Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H28O2 |
| Molecular Weight | 276.4137 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O)CC[C@H]34)[C@@H]1CC[C@@H]2O
InChI
InChIKey=CMXKUJNZWYTFJN-XFUVECHXSA-N
InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1
| Molecular Formula | C18H28O2 |
| Molecular Weight | 276.4137 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Bolandiol (INN), also known as 19-nor-4-androstenediol, estr-4-en-3β,17β-diol, or 3β-dihydronandrolone, is an anabolic-androgenic steroid (AAS) that was never marketed. Bolandiol bound with lower affinity to the recombinant rat androgen receptor (AR) than the other androgens and had low, but measurable, affinity for recombinant human progestin receptors (PR-A, PR-B), and estrogen receptors (ERalpha and beta-1). Functional agonist activity was assessed in transcription assays mediated by AR, PR, or ER. Bolandiol that until recently was available as a dietary supplement used by athletes to enhance performance. 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 to nandrolone. However, several clinical studies have concluded that bolandiol does not alter the strength, body composition, or exercise performance. Bolandiol suppresses gonadotropins and endogenous testosterone production.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of the oestrogenic activity of non-aromatic steroids: are there male-specific endogenous oestrogen receptor modulators? | 2009-12 |
|
| Detection and quantification of glucuro- and sulfoconjugated metabolites in human urine following oral administration of xenobiotic 19-norsteroids. | 2006-09 |
|
| Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. | 2005-03 |
|
| Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. | 2004-07 |
Patents
| Substance Class |
Chemical
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| Record UNII |
49SD6G16U5
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Validated (UNII)
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DEA NO. |
4000
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m2595
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DB01554
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SUB05866MIG
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C166743
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BOLANDIOL
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ACTIVE MOIETY |