Epitiostanol: Difference between revisions

Latest revision as of 04:05, 13 February 2025

Overview[edit]

Epitiostanol is a synthetic anabolic-androgenic steroid (AAS) that was developed in the 1960s. It is primarily known for its use in the treatment of breast cancer. Epitiostanol is a derivative of dihydrotestosterone (DHT) and is characterized by its unique chemical structure, which includes a sulfur atom.

Chemical Structure[edit]

Epitiostanol is chemically known as 2_,3_-epithio-5_-androstan-17_-ol. The presence of the epithio group (a sulfur atom replacing an oxygen atom) in its structure is a distinguishing feature that contributes to its biological activity.

Mechanism of Action[edit]

Epitiostanol functions as an anti-estrogenic agent. It binds to estrogen receptors in breast tissue, thereby inhibiting the growth of estrogen-dependent tumors. Unlike other anti-estrogens, epitiostanol does not exhibit estrogenic activity, making it a pure anti-estrogen.

Medical Uses[edit]

Epitiostanol was primarily used in the treatment of breast cancer, particularly in postmenopausal women. Its ability to inhibit estrogen-dependent tumor growth made it a valuable therapeutic option before the advent of more modern treatments.

Pharmacokinetics[edit]

Epitiostanol is administered via injection due to its poor oral bioavailability. Once administered, it is metabolized in the liver and excreted primarily through the urine.

Side Effects[edit]

As with other anabolic-androgenic steroids, epitiostanol can cause a range of side effects. These may include:

Discontinuation[edit]

The use of epitiostanol has largely been discontinued in favor of newer, more effective treatments for breast cancer, such as tamoxifen and aromatase inhibitors.

Related Compounds[edit]

Epitiostanol is related to other anabolic-androgenic steroids, such as oxandrolone and stanozolol, which also have medical applications but differ in their specific uses and side effect profiles.

Related Pages[edit]

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-'''Epitiostanol''' is an [[androgen]] and [[anabolic steroid]] (AAS) medication and derivative of [[dihydrotestosterone]] (DHT) that is used in Japan to treat [[breast cancer]]. It is taken by [[mouth]].
+{{DISPLAYTITLE:Epitiostanol}}
-==Medical uses==
+== Overview ==
-Epitiostanol is used in the treatment of breast cancer. It has been found to be effective in the treatment of estrogen receptor-positive breast cancer, particularly in postmenopausal women. The drug works by inhibiting the effects of estrogen in the breast tissue, which can help to slow or stop the growth of certain types of breast cancer cells that require estrogen to grow.
+'''Epitiostanol''' is a synthetic anabolic-androgenic steroid (AAS) that was developed in the 1960s. It is primarily known for its use in the treatment of breast cancer. Epitiostanol is a derivative of [[dihydrotestosterone]] (DHT) and is characterized by its unique chemical structure, which includes a sulfur atom.
-==Pharmacology==
+== Chemical Structure ==
-===Pharmacodynamics===
+[[File:Epitiostanol.svg|thumb|right|Chemical structure of Epitiostanol]]
-As a derivative of dihydrotestosterone, epitiostanol has both androgenic and anabolic effects. It acts as an [[antiestrogen]] by its mechanism of action, competing with estrogen for receptor sites in target organs such as the breast. This competition can inhibit estrogen-mediated processes, including the growth of certain types of breast cancer cells. Unlike many other AAS, epitiostanol does not undergo aromatization, meaning it does not convert to estrogen in the body, which is beneficial in the context of treating estrogen receptor-positive breast cancer.
+Epitiostanol is chemically known as 2_,3_-epithio-5_-androstan-17_-ol. The presence of the epithio group (a sulfur atom replacing an oxygen atom) in its structure is a distinguishing feature that contributes to its biological activity.
-===Pharmacokinetics===
+== Mechanism of Action ==
-The pharmacokinetics of epitiostanol, including its absorption, distribution, metabolism, and excretion, are not well-documented in the scientific literature. However, as an oral medication, it is assumed to undergo first-pass metabolism in the liver, which may affect its bioavailability and overall effectiveness.
+Epitiostanol functions as an anti-estrogenic agent. It binds to [[estrogen receptor|estrogen receptors]] in breast tissue, thereby inhibiting the growth of estrogen-dependent tumors. Unlike other anti-estrogens, epitiostanol does not exhibit estrogenic activity, making it a pure anti-estrogen.
-==Adverse effects==
+== Medical Uses ==
-The adverse effects of epitiostanol are similar to those of other androgen and anabolic steroid medications. These can include masculinization, acne, and changes in liver function tests. Due to its antiestrogenic effects, it may also cause symptoms related to estrogen deficiency, such as hot flashes or osteoporosis, particularly with long-term use.
+Epitiostanol was primarily used in the treatment of [[breast cancer]], particularly in postmenopausal women. Its ability to inhibit estrogen-dependent tumor growth made it a valuable therapeutic option before the advent of more modern treatments.
-==Chemistry==
+== Pharmacokinetics ==
-Epitiostanol is a synthetic derivative of dihydrotestosterone, specifically, it is a 2α,3α-epithio derivative of DHT. This modification confers its antiestrogenic activity and distinguishes it from other AAS in terms of its mechanism of action and therapeutic use.
+Epitiostanol is administered via injection due to its poor oral bioavailability. Once administered, it is metabolized in the liver and excreted primarily through the urine.
-==History==
+== Side Effects ==
-Epitiostanol was developed and introduced for medical use in Japan. It has been used in the treatment of breast cancer for several decades and has contributed to the therapeutic options available for managing this disease, particularly in cases where estrogen plays a role in cancer progression.
+As with other anabolic-androgenic steroids, epitiostanol can cause a range of side effects. These may include:
+* [[Virilization]] in women
+* [[Liver toxicity]]
+* Changes in [[lipid profile]]
-==Society and culture==
+== Discontinuation ==
-===Legal status===
+The use of epitiostanol has largely been discontinued in favor of newer, more effective treatments for breast cancer, such as [[tamoxifen]] and [[aromatase inhibitors]].
-In Japan, epitiostanol is approved for medical use in the treatment of breast cancer. Its legal status in other countries may vary, and it is not widely used or available outside of Japan.
-==See also==
+== Related Compounds ==
-* [[List of androgen esters]]
+Epitiostanol is related to other anabolic-androgenic steroids, such as [[oxandrolone]] and [[stanozolol]], which also have medical applications but differ in their specific uses and side effect profiles.
-* [[Selective estrogen receptor modulator]]
-* [[Antiestrogen]]
-[[Category:Androgens and anabolic steroids]]
+== Related Pages ==
-[[Category:Antineoplastic drugs]]
+* [[Anabolic-androgenic steroid]]
-[[Category:Japanese inventions]]
+* [[Breast cancer treatment]]
-{{medicine-stub}}
+* [[Estrogen receptor]]
+[[Category:Anabolic-androgenic steroids]]
+[[Category:Breast cancer treatments]]