Estradiol benzoate: Difference between revisions

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'''Estradiol benzoate''' ('''EB'''), a synthetic form of [[estrogen]], is an [[Estrogen ester|estrogen ester]] specifically, the 3-benzoate ester of [[estradiol]]. It is used in [[Hormone replacement therapy|HRT]] for menopausal symptoms and in [[Hormonal contraception|contraceptive]] pills. It is also employed in veterinary medicine as a component of hormonal veterinary products.
==Estradiol Benzoate==
 
[[File:Estradiol_benzoate.svg|Estradiol benzoate structure|thumb|right]]
 
'''Estradiol benzoate''' is a synthetic form of the naturally occurring hormone [[estradiol]], which is an [[estrogen]]. It is an [[estradiol ester]], specifically the 3-benzoate ester of estradiol, and is used in [[hormone replacement therapy]] and other medical applications.
 
==Pharmacology==
 
Estradiol benzoate is administered via [[intramuscular injection]]. Once in the body, it is slowly hydrolyzed into estradiol, the active form of the hormone. This process allows for a prolonged duration of action compared to estradiol itself. The pharmacokinetics of estradiol benzoate involve its absorption, distribution, metabolism, and excretion, which are influenced by the esterification of the estradiol molecule.
 
[[File:Estradiol_levels_after_single_intramuscular_injections_of_different_doses_of_estradiol_benzoate_in_premenopausal_women.png|Estradiol levels after single intramuscular injections of different doses of estradiol benzoate in premenopausal women|thumb|left]]


==Medical Uses==
==Medical Uses==
Estradiol benzoate is used primarily in [[Hormone replacement therapy|HRT]] for treating signs of menopause such as hot flashes and vaginal atrophy. It is also used in hormonal therapy for transgender women as part of the feminizing hormone therapy. In veterinary medicine, it is used to stimulate estrus in animals.


==Pharmacology==
Estradiol benzoate is used in various clinical settings, including:
===Pharmacodynamics===
 
Estradiol benzoate, like estradiol, binds to and activates the [[Estrogen receptor|estrogen receptor]]. Its estrogenic activity is responsible for the development and maintenance of female reproductive tissues and secondary sexual characteristics. It also has important effects on bone density, liver metabolism, and mental health.
* [[Hormone replacement therapy]] for [[menopausal symptoms]]
* Treatment of [[hypogonadism]] in women
* Part of [[feminizing hormone therapy]] for [[transgender women]]
 
[[File:Hormone_levels_with_twice-daily_injectable_estradiol_benzoate_in_transgender_women.png|Hormone levels with twice-daily injectable estradiol benzoate in transgender women|thumb|right]]
 
==Mechanism of Action==
 
As an estrogen, estradiol benzoate binds to and activates the [[estrogen receptor]], which then modulates the expression of various genes involved in the development and maintenance of female secondary sexual characteristics and reproductive tissues.
 
==Side Effects==
 
Common side effects of estradiol benzoate include:
 
* [[Nausea]]
* [[Breast tenderness]]
* [[Headache]]
* [[Fluid retention]]
 
Serious side effects can include an increased risk of [[thrombosis]] and [[breast cancer]].
 
==Pharmacokinetics==
 
The pharmacokinetics of estradiol benzoate are characterized by its slow release from the injection site and gradual conversion to estradiol. This results in a sustained elevation of estradiol levels in the blood.
 
[[File:Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png|Estradiol levels after a single 5 mg intramuscular injection of estradiol esters|thumb|left]]
 
==Comparative Pharmacokinetics==
 
Estradiol benzoate is one of several estradiol esters used in clinical practice. Others include [[estradiol valerate]] and [[estradiol cypionate]]. Each ester has different pharmacokinetic properties, influencing the duration and intensity of estradiol's effects.
 
[[File:Estradiol_levels_after_injections_of_estradiol,_estradiol_benzoate,_estradiol_valerate,_and_estradiol_undecylate_in_women.png|Estradiol levels after injections of estradiol, estradiol benzoate, estradiol valerate, and estradiol undecylate in women|thumb|right]]


===Pharmacokinetics===
==Vaginal Effects==
After administration, estradiol benzoate is slowly absorbed and hydrolyzed into estradiol, the active form, and benzoic acid. The conversion allows for a more prolonged duration of action compared to estradiol itself, making it suitable for less frequent dosing schedules in therapeutic applications.


==Adverse Effects==
Estradiol benzoate can induce [[vaginal cornification]], a process where the vaginal epithelium becomes keratinized, which is a marker of estrogenic activity.
The adverse effects of estradiol benzoate are similar to those of estradiol and other estrogens. These can include nausea, breast tenderness, headache, and an increased risk of thromboembolic events and certain types of cancers such as breast cancer. Monitoring and evaluation by a healthcare provider are essential to mitigate these risks.


==Chemistry==
[[File:Vaginal_cornification_with_a_single_intramuscular_injection_of_different_estradiol_esters_in_women.png|Vaginal cornification with a single intramuscular injection of different estradiol esters in women|thumb|left]]
Estradiol benzoate is a synthetic, steroidal estrogen and a derivative of estradiol. It is more lipophilic than estradiol due to the benzoate ester, which affects its pharmacokinetics, including absorption and half-life.


==History==
==Related Pages==
Estradiol benzoate was one of the first estrogen esters to be discovered and used medically. It has been available for medical use since the 1930s, making it one of the earliest forms of estrogen therapy available.


==Society and Culture==
* [[Estradiol]]
Legal status and availability of estradiol benzoate can vary by country. It remains an important component of hormone therapy regimens, despite the development of newer estrogen compounds and formulations.
* [[Estrogen]]
* [[Hormone replacement therapy]]
* [[Transgender hormone therapy]]


[[Category:Estrogens]]
[[Category:Estrogens]]
[[Category:Pharmacology]]
[[Category:Hormone replacement therapy]]
[[Category:Endocrinology]]
[[Category:Medicine]]
 
{{Pharmacology-stub}}
{{Endocrinology-stub}}
{{Medicine-stub}}
<gallery>
File:Estradiol.svg|Estradiol_benzoate
File:Hormone_levels_with_twice-daily_injectable_estradiol_benzoate_in_transgender_women.png|Hormone levels with twice-daily injectable estradiol benzoate in transgender women
File:Estradiol_levels_after_single_intramuscular_injections_of_different_doses_of_estradiol_benzoate_in_premenopausal_women.png|Estradiol levels after single intramuscular injections of different doses of estradiol benzoate in premenopausal women
File:Estradiol_levels_after_a_single_5_mg_intramuscular_injection_of_estradiol_esters.png|Estradiol levels after a single 5 mg intramuscular injection of estradiol esters
File:Estradiol_levels_after_injections_of_estradiol,_estradiol_benzoate,_estradiol_valerate,_and_estradiol_undecylate_in_women.png|Estradiol levels after injections of estradiol, estradiol benzoate, estradiol valerate, and estradiol undecylate in women
File:Idealized_curves_of_estradiol_levels_after_injection_of_different_estradiol_esters_in_women.png|Idealized curves of estradiol levels after injection of different estradiol esters in women
File:Vaginal_cornification_with_a_single_intramuscular_injection_of_different_estradiol_esters_in_women.png|Vaginal cornification with a single intramuscular injection of different estradiol esters in women
</gallery>
== Estradiol_benzoate ==
<gallery>
File:Estradiol_benzoate.svg|Estradiol benzoate
File:Trenbolone_acetate.svg|Trenbolone acetate
</gallery>

Latest revision as of 10:47, 23 March 2025

Estradiol Benzoate[edit]

Estradiol benzoate structure

Estradiol benzoate is a synthetic form of the naturally occurring hormone estradiol, which is an estrogen. It is an estradiol ester, specifically the 3-benzoate ester of estradiol, and is used in hormone replacement therapy and other medical applications.

Pharmacology[edit]

Estradiol benzoate is administered via intramuscular injection. Once in the body, it is slowly hydrolyzed into estradiol, the active form of the hormone. This process allows for a prolonged duration of action compared to estradiol itself. The pharmacokinetics of estradiol benzoate involve its absorption, distribution, metabolism, and excretion, which are influenced by the esterification of the estradiol molecule.

Estradiol levels after single intramuscular injections of different doses of estradiol benzoate in premenopausal women

Medical Uses[edit]

Estradiol benzoate is used in various clinical settings, including:

Hormone levels with twice-daily injectable estradiol benzoate in transgender women

Mechanism of Action[edit]

As an estrogen, estradiol benzoate binds to and activates the estrogen receptor, which then modulates the expression of various genes involved in the development and maintenance of female secondary sexual characteristics and reproductive tissues.

Side Effects[edit]

Common side effects of estradiol benzoate include:

Serious side effects can include an increased risk of thrombosis and breast cancer.

Pharmacokinetics[edit]

The pharmacokinetics of estradiol benzoate are characterized by its slow release from the injection site and gradual conversion to estradiol. This results in a sustained elevation of estradiol levels in the blood.

Estradiol levels after a single 5 mg intramuscular injection of estradiol esters

Comparative Pharmacokinetics[edit]

Estradiol benzoate is one of several estradiol esters used in clinical practice. Others include estradiol valerate and estradiol cypionate. Each ester has different pharmacokinetic properties, influencing the duration and intensity of estradiol's effects.

Estradiol levels after injections of estradiol, estradiol benzoate, estradiol valerate, and estradiol undecylate in women

Vaginal Effects[edit]

Estradiol benzoate can induce vaginal cornification, a process where the vaginal epithelium becomes keratinized, which is a marker of estrogenic activity.

Vaginal cornification with a single intramuscular injection of different estradiol esters in women

Related Pages[edit]