Metandienone Wikipedia

Metandienone (also known as methandrostenolone or Dianabol) is an anabolic–androgenic steroid (AAS) derived from testosterone. It was first synthesized in 1951 and marketed by the pharmaceutical company Searle for the treatment of muscle wasting, osteoporosis, and certain forms of anemia. The compound gained notoriety among athletes and bodybuilders during the 1970s due to its ability to enhance lean muscle mass and improve strength.



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Chemical Profile


Property Value


Molecular Formula C₂₀H₂₉O₂


Molecular Weight 317.45 g/mol


IUPAC Name (5S,8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,4,6,7,8,9,11,12,14,15,16,17‑dodecahydro‑1H‑cyclopenta[a]phenanthren‑17‑yl acetate


CAS Number 56‑02‑5


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3. Structural Features & Implications



Feature Details Functional Consequence


Acetate ester at C17β Esterification of the secondary alcohol at C17 (position in steroids). Increases lipophilicity → better membrane permeability and oral bioavailability.


Steroid nucleus (cyclopenta‑aphenanthrene) Four fused rings, typical for endogenous steroids. Provides structural scaffold recognized by steroid receptors; high metabolic stability.


No additional polar groups Apart from the ester, no hydroxyls or carboxylates. Enhances passive diffusion across lipid bilayers; reduces renal clearance.


Hydrophobic side chain (ethyl group) Present at C17. Contributes to overall lipophilicity and binding affinity to receptors.


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How these properties influence its use




High oral bioavailability – due to strong lipophilicity and limited first‑pass metabolism.


Prolonged systemic presence – ester hydrolysis releases the active compound slowly, extending therapeutic effect.


Reduced renal excretion – minimal polar groups limit glomerular filtration and tubular secretion.



Thus, the chemical structure of DHEA, characterized by its lipophilic framework and ester functionality, underpins its pharmacokinetic profile and makes it suitable for oral administration in therapeutic settings.