Bolandiol

Bolandiol (INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.

Chemical data

Formula: C18H28O2
Molecular weight: 276.4 g/mol
IUPAC name: (3S,8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C[C@H](CC[C@H]34)O
InChIKey: CMXKUJNZWYTFJN-XFUVECHXSA-N
XLogP: 2.7
Polar surface area: 40.5 Å²
H-bond donors: 2
H-bond acceptors: 2
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule

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Wikidata facts

Mass: 276.208930136

Show 3 more facts

chemical formula: C₁₈H₂₈O₂
isomeric SMILES: O[C@@H]4/C=C2\[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4
canonical SMILES: CC12CCC3C4CCC(O)C=C4CCC3C1CCC2O

Sources (2)

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Encyclopedic overview

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Contents

See also
References

Bolandiol is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports. It is a potential metabolic precursor (via 3β-HSD) to nandrolone or a derivative of nandrolone (via 3β-hydroxy-steroid:NADP+ 3-oxidoreductase). However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.

Excerpted from Wikipedia’s “Bolandiol” article, available under the CC BY-SA 4.0 licence.

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