propanol. Ethynyl estradiol plays a crucial role in the pharmaceuti..
What are the indications for Ethynyl estradiol? Jan 26 2023
1. Ethynyl estradiol is used to supplement insufficient estrogen levels and treat female gonadal dysfunction, amenorrhea, and menopausal syndrome. 2. It is used for the treatment of advanced breast ca..
How to effectively promote and sell Ethynyl estradiol? Nov 11 2021
For pharmaceutical processing companies, the biggest challenge after producing drugs is how to market and sell them. With a wide variety of similar drugs available, it is important to pay attention to..
What are the main indications of Ethynyl estradiol? Sep 15 2021
The relationship between chemical products and people's lives is inseparable. More and more consumers rely on chemical products to ensure their health. Some consumers can improve their physical illnes..

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