Page last updated: 2024-11-06

5beta-pregnane-3,20-dione

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

5beta-Pregnane-3,20-dione, also known as allopregnanolone, is a naturally occurring neurosteroid with potent anxiolytic and sedative effects. It is a metabolite of progesterone and is produced in the brain and other tissues. Allopregnanolone acts as a positive allosteric modulator of the GABA-A receptor, enhancing the effects of GABA, the primary inhibitory neurotransmitter in the brain. Its synthesis involves the reduction of progesterone by the enzyme 5alpha-reductase. Research suggests that allopregnanolone may be involved in the regulation of mood, sleep, and stress responses. Its role in conditions such as anxiety, depression, and epilepsy is being investigated. The study of allopregnanolone is important due to its potential therapeutic applications as an anxiolytic and sedative agent. It is also a target for drug development in the treatment of neuropsychiatric disorders.'
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5beta-pregnane-3,20-dione : A C21-steroid that is 5beta-pregnane with oxo groups at positions 3 and 20. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID92745
CHEMBL ID486954
CHEBI ID30154
SCHEMBL ID675417

Synonyms (45)

Synonym
BIDD:PXR0013
gtpl2759
5beta-dihydroprogesterone
5beta-pregnan-3,20-dione
CHEBI:30154 ,
3,20-pregnanedione
pregnane-3,20-dione, (5.beta.)-
nsc-82868
5.beta.-pregnan-3,20-dione
nsc82868
5.beta.-dihydroprogesterone
pregnane-3, (5.beta.)-
pregnane-3,20-dione, (5beta)-
nsc 82868
5beta-pregnane-3,20-dione
C05479
128-23-4
(5beta)-pregnane-3,20-dione
5beta-pregnan-3,20 dione
pregnane-3,20-dione, 5beta-
E15E6736-8300-4A12-A6C4-36A77193C0BE
DB07557
CHEMBL486954
LMST02030146
(5r,8r,9s,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
A806097
(5r,8r,9s,10s,13s,14s,17s)-17-ethanoyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
105j2q45a0 ,
unii-105j2q45a0
pregnane-3,20-dione, (5b)-
SCHEMBL675417
3,20-pregnanedione [mi]
u-2411
J-005574
5beta-dihydro progesterone
5|a-dihydro progesterone
(5alpha,8alpha,10alpha,14beta,17alpha)-pregnane-3,20-dione
Q21099648
5 beta -dihydro progesterone
5b-dihydroprogesterone
DTXSID00878589
5?-dihydro progesterone
(5r,8s,9s,10r,13s,14s,17s)-17-acetyl-5,10,13-trimethylhexadecahydro-3h-cyclopenta[a]phenanthren-3-one
LCZC3860
5-beta-pregnan-3,20 dione
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
20-oxo steroidAn oxo steroid carrying an oxo group at position 20.
C21-steroidA steroid that has a structure based on a 21-carbon (pregnane) skeleton. Note that individual examples may have ring substituents at other positions and/or contain double bonds, aromatic A-rings, expanded/contracted rings etc., so the formula and mass may vary from that given for the generic structure.
3-oxo-5beta-steroidAny 3-oxo steroid that has beta- configuration at position 5.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (3)

PathwayProteinsCompounds
cardenolide biosynthesis17
Steroid hormone precursor biosynthesis015
Classical pathway of steroidogenesis with glucocorticoid and mineralocorticoid metabolism325

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1150121Relative binding affinity to human progesterone receptor1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Quantitative relationships between steroid structure and binding to putative progesterone receptors.
AID681167TP_TRANSPORTER: Northern blot from LS174T cell2001The Journal of biological chemistry, May-04, Volume: 276, Issue:18
Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin.
AID1150122Relative binding affinity to sheep progesterone receptor1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Quantitative relationships between steroid structure and binding to putative progesterone receptors.
AID345825Activation of human CAR-LBD expressed in human C3A cells at 10 uM after 24 hrs by GAL4-dependent luciferase reporter gene assay relative to control2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Insights into ligand-elicited activation of human constitutive androstane receptor based on novel agonists and three-dimensional quantitative structure-activity relationship.
AID1199781Inhibition of p-gp (unknown origin) in doxorubicin-resistant human K562/R7 cells assessed as increase in daunorubicin accumulation measured as fluorescence ratio at 10 uM incubated for 1 hr with 10 uM daunorubicin by flow cytometry relative to control2015Journal of medicinal chemistry, Feb-26, Volume: 58, Issue:4
Synthesis of new steroidal inhibitors of P-glycoprotein-mediated multidrug resistance and biological evaluation on K562/R7 erythroleukemia cells.
AID1150124Relative binding affinity to guinea pig progesterone receptor1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Quantitative relationships between steroid structure and binding to putative progesterone receptors.
AID50906Inhibition of mouse constitutive androstane receptor (mCAR) activity at 10 uM was determined as percent remaining activity2003Journal of medicinal chemistry, Oct-23, Volume: 46, Issue:22
Molecular determinants of steroid inhibition for the mouse constitutive androstane receptor.
AID345924Increase in human nuclear co-repressor receptor binding to human CAR-LBD expressed in HEK293 cells by yeast two-hybrid assay2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Insights into ligand-elicited activation of human constitutive androstane receptor based on novel agonists and three-dimensional quantitative structure-activity relationship.
AID1150123Relative binding affinity to rabbit progesterone receptor1977Journal of medicinal chemistry, Sep, Volume: 20, Issue:9
Quantitative relationships between steroid structure and binding to putative progesterone receptors.
AID345923Increase in human steroid receptor coactivator 1 binding to human CAR-LBD expressed in human C3A cells by mammalian two-hybrid assay2008Journal of medicinal chemistry, Nov-27, Volume: 51, Issue:22
Insights into ligand-elicited activation of human constitutive androstane receptor based on novel agonists and three-dimensional quantitative structure-activity relationship.
AID1346741Human Pregnane X receptor (1I. Vitamin D receptor-like receptors)2000Molecular endocrinology (Baltimore, Md.), Jan, Volume: 14, Issue:1
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.
AID1346746Human Constitutive androstane receptor (1I. Vitamin D receptor-like receptors)2000The Journal of biological chemistry, May-19, Volume: 275, Issue:20
Orphan nuclear receptors constitutive androstane receptor and pregnane X receptor share xenobiotic and steroid ligands.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's0 (0.00)18.2507
2000's5 (71.43)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.51

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.51 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]