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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
Structure of BOLANDIOL

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CC[C@H](O)C=C4CC[C@@]23[H]

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

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements.
2004 Jul
Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids.
2005 Mar
Detection and quantification of glucuro- and sulfoconjugated metabolites in human urine following oral administration of xenobiotic 19-norsteroids.
2006 Sep
Characterization of the oestrogenic activity of non-aromatic steroids: are there male-specific endogenous oestrogen receptor modulators?
2009 Dec
Patents

Patents

Name Type Language
BOLANDIOL
INN   MART.   MI  
INN  
Official Name English
ESTR-4-ENE-3,17-DIOL, (3.BETA.,17.BETA.)-
Systematic Name English
19-NOR-4-ANDROSTENE-3.BETA.0,17.BETA.-DIOL
Systematic Name English
4-NORENDIOL
Common Name English
BOLANDIOL [MI]
Common Name English
(3.BETA.,17.BETA.)-ESTR-4-ENE-3,17-DIOL
Systematic Name English
bolandiol [INN]
Common Name English
19-NOR-4-ANDROSTENEDIOL
Common Name English
3BETA,17BETA-DIHYDROXYESTR-4-ENE
Systematic Name English
BOLANDIOL [MART.]
Common Name English
3.BETA.,17.BETA.-DIHYDROXYESTR-4-ENE
Systematic Name English
Classification Tree Code System Code
DEA NO. 4000
Created by admin on Sat Dec 16 10:14:41 GMT 2023 , Edited by admin on Sat Dec 16 10:14:41 GMT 2023
Code System Code Type Description
MERCK INDEX
m2595
Created by admin on Sat Dec 16 10:14:41 GMT 2023 , Edited by admin on Sat Dec 16 10:14:41 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB01554
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PRIMARY
EVMPD
SUB05866MIG
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PRIMARY
NCI_THESAURUS
C166743
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PRIMARY
WIKIPEDIA
BOLANDIOL
Created by admin on Sat Dec 16 10:14:41 GMT 2023 , Edited by admin on Sat Dec 16 10:14:41 GMT 2023
PRIMARY
CAS
19793-20-5
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PRIMARY
MESH
C547640
Created by admin on Sat Dec 16 10:14:41 GMT 2023 , Edited by admin on Sat Dec 16 10:14:41 GMT 2023
PRIMARY
FDA UNII
49SD6G16U5
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PRIMARY
CHEBI
145661
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PRIMARY
PUBCHEM
9835303
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PRIMARY
ChEMBL
CHEMBL2106664
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PRIMARY
EPA CompTox
DTXSID9041027
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PRIMARY
INN
2094
Created by admin on Sat Dec 16 10:14:41 GMT 2023 , Edited by admin on Sat Dec 16 10:14:41 GMT 2023
PRIMARY
SMS_ID
100000086326
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PRIMARY