Structure–activity relationships of anabolic steroids: Difference between revisions

Latest revision as of 01:47, 7 March 2025

The structure–activity relationships (SAR) of anabolic steroids refer to the relationship between the chemical structure of anabolic steroids and their biological activity. Anabolic steroids are synthetic derivatives of the hormone testosterone, which is the primary male sex hormone and an anabolic steroid itself. These compounds are designed to enhance the anabolic effects (such as muscle growth) while minimizing androgenic effects (such as the development of male characteristics).

Chemical Structure[edit]

Anabolic steroids are characterized by a core structure of four fused carbon rings, known as the cyclopentanoperhydrophenanthrene ring system. This structure is shared with other steroids, including cholesterol and corticosteroids. Modifications to this core structure can significantly alter the activity of the steroid.

Modifications to the A-Ring[edit]

The A-ring of the steroid nucleus can be modified to enhance anabolic activity. For example, the introduction of a 1-dehydro modification (a double bond between carbon 1 and 2) can increase the anabolic to androgenic ratio. This modification is seen in steroids like nandrolone.

Modifications to the B-Ring[edit]

Alterations to the B-ring, such as the addition of a 9α-fluoro group, can also affect the activity of the steroid. These modifications can enhance the binding affinity to the androgen receptor, thereby increasing anabolic effects.

Modifications to the C-Ring[edit]

The C-ring can be modified by adding a 17α-alkyl group, which increases oral bioavailability by preventing hepatic metabolism. However, this modification can also increase hepatotoxicity, as seen in steroids like methandrostenolone.

Modifications to the D-Ring[edit]

The D-ring modifications, such as the addition of a 17β-hydroxy group, are crucial for the anabolic activity of the steroid. This group is essential for binding to the androgen receptor and is present in all active anabolic steroids.

Mechanism of Action[edit]

Anabolic steroids exert their effects by binding to the androgen receptor, a type of nuclear receptor that regulates gene expression. Upon binding, the steroid-receptor complex translocates to the cell nucleus, where it binds to specific DNA sequences, leading to the transcription of genes involved in muscle growth and other anabolic processes.

Clinical Applications[edit]

Anabolic steroids are used clinically to treat conditions such as hypogonadism, delayed puberty, and muscle wasting diseases. They are also used illicitly to enhance athletic performance and physical appearance.

Adverse Effects[edit]

The use of anabolic steroids can lead to a range of adverse effects, including liver damage, cardiovascular disease, and endocrine disorders. The risk of these effects is increased with higher doses and prolonged use.

Related Pages[edit]

@@ Line 1: / Line 1: @@
 {{DISPLAYTITLE:Structure–activity relationships of anabolic steroids}}
-== Overview ==
+[[File:Testosteron.svg|Testosterone molecule structure|thumb|right]]
-The '''structure–activity relationships''' (SAR) of [[anabolic steroids]] are critical in understanding how modifications to the chemical structure of these compounds can influence their biological activity. Anabolic steroids are synthetic derivatives of [[testosterone]], designed to enhance anabolic effects such as muscle growth while minimizing androgenic effects.
-== Chemical Structure ==
+The '''structure–activity relationships (SAR) of anabolic steroids''' refer to the relationship between the chemical structure of anabolic steroids and their biological activity. Anabolic steroids are synthetic derivatives of the hormone [[testosterone]], which is the primary male sex hormone and an anabolic steroid itself. These compounds are designed to enhance the anabolic effects (such as muscle growth) while minimizing androgenic effects (such as the development of male characteristics).
-Anabolic steroids are characterized by their core structure, which is based on the [[cyclopentanoperhydrophenanthrene]] ring system. This structure consists of three six-membered carbon rings (A, B, and C) and one five-membered carbon ring (D).
-[[File:Testosteron.svg|Testosterone structure|thumb|right]]
+==Chemical Structure==
+Anabolic steroids are characterized by a core structure of four fused carbon rings, known as the cyclopentanoperhydrophenanthrene ring system. This structure is shared with other [[steroids]], including [[cholesterol]] and [[corticosteroids]]. Modifications to this core structure can significantly alter the activity of the steroid.
-=== Modifications ===
+===Modifications to the A-Ring===
-Modifications to the steroid nucleus can significantly alter the activity of anabolic steroids. These modifications can occur at various positions on the steroid backbone:
+The A-ring of the steroid nucleus can be modified to enhance anabolic activity. For example, the introduction of a 1-dehydro modification (a double bond between carbon 1 and 2) can increase the anabolic to androgenic ratio. This modification is seen in steroids like [[nandrolone]].
-* '''A-ring modifications''': Alterations to the A-ring, such as the introduction of a 1-dehydro group, can enhance anabolic activity.
+===Modifications to the B-Ring===
-* '''B-ring modifications''': Changes to the B-ring, such as the addition of a 9α-fluoro group, can increase both anabolic and androgenic activity.
+Alterations to the B-ring, such as the addition of a 9α-fluoro group, can also affect the activity of the steroid. These modifications can enhance the binding affinity to the androgen receptor, thereby increasing anabolic effects.
-* '''C-ring modifications''': The introduction of a 17α-alkyl group can increase oral bioavailability but also increase hepatotoxicity.
-* '''D-ring modifications''': Modifications such as the addition of a 17β-hydroxy group are crucial for receptor binding and activity.
-== Mechanism of Action ==
+===Modifications to the C-Ring===
-Anabolic steroids exert their effects by binding to the [[androgen receptor]] (AR), a type of nuclear receptor that regulates gene expression. Upon binding, the steroid-receptor complex translocates to the cell nucleus, where it binds to specific DNA sequences, leading to the transcription of genes involved in muscle growth and other anabolic processes.
+The C-ring can be modified by adding a 17α-alkyl group, which increases oral bioavailability by preventing hepatic metabolism. However, this modification can also increase hepatotoxicity, as seen in steroids like [[methandrostenolone]].
-== Anabolic vs. Androgenic Effects ==
+===Modifications to the D-Ring===
-The distinction between anabolic and androgenic effects is a key consideration in the development of anabolic steroids. Anabolic effects include increased protein synthesis, muscle mass, and bone density, while androgenic effects involve the development of male secondary sexual characteristics.
+The D-ring modifications, such as the addition of a 17β-hydroxy group, are crucial for the anabolic activity of the steroid. This group is essential for binding to the androgen receptor and is present in all active anabolic steroids.
-=== Selectivity ===
+[[File:Trimethyl_steroid-nomenclature.svg|Steroid nomenclature|thumb|left]]
-The goal of modifying anabolic steroids is to maximize anabolic effects while minimizing androgenic effects. This selectivity is achieved through structural modifications that enhance binding affinity for the AR in muscle tissue compared to other tissues.
+==Mechanism of Action==
+Anabolic steroids exert their effects by binding to the [[androgen receptor]], a type of nuclear receptor that regulates gene expression. Upon binding, the steroid-receptor complex translocates to the cell nucleus, where it binds to specific DNA sequences, leading to the transcription of genes involved in muscle growth and other anabolic processes.
-== Clinical Applications ==
+==Clinical Applications==
-Anabolic steroids are used clinically to treat conditions such as muscle wasting in chronic illness, delayed puberty, and certain types of anemia. However, their use is often limited by potential side effects and the risk of abuse.
+Anabolic steroids are used clinically to treat conditions such as [[hypogonadism]], delayed puberty, and muscle wasting diseases. They are also used illicitly to enhance athletic performance and physical appearance.
-== Side Effects ==
+==Adverse Effects==
-The use of anabolic steroids can lead to a range of side effects, including liver damage, cardiovascular issues, and endocrine disturbances. The risk of side effects is influenced by the specific structure of the steroid and the route of administration.
+The use of anabolic steroids can lead to a range of adverse effects, including liver damage, cardiovascular disease, and endocrine disorders. The risk of these effects is increased with higher doses and prolonged use.
-== Related Pages ==
+==Related Pages==
 * [[Anabolic steroid]]
 * [[Testosterone]]
 * [[Androgen receptor]]
 * [[Steroid hormone]]
-[[File:Trimethyl_steroid-nomenclature.svg|Steroid nomenclature|thumb|left]]
 [[Category:Anabolic steroids]]
 [[Category:Pharmacology]]
-[[Category:Steroid chemistry]]