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HomeProduct name listEstradiol benzoate

Estradiol benzoate

Synonym(s):β-Estradiol 3-benzoate;1,3,5(10)-Estratriene-3,17β-diol 3-benzoate;3,17β-Dihydroxy-1,3,5(10)-estratriene 3-benzoate;3-Benzoyloxy-17β-estrol

  • CAS NO.:50-50-0
  • Empirical Formula: C25H28O3
  • Molecular Weight: 376.5
  • MDL number: MFCD00003692
  • EINECS: 200-043-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
Estradiol benzoate Structural

What is Estradiol benzoate?

Chemical properties

White solid

The Uses of Estradiol benzoate

Estradiol is the major estrogen secreted by the premenopausal ovary. Estradiol benzoate is an estradiol analog which contains a benzyl ester at the C-3 position. Estradiol benzoate is useful in the tr eatment of lesions produced by diminution of bodily production of estrogens.

The Uses of Estradiol benzoate

antiacne, antineoplastic

The Uses of Estradiol benzoate

Estradiol is the major estrogen secreted by the premenopausal ovary. Estradiol benzoate is an estradiol analog which contains a benzyl ester at the C-3 position. Estradiol benzoate is useful in the treatment of lesions produced by diminution of bodily production of estrogens.

Indications

Estradiol benzoate is not currently available in any FDA or Health Canada approved products.

Background

Estradiol Benzoate is a pro-drug ester of Estradiol, a naturally occurring hormone that circulates endogenously within the human body. Estradiol is the most potent form of all mammalian estrogenic steroids and acts as the major female sex hormone. As a pro-drug of estradiol, estradiol benzoate therefore has the same downstream effects within the body through binding to the Estrogen Receptor (ER) including ERα and ERβ subtypes, which are located in various tissues including in the breasts, uterus, ovaries, skin, prostate, bone, fat, and brain.
Estradiol is commonly produced with an ester side-chain as endogenous estradiol has very low oral bioavailability on its own (2-10%). First-pass metabolism by the gut and the liver quickly degrades the estradiol molecule before it gets a chance to enter systemic circulation and exert its estrogenic effects . Esterification of estradiol aims to improves absorption and bioavailability after oral administration (such as with Estradiol valerate) or to sustain release from depot intramuscular injections (such as with Estradiol Cypionate) through improved lipophilicity. Following absorption, the esters are cleaved, resulting in the release of endogenous estradiol, or 17β-estradiol. Ester pro-drugs of estradiol are therefore considered to be bioidentical forms of estrogen .
Estradiol benzoate is not currently available in Canada or the US.

What are the applications of Application

Estradiol Benzoate is a steroid used for biological research purposes

Definition

ChEBI: A benzoate ester resulting from the formal condensation of benzoic acid with the phenolic hydroxy group of 17beta-estradiol.

Pharmacokinetics

Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone and estriol, at the cellular level.

Clinical Use

Estradiol is a semisynthetic estrogen compound. Its effects will mimic that of estrogen in animals. The most common use in small animals has been to terminate pregnancy.
Estradiol benzoate also has been used to terminate pregnancy (5-10 mg/kg divided into two or three SQ injections). Estradiol cypionate formulation had high efficacy (95%), but it had serious adverse effects and is not recommended. Estradiol cypionate is longer acting and more potent than other estrogen formulations. Estradiol valerate injection (20 mg/mL) is also available for human medicine to treat hypoestrogenism.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Human reproductive effects by intramuscular route: menstrual cycle changes and disorders. Experimental reproductive effects. Mutation data reported. A steroid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ESTRADIOL.

Metabolism

Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450.

Properties of Estradiol benzoate

Melting point: 191-198 °C(lit.)
Boiling point: 465.03°C (rough estimate)
alpha  D25 +58 to +63° (c = 2 in dioxane)
Density  1.0493 (rough estimate)
refractive index  1.5460 (estimate)
storage temp.  2-8°C
solubility  Practically insoluble in water, freely soluble in methylene chloride, sparingly soluble in acetone, slightly soluble in methanol.
form  neat
pka 15.06±0.40(Predicted)
form  Solid
color  White
Water Solubility  0.4mg/L(25 ºC)
Merck  3703
BRN  3107526
CAS DataBase Reference 50-50-0(CAS DataBase Reference)
NIST Chemistry Reference Estradiol benzoate(50-50-0)

Safety information for Estradiol benzoate

Signal word Danger
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H351:Carcinogenicity
Precautionary Statement Codes 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.
P308+P313:IF exposed or concerned: Get medical advice/attention.
P405:Store locked up.
P501:Dispose of contents/container to..…

Computed Descriptors for Estradiol benzoate

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