Estradiol valerate

Estradiol valerate Basic information
Product Name:Estradiol valerate
Synonyms:delestrogen;delestrogen4x;dura-estradiol;estradiol17-beta-valerate;estradiolvalerianate;estraval;17BETA-ESTRADIOL VALERATE;17B-ESTRADIOL-17-VALERATE
CAS:979-32-8
MF:C23H32O3
MW:356.51
EINECS:213-559-2
Product Categories:Hormone Drugs;progestogen estrogen;Steroids;Intermediates & Fine Chemicals;Pharmaceuticals;DELESTRGEN;API;979-32-8
Mol File:979-32-8.mol
Estradiol valerate Structure
Estradiol valerate Chemical Properties
Melting point 144°C
Boiling point 438.83°C (rough estimate)
density 1.1024 (rough estimate)
refractive index 1.4700 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Practically insoluble in water, soluble in alcohol.
pka10.25±0.60(Predicted)
form neat
Merck 13,3738
BRN 2480357
InChIInChI=1/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/s3
InChIKeyRSEPBGGWRJCQGY-RBRWEJTLSA-N
SMILESC[C@]12CC[C@]3([H])C4C=CC(O)=CC=4CC[C@@]3([H])[C@]1([H])CC[C@@H]2OC(=O)CCCC |&1:1,4,15,17,21,r|
CAS DataBase Reference979-32-8(CAS DataBase Reference)
Safety Information
Hazard Codes T
Risk Statements 60-61
Safety Statements 53-45
WGK Germany 3
RTECS KG5793000
HS Code 29372390
MSDS Information
ProviderLanguage
SigmaAldrich English
Estradiol valerate Usage And Synthesis
DescriptionEstradiol valerate (EV), sold for use by mouth under the brand name Progynova and for use by injection under the brand names Delestrogen and Progynon Depot among others, is an estrogen medication. In women, it is used in hormone therapy for menopausal symptoms and low estrogen levels, hormone therapy for transgender women, and in hormonal birth control. It is also used in the treatment of prostate cancer in men. The medication is taken by mouth or by injection into muscle or fat once every 1 to 4 weeks.
Chemical PropertiesWhite to off-white crystalline powder, odorless. Insoluble in water, easily soluble in ethanol, acetone, chloroform, slightly soluble in vegetable oil.
OriginatorDelestrogen,Squibb,US,1954
UsesEstradiol valerate is a female hormone (estrogen). It is used to reduce symptoms of menopause which are vaginal dryness, hot flashes, and others. The symptoms of menopause manifest because the body is making less estrogen; with estradiol valerate, these symptoms are brought to the lowest minimum. This medication therapy can also produce enough estrogen in women with ovarian failure, hypogonadism and can be used by men to treat prostate cancer (palliation only).
IndicationsEstradiol valerate is commercially available as an intramuscular injection as the product Delestrogen and is indicated for the treatment of moderate to severe vasomotor symptoms and vulvovaginal atrophy due to menopause, for the treatment of hypoestrogenism due to hypogonadism, castration or primary ovarian failure, and for the treatment of advanced androgen-dependent carcinoma of the prostate (for palliation only). Estradiol valerate is also available in combination with Dienogest as the commercially available product Natazia used for the prevention of pregnancy and for the treatment of heavy menstrual bleeding.
DefinitionChEBI: Estradiol valerate is a steroid ester. It is the parenterally-administered synthetic valerate ester of estradiol, a steroid sex hormone vital to the maintenance of fertility and secondary sexual characteristics in females.
Manufacturing Process2.3 parts of estradiol are mixed with 12 parts of pyridine and 10 parts of nvaleric anhydride and the mixture is heated for some time at 115°C in the oil bath. The cooled solution is mixed with 250 parts of water, whereupon an oil separates; this is extracted with ether. The separated ethereal solution is washed successively with N sulfuric acid, water, N sodium carbonate solution and water and then dried. The ether is then removed and the residue purified by distillation in a high vacuum. The estradiol di-n-valerate forms a yellowish oil according to US Patent 2,205,627.
1 part of estradiol-3,17-n-divalerianate (boiling point at 0.01 mm = 220° to 230°C bath temperature; made, e.g., by the action of n-valeric anhydride on a solution of estradiol in pyridine) is mixed with 50 parts of a solution of 0.5% strength of potassium carbonate in methyl alcohol of 95% strength, and the whole is stirred for some time at 20°C. The oily n-di-valerianate passes gradually into solution. The solution is neutralized and the precipitate is produced by the addition of about 200 parts of water. This finely crystalline product is filtered and washed successively with water, dilute sodium carbonate solution and again with water. It may be further purified by crystallization from a mixture of methyl alcohol and water. The estradiol-17- mono-n-valerianate melts at 144° to 145°C according to US Patent 2,233,025.
Brand nameDelestrogen (King).
Therapeutic FunctionEstrogen
General DescriptionEstradiol valerate is a synthetic hormone that is extensively metabolized to estradiol and valeric acid before reaching the systemic circulation. It is well suited for treatment of the characteristic symptoms accompanying menopause in women.
Side effectsAs with all pharmaceutical medicines, some unwanted effects can occur from the use of estradiol valerate tablets.
Always consult a physician for medical advice before use.
Common side effects may include: bloating, vomiting, nausea, breast tenderness, headache, weight changes, and mood changes.
More severe side effects may include mental changes, breast lumps, vaginal bleeding, liver damage, increased thirst, and sudden vision loss.
Safety ProfileSuspected carcinogen with carcinogenic and teratogenic data. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTRADIOL.
Estradiol valerate Preparation Products And Raw materials
Raw materialsVALERIC ANHYDRIDE-->Potassium carbonate-->β-Estradiol
Estradiol valerate MAGNESIUM DIPROPYLACETATE HYDRATE Estradiol undecylate Estradiol 17-Octadecanoate-1-14C Ethynyl estradiol Oestradiol 17-heptanoate CycloProvera 3,17BETA-ESTRADIOL-3-METHYL ETHER-17-DECANOATE 1,3,5(10)-ESTRATRIEN-3,17-BETA-DIOL 3-ACETATE, 17-STEARATE ESTRADIOL 17-O-OCTADECANOATE Pivalic acid 1,3,5(10)-ESTRATRIEN-3,17-BETA-DIOL DICYCLOPENTYLPROPIONATE 1,3,5(10)-ESTRATRIEN-3,17-BETA-DIOL DISTEARATE Estradiol 1,3,5(10)-ESTRATRIEN-3,17-BETA-DIOL 3-BENZOATE, 17-VALERATE Estradiol benzoate Estradiol Cypionate HT-2 TOXIN

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