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| | Estradiol valerate Basic information |
| | 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. | | pka | 10.25±0.60(Predicted) | | form | neat | | Merck | 13,3738 | | BRN | 2480357 | | InChI | InChI=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 | | InChIKey | RSEPBGGWRJCQGY-RBRWEJTLSA-N | | SMILES | C[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 Reference | 979-32-8(CAS DataBase Reference) |
| Hazard Codes | T | | Risk Statements | 60-61 | | Safety Statements | 53-45 | | WGK Germany | 3 | | RTECS | KG5793000 | | HS Code | 29372390 |
| | Estradiol valerate Usage And Synthesis |
| Description | Estradiol 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 Properties | White to off-white crystalline powder, odorless. Insoluble in water, easily soluble in ethanol, acetone, chloroform, slightly soluble in vegetable oil. | | Originator | Delestrogen,Squibb,US,1954 | | Uses | Estradiol 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). | | Indications | Estradiol 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. | | Definition | ChEBI: 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 Process | 2.3 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 name | Delestrogen (King). | | Therapeutic Function | Estrogen | | General Description | Estradiol 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 effects | As 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 Profile | Suspected 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 |
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