Page last updated: 2024-11-06

5-alpha-dihydroprogesterone

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

Description

5-alpha-Dihydroprogesterone: A biologically active 5-alpha-reduced metabolite of plasma PROGESTERONE. It is the immediate precursor of 5-alpha-pregnan-3-alpha-ol-20-one (ALLOPREGNANOLONE), a neuroactive steroid that binds with GABA(A) RECEPTOR. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

5alpha-pregnane-3,20-dione : A C21-steroid hormone that is 5alpha-pregnane substituted by oxo groups at positions 3 and 20. It is a metabolite of progestrone. [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 CID92810
CHEMBL ID407717
CHEBI ID28952
SCHEMBL ID37778
MeSH IDM0044565

Synonyms (69)

Synonym
BIDD:PXR0089
5b-pregnane-3,20-dione
3,20-dioxo-5alpha-pregnane
CHEBI:28952 ,
5-alpha-dihydroprogesterone
pregnane-3,20-dione, (5.alpha.)-
5.alpha.-dihydroprogesterone
nsc-18319
wln: l e5 b666 ovtj a1 e1 fv1
nsc18319
5.alpha.-pregnane-3,20-dione
3,20-dioxo-5.alpha.-pregnane
3,20-allopregnanedione
pregnane-3, (5.alpha.)-
brn 2058506
einecs 209-297-3
nsc 18319
pregnane-3,20-dione, (5alpha)-
allopregnan-3,20-dione
C03681
5alpha-pregnane-3,20-dione
566-65-4
5alpha-dihydroprogesterone
5alpha-pregnane-3,20-dione (allo), progesterone metabolite
pregnane-3,20-dione, 5alpha-allo-
4C28DCDC-9872-4488-85F5-6D25C01E9A45
5alpha-pregnan-3,20-dione
5alpha-pregnane-3,20-dione (allo)
BMSE000490
allopregnane-3,20-dione
CHEMBL407717 ,
5alpha-pregnandione
LMST02030170
(5s,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
A8107
5a-pregnane-3,20-dione
4-07-00-02199 (beilstein handbook reference)
unii-98g4s1oh0z
98g4s1oh0z ,
S3206
allo-pregnandione
allopregnandione
5 a-pregnane-3,20-dione
5alpha-pregnane-3,20-dione(allo)
5 a-pregnane-3 20-dione
bdbm50375561
AKOS015895181
3,20-allopregnanedione [mi]
(5.alpha.)-pregnane-3,20-dione
5alpha-pregnan-3,20 -dione
5alpha-pregnane 3,20-dione
SCHEMBL37778
(5s,8r,9s,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
(5?)-pregnane-3,20-dione
pregnane-3,20-dione, (5a)-
5.alpha.-pregnan-3,20-dione
CS-W006492
5a-dihydroprogesterone
5a-pregnan-3,20-dione
3,20-dioxo-5a-pregnane
(5alpha)-pregnane-3,20-dione
HY-W006492
Q28487660
AS-15992
DTXSID301017277
allodihydroprogeserone
PD099522
5f inverted question mark-pregnane-3,20-dione
P2423

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
"1-1 microM) of muscimol, and the muscimol dose-response (0."( Brain allopregnanolone regulates the potency of the GABA(A) receptor agonist muscimol.
Costa, E; Guidotti, A; Matsumoto, K; Mienville, JM; Pinna, G; Puia, G; Uzunova, V, 2000
)
0.31
" This is a novel site of action for fluoxetine, with implications for the development of new agents and/or dosing regimens to raise brain allopregnanolone."( Fluoxetine elevates allopregnanolone in female rat brain but inhibits a steroid microsomal dehydrogenase rather than activating an aldo-keto reductase.
Cockcroft, S; Devall, AJ; Fry, JP; Honour, JW; Li, KY; Lovick, TA, 2014
)
0.4
[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).
progestogenA compound that interacts with progesterone receptors in target tissues to bring about effects similar to those of progesterone.
[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-steroid hormoneA steroid compound with a structure based on a 21-carbon (pregnane) skeleton that acts as a hormone.
3-oxo-5alpha-steroidA 3-oxo steroid that has alpha 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 (14)

PathwayProteinsCompounds
Steroidogenesis1142
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase Deficiency1142
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAH1142
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase Deficiency1142
17-alpha-Hydroxylase Deficiency (CYP17)1142
11-beta-Hydroxylase Deficiency (CYP11B1)1142
21-Hydroxylase Deficiency (CYP21)1142
Corticosterone Methyl Oxidase I Deficiency (CMO I)1142
Corticosterone Methyl Oxidase II Deficiency (CMO II)1142
Apparent Mineralocorticoid Excess Syndrome1142
3-beta-Hydroxysteroid Dehydrogenase Deficiency1142
cardenolide biosynthesis17
Steroid hormone precursor biosynthesis015
allopregnanolone biosynthesis66

Protein Targets (1)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
G-protein coupled bile acid receptor 1Homo sapiens (human)EC50 (µMol)0.29000.02372.52598.9000AID324923
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (6)

Processvia Protein(s)Taxonomy
cell surface bile acid receptor signaling pathwayG-protein coupled bile acid receptor 1Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeG-protein coupled bile acid receptor 1Homo sapiens (human)
cellular response to bile acidG-protein coupled bile acid receptor 1Homo sapiens (human)
positive regulation of cholangiocyte proliferationG-protein coupled bile acid receptor 1Homo sapiens (human)
regulation of bicellular tight junction assemblyG-protein coupled bile acid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwayG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
protein bindingG-protein coupled bile acid receptor 1Homo sapiens (human)
bile acid receptor activityG-protein coupled bile acid receptor 1Homo sapiens (human)
G protein-coupled bile acid receptor activityG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
cytoplasmG-protein coupled bile acid receptor 1Homo sapiens (human)
plasma membraneG-protein coupled bile acid receptor 1Homo sapiens (human)
receptor complexG-protein coupled bile acid receptor 1Homo sapiens (human)
plasma membraneG-protein coupled bile acid receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
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.
AID324923Agonist activity at human TGR5 expressed in CHO cells by luciferase assay2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
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.
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.
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.
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.
AID81741Dose that required to inhibit cell growth for cytotoxicity against HEp-2 cells in culture1980Journal of medicinal chemistry, Jan, Volume: 23, Issue:1
Steroidal alpha-methylene delta-lactones as potential antitumor agents.
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.
AID324924Agonist activity at human TGR5 expressed in CHO cells by luciferase assay relative to lithocholic acid2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Novel potent and selective bile acid derivatives as TGR5 agonists: biological screening, structure-activity relationships, and molecular modeling studies.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (148)

TimeframeStudies, This Drug (%)All Drugs %
pre-199028 (18.92)18.7374
1990's38 (25.68)18.2507
2000's47 (31.76)29.6817
2010's30 (20.27)24.3611
2020's5 (3.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.13

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.13 (24.57)
Research Supply Index5.04 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.13)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (1.31%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (0.65%)0.25%
Other150 (98.04%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]