Page last updated: 2024-09-20

etiocholanolone

Description

Etiocholanolone: The 5-beta-reduced isomer of ANDROSTERONE. Etiocholanolone is a major metabolite of TESTOSTERONE and ANDROSTENEDIONE in many mammalian species including humans. It is excreted in the URINE. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

3alpha-hydroxy-5beta-androstan-17-one : An androstanoid that is 5beta-androstane substituted by an alpha-hydroxy group at position 3 and an oxo group at position 17. It is a metabolite of testosterone in mammals. [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 CID5880
CHEMBL ID85799
CHEBI ID28195
SCHEMBL ID148334
MeSH IDM0007926

Synonyms (74)

Synonym
5b-androsterone
etiocholanone
CHEMBL85799 ,
5beta-androstan-3alpha-ol-17-one
(3alpha,5beta)-3-hydroxyandrostan-17-one
3alpha-etiocholanolone
CHEBI:28195 ,
5beta-androsterone
5-isoandrosterone
5.beta.-androstan-17-one, 3.alpha.-hydroxy-
nsc50908
5.beta.-androsterone
androstan-17-one, (3.alpha.,5.beta.)-
androsterone, (5.beta.)-
nsc-50908
etiocholan-3.alpha.-ol-17-one
3.alpha.-etiocholanolone
LMST02020059
3-alpha-hydroxy-5-beta-androstan-17-one ,
MLS001332472
MLS001332471
smr000857108
aetiocholanolone
3alpha-hydroxy-5beta-androstane-17-one
5beta-androstan-17-one, 3alpha-hydroxy-
5beta-androstane-3alpha-ol-17-one
androsterone, (5beta)-
AE2 ,
alpha-etiocholanolone
androstan-17-one, 3-hydroxy-, (3alpha,5beta)-
3alpha-hydroxyetiocholan-17-one
53-42-9
etiocholanolone
etiocholan-3alpha-ol-17-one
C04373
3alpha-hydroxy-5beta-androstan-17-one
DB02854
1DBJ
3-alpha-hydroxy-5-beta-androstane-17-one
bdbm50191348
MLS000563093
(3r,5r,8r,9s,10s,13s,14s)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
HMS2231A23
5 beta androsterone
unii-97cgb1m48i
97cgb1m48i ,
nsc 50908
AKOS015895180
j4.146g ,
.alpha.-etiocholanolone
3.alpha.-hydroxy-5.beta.-androstan-17-one
SCHEMBL148334
QGXBDMJGAMFCBF-BNSUEQOYSA-N
androstan-17-one,3-hydroxy-, (3a,5b)-
5.beta.-androstan-3.alpha.-ol-17-one
3-hydroxyandrostan-17-one-, (3.alpha.,5.beta.)-
3a-hydroxy-5b-androstan-17-one
etiocholan-3alpha-ol-17-one, vetranal(tm), analytical standard
atiocholanolon
NCGC00485031-01
a-etiocholanolone
5b-androstane-3a-ol-17-one
3a-etiocholanolone
5b-androstan-3a-ol-17-one
3a-hydroxy-5b-androstane-17-one
(3alpha,5beta,8alpha)-3-hydroxyandrostan-17-one
Q5404598
DTXSID001018919
(3r,5r,8r,10s,13s)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
MS-24148
HY-113320
CS-0059589
androstan-17-one, 3-hydroxy-, (3a,5b)-
(3as,3br,5ar,7r,9as,9bs,11as)-7-hydroxy-9a,11a-dimethyl-hexadecahydro-1h-cyclopenta[a]phenanthren-1-one

Research Excerpts

Overview

ExcerptReference
"Etiocholanolone is a physiologically occurring metabolite of testosterone and androstenedione which are secreted by adrenals, testes, and ovaries. "( Bedbur, M; Goerz, G; Graef, V, 1981)

Effects

ExcerptReference
"Etiocholanolone levels have been measured in both premastectomy and postoperative urines from 86 women with early breast cancer. "( Hamilton, T; Miller, WR; Prescott, RJ, 1978)

Treatment

ExcerptReference
"Etiocholanolone treatment of rats was ineffective in generation of a porphyria."( Golf, SW; Graef, V; Tyrell, C, 1982)

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
3alpha-hydroxy steroidA 3-hydroxy steroid in which the 3-hydroxy substituent is in the alpha-position.
17-oxo steroidAny oxo steroid carrying the oxo group at position 17.
androstanoidAny steroid based on an androstane skeleton and its derivatives.
[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 (5)

etiocholanolone is involved in 5 pathway(s), involving a total of 32 unique proteins and 1022 unique compounds

PathwayProteinsCompounds
Androstenedione Metabolism1823
Renz2020 - GEM of Human alveolar macrophage with SARS-CoV-20490
Male steroid hormones in cardiomyocyte energy metabolism1119
Biochemical pathways: part I0466
Heme synthesis324

Protein Targets (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency50.11870.044717.8581100.0000AID485294
ClpPBacillus subtilisPotency31.62281.995322.673039.8107AID651965
TDP1 proteinHomo sapiens (human)Potency11.83390.000811.382244.6684AID686978; AID686979
Smad3Homo sapiens (human)Potency6.30960.00527.809829.0929AID588855
gemininHomo sapiens (human)Potency0.25320.004611.374133.4983AID624296; AID624297
Guanine nucleotide-binding protein GHomo sapiens (human)Potency8.91251.995325.532750.1187AID624288
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain H, IGG1-KAPPA DB3 FAB (HEAVY CHAIN)Mus musculus (house mouse)IC50 (µMol)0.02100.00800.01450.0210AID977608
Chain L, IGG1-KAPPA DB3 FAB (LIGHT CHAIN)Mus musculus (house mouse)IC50 (µMol)0.02100.00800.01450.0210AID977608
Chain H, IGG1-KAPPA DB3 FAB (HEAVY CHAIN)Mus musculus (house mouse)IC50 (µMol)0.02100.00800.01450.0210AID977608
Chain L, IGG1-KAPPA DB3 FAB (LIGHT CHAIN)Mus musculus (house mouse)IC50 (µMol)0.02100.00800.01450.0210AID977608
Chain H, IGG1-KAPPA DB3 FAB (HEAVY CHAIN)Mus musculus (house mouse)IC50 (µMol)0.02100.00800.01450.0210AID977608
Chain L, IGG1-KAPPA DB3 FAB (LIGHT CHAIN)Mus musculus (house mouse)IC50 (µMol)0.02100.00800.01450.0210AID977608
Corticosteroid-binding globulinHomo sapiens (human)Ki5.88840.01323.248110.0000AID51055
Testosterone 17-beta-dehydrogenase 3Homo sapiens (human)IC50 (µMol)0.29300.00261.76469.3000AID215943; AID215945; AID215947; AID242395
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sex hormone-binding globulinHomo sapiens (human)Kd0.70790.00020.34964.7863AID318680
G-protein coupled bile acid receptor 1Homo sapiens (human)EC50 (µMol)3.76000.02372.52598.9000AID324923
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
glucocorticoid metabolic processCorticosteroid-binding globulinHomo sapiens (human)
negative regulation of endopeptidase activityCorticosteroid-binding globulinHomo sapiens (human)
androgen biosynthetic processTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
male genitalia developmentTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
testosterone biosynthetic processTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
steroid biosynthetic processTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
negative regulation of inflammatory response to antigenic stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
renal water homeostasisGuanine nucleotide-binding protein GHomo sapiens (human)
G protein-coupled receptor signaling pathwayGuanine nucleotide-binding protein GHomo sapiens (human)
regulation of insulin secretionGuanine nucleotide-binding protein GHomo sapiens (human)
cellular response to glucagon stimulusGuanine nucleotide-binding protein GHomo sapiens (human)
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 (12)

Processvia Protein(s)Taxonomy
androgen bindingSex hormone-binding globulinHomo sapiens (human)
protein bindingSex hormone-binding globulinHomo sapiens (human)
steroid bindingSex hormone-binding globulinHomo sapiens (human)
steroid bindingCorticosteroid-binding globulinHomo sapiens (human)
serine-type endopeptidase inhibitor activityCorticosteroid-binding globulinHomo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activityTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
testosterone dehydrogenase [NAD(P)] activityTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activityTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
17-beta-hydroxysteroid dehydrogenase (NADP+) activityTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
G protein activityGuanine nucleotide-binding protein GHomo sapiens (human)
adenylate cyclase activator activityGuanine nucleotide-binding protein GHomo sapiens (human)
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 (9)

Processvia Protein(s)Taxonomy
extracellular regionSex hormone-binding globulinHomo sapiens (human)
extracellular exosomeSex hormone-binding globulinHomo sapiens (human)
extracellular regionCorticosteroid-binding globulinHomo sapiens (human)
extracellular spaceCorticosteroid-binding globulinHomo sapiens (human)
extracellular exosomeCorticosteroid-binding globulinHomo sapiens (human)
extracellular spaceCorticosteroid-binding globulinHomo sapiens (human)
endoplasmic reticulumTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
endoplasmic reticulum membraneTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
intracellular membrane-bounded organelleTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
endoplasmic reticulumTestosterone 17-beta-dehydrogenase 3Homo sapiens (human)
plasma membraneGuanine nucleotide-binding protein GHomo sapiens (human)
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 (65)

Assay IDTitleYearJournalArticle
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID215948Percent inhibition against type-3 17-beta-HSD expressed in HEK293 cells at 0.3 uM2000Bioorganic & medicinal chemistry letters, Nov-20, Volume: 10, Issue:22
Androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase.
AID624616Specific activity of expressed human recombinant UGT2B152000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID51062In silico steroid binding affinity to transport protein corticosteroid binding globulin1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
Compass: predicting biological activities from molecular surface properties. Performance comparisons on a steroid benchmark.
AID220020Binding affinity towards human corticosteroid binding globulin.1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
QSAR's from similarity matrices. Technique validation and application in the comparison of different similarity evaluation methods.
AID266558Activity at rat GABA-Aalpha1 receptor plus beta-2-gamma-2L expressed in Xenopus laevis oocyte assessed as ratio of GABA-mediated current in presence to absence of GABA at 10 uM2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
AID318680Displacement of [3H]5alpha dihydrotestosterone from human sex hormone binding globulin2008Journal of medicinal chemistry, Apr-10, Volume: 51, Issue:7
An updated steroid benchmark set and its application in the discovery of novel nanomolar ligands of sex hormone-binding globulin.
AID382395Anesthetic effect in Xenopus laevis assessed as loss of swimming response at 10 uM2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID266555Activity at rat GABA-Aalpha1 receptor plus beta-2-gamma-2L expressed in Xenopus laevis oocyte assessed as ratio of GABA-mediated current in presence to absence of compound at 0.1 uM2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
AID212920Binding affinity against transport protein testosterone binding globulin.1994Journal of medicinal chemistry, Jul-22, Volume: 37, Issue:15
Compass: predicting biological activities from molecular surface properties. Performance comparisons on a steroid benchmark.
AID266562Loss of swimming reflex in Xenopus laevis tadpole at 10 uM2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
AID51054Binding affinity for corticosteroid binding globulin is expressed as log(1/k)1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Comparative molecular moment analysis (CoMMA): 3D-QSAR without molecular superposition.
AID624619Specific activity of expressed human recombinant UGT2B72000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
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.
AID266556Activity at rat GABA-Aalpha1 receptor plus beta2gamma2L expressed in Xenopus laevis oocyte assessed as ratio of GABA-mediated current in presence to absence of compound at 1 uM2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
AID51055Binding affinity to human CBG receptor (corticosteroid-binding globulins)2004Journal of medicinal chemistry, May-20, Volume: 47, Issue:11
Comparative molecular active site analysis (CoMASA). 1. An approach to rapid evaluation of 3D QSAR.
AID215949Percent inhibition against type-3 17-beta-HSD expressed in HEK293 cells at 3 uM2000Bioorganic & medicinal chemistry letters, Nov-20, Volume: 10, Issue:22
Androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase.
AID215943Inhibitory concentration against type-3 17-beta-HSD expressed in HEK293 cells2000Bioorganic & medicinal chemistry letters, Nov-20, Volume: 10, Issue:22
Androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase.
AID266559Loss of righting reflex in Xenopus laevis tadpole2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
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.
AID624606Specific activity of expressed human recombinant UGT1A12000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID382398Activity at rat GABAA alpha-1-beta-2-gamma-2L receptor expressed in Xenopus laevis expressed in assessed as ratio of current in treated to non-treated oocyte at 10 uM by electrophysiology2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID382397Activity at rat GABAA alpha-1-beta-2-gamma-2L receptor expressed in Xenopus laevis expressed in assessed as ratio of current in treated to non-treated oocyte at 1 uM by electrophysiology2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID51052In silico binding affinity to corticosteroid binding globulin (CBG)1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
Three-dimensional quantitative structure-activity relationships from molecular similarity matrices and genetic neural networks. 1. Method and validations.
AID228061Binding affinity towards human testosterone binding globulin.1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
QSAR's from similarity matrices. Technique validation and application in the comparison of different similarity evaluation methods.
AID203344Proliferative activity against Shionogi(AR+) cells at 0.1 uM concentration2002Journal of medicinal chemistry, Jan-31, Volume: 45, Issue:3
Synthesis and optimization of a new family of type 3 17 beta-hydroxysteroid dehydrogenase inhibitors by parallel liquid-phase chemistry.
AID266557Activity at rat GABA-Aalpha1 receptor plus beta-2-gamma-2L expressed in Xenopus laevis oocyte assessed as ratio of GABA-mediated current in presence to absence of compound at 10 uM2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
AID382399Activity at rat GABAA alpha-1-beta-2-gamma-2L receptor expressed in Xenopus laevis assessed as ratio of current in drug-treated to GABA-treated oocyte at 10 uM by electrophysiology2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID382393Anesthetic effect in Xenopus laevis assessed as loss of righting response at 10 uM2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID215947The ability to inhibit the Type-3 17-beta- hydroxysteroid dehydrogenase activity in transfected human embryonic kidney (HEK)-293 cells experiment 32002Journal of medicinal chemistry, Jan-31, Volume: 45, Issue:3
Synthesis and optimization of a new family of type 3 17 beta-hydroxysteroid dehydrogenase inhibitors by parallel liquid-phase chemistry.
AID212919Binding affinity towards testosterone binding globulin is expressed as log(1/k).1996Journal of medicinal chemistry, May-24, Volume: 39, Issue:11
Comparative molecular moment analysis (CoMMA): 3D-QSAR without molecular superposition.
AID266554Displacement of [35S]TBPS from GABA-A receptor in rat brain membrane2006Journal of medicinal chemistry, Jul-27, Volume: 49, Issue:15
Neurosteroid analogues. 11. Alternative ring system scaffolds: gamma-aminobutyric acid receptor modulation and anesthetic actions of benz[f]indenes.
AID51059Binding affinity to corticosteroid binding globulin1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Three-dimensional quantitative similarity-activity relationships (3D QSiAR) from SEAL similarity matrices.
AID624608Specific activity of expressed human recombinant UGT1A42000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID215945The ability to inhibit the Type-3 17-beta- hydroxysteroid dehydrogenase activity in transfected human embryonic kidney (HEK)-293 cells experiment 12002Journal of medicinal chemistry, Jan-31, Volume: 45, Issue:3
Synthesis and optimization of a new family of type 3 17 beta-hydroxysteroid dehydrogenase inhibitors by parallel liquid-phase chemistry.
AID243968Inhibition of type-3 17 beta-hydroxysteroid dehydrogenase expressed in HEK293 cells at 0.3 uM 37 degree C pH 7.42005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship.
AID624617Specific activity of expressed human recombinant UGT2B172000Annual review of pharmacology and toxicology, , Volume: 40Human UDP-glucuronosyltransferases: metabolism, expression, and disease.
AID243963Inhibition of type-3 17 beta-hydroxysteroid dehydrogenase expressed in HEK293 cells at 3 uM 37 degree C pH 7.42005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship.
AID242395Inhibition of type-3 17 beta-hydroxysteroid dehydrogenase expressed in HEK293 cells at 37 degree C pH7.4 2005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
Androsterone 3alpha-ether-3beta-substituted and androsterone 3beta-substituted derivatives as inhibitors of type 3 17beta-hydroxysteroid dehydrogenase: chemical synthesis and structure-activity relationship.
AID382391Displacement of [35S]TPBS from GABAA receptor in rat brain2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID382396Activity at rat GABAA alpha-1-beta-2-gamma-2L receptor expressed in Xenopus laevis assessed as ratio of current in treated to non-treated oocyte at 0.1 uM by electrophysiology2008European journal of medicinal chemistry, Jan, Volume: 43, Issue:1
Neurosteroid analogues. 12. Potent enhancement of GABA-mediated chloride currents at GABAA receptors by ent-androgens.
AID188186Effect on the potentiation of muscimol-stimulated 36Cl- uptake in rat brain synaptoneurosomes1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis, metabolism, and pharmacological activity of 3 alpha-hydroxy steroids which potentiate GABA-receptor-mediated chloride ion uptake in rat cerebral cortical synaptoneurosomes.
AID51058Binding affinity towards corticosteroid-binding globulin (CBG)2003Journal of medicinal chemistry, Apr-10, Volume: 46, Issue:8
Mapping property distributions of molecular surfaces: algorithm and evaluation of a novel 3D quantitative structure-activity relationship technique.
AID51049Binding affinity against corticosteroid-binding globulin1993Journal of medicinal chemistry, Feb-19, Volume: 36, Issue:4
Structure-activity relationships from molecular similarity matrices.
AID212737Binding affinity against testosterone-binding globulin (TeBG)1993Journal of medicinal chemistry, Feb-19, Volume: 36, Issue:4
Structure-activity relationships from molecular similarity matrices.
AID51056Binding affinity to the corticosteroid-binding globulin (CBG) receptor.2000Journal of medicinal chemistry, Aug-24, Volume: 43, Issue:17
GRid-INdependent descriptors (GRIND): a novel class of alignment-independent three-dimensional molecular descriptors.
AID203345Proliferative activity against Shionogi(AR+) cells at 1 uM concentration2002Journal of medicinal chemistry, Jan-31, Volume: 45, Issue:3
Synthesis and optimization of a new family of type 3 17 beta-hydroxysteroid dehydrogenase inhibitors by parallel liquid-phase chemistry.
AID977608Experimentally measured binding affinity data (IC50) for protein-ligand complexes derived from PDB1993Nature, Oct-28, Volume: 365, Issue:6449
Molecular basis of crossreactivity and the limits of antibody-antigen complementarity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,055)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990833 (78.96)18.7374
1990's57 (5.40)18.2507
2000's86 (8.15)29.6817
2010's59 (5.59)24.3611
2020's20 (1.90)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials26 (2.28%)5.53%
Reviews44 (3.86%)6.00%
Case Studies29 (2.55%)4.05%
Observational0 (0.00%)0.25%
Other1,040 (91.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research Highlights

Safety/Toxicity (8)

ArticleYear
Safety and Efficacy of Istaroxime 1.0 and 1.5 µg/kg/min for Patients With Pre-Cardiogenic Shock.
Journal of cardiac failure, Volume: 29, Issue: 7
2023
Sarcoendoplasmic reticulum Ca(2+) ATPase. A critical target in chlorine inhalation-induced cardiotoxicity.
American journal of respiratory cell and molecular biology, Volume: 52, Issue: 4
2015
Role and mechanism of subcellular Ca2+ distribution in the action of two inotropic agents with different toxicity.
Journal of molecular and cellular cardiology, Volume: 50, Issue: 5
2011
Acute heart failure with low cardiac output: can we develop a short-term inotropic agent that does not increase adverse events?
Current heart failure reports, Volume: 7, Issue: 3
2010
A phase 1-2 dose-escalating study evaluating the safety and tolerability of istaroxime and specific effects on electrocardiographic and hemodynamic parameters in patients with chronic heart failure with reduced systolic function.
The American journal of cardiology, Jan-22, Volume: 99, Issue: 2A
2007
Modulation of sarcoplasmic reticulum function by Na+/K+ pump inhibitors with different toxicity: digoxin and PST2744 [(E,Z)-3-((2-aminoethoxy)imino)androstane-6,17-dione hydrochloride].
The Journal of pharmacology and experimental therapeutics, Volume: 313, Issue: 1
2005
Diverse toxicity associated with cardiac Na+/K+ pump inhibition: evaluation of electrophysiological mechanisms.
The Journal of pharmacology and experimental therapeutics, Volume: 305, Issue: 2
2003
Protective effect of dehydroepiandrosterone against aflatoxin B1-and 7,12-dimethylbenz(a)anthracene-induced cytotoxicity and transformation in cultured cells.
Cancer research, Volume: 35, Issue: 9
1975
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Long-term Use (1)

ArticleYear
Urinary excretion of steroid metabolites after chronic androstenedione ingestion.
The Journal of clinical endocrinology and metabolism, Volume: 89, Issue: 12
2004
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pharmacokinetics (2)

ArticleYear
Gentamicin sulfate pharmacokinetics: lower levels of gentamicin in blood during fever.
The Journal of infectious diseases, Volume: 132, Issue: 3
1975
Effects of etiocholanolone-induced fever on plasma antipyrine half-lives and metabolic clearance.
Clinical pharmacology and therapeutics, Volume: 17, Issue: 4
1975
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioavailability (1)

ArticleYear
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Molecular pharmacology, Volume: 96, Issue: 5
2019
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Dosage (10)

ArticleYear
Safety and Efficacy of Istaroxime 1.0 and 1.5 µg/kg/min for Patients With Pre-Cardiogenic Shock.
Journal of cardiac failure, Volume: 29, Issue: 7
2023
Steroid profile and IRMS analysis of musk administration for doping control.
Drug testing and analysis, Volume: 9, Issue: 11-12
2017
Newer inotropes in pediatric heart failure.
Journal of cardiovascular pharmacology, Volume: 58, Issue: 2
2011
A phase 1-2 dose-escalating study evaluating the safety and tolerability of istaroxime and specific effects on electrocardiographic and hemodynamic parameters in patients with chronic heart failure with reduced systolic function.
The American journal of cardiology, Jan-22, Volume: 99, Issue: 2A
2007
Oral administration of dehydroepiandrosterone to healthy men: alteration of the urinary androgen profile and consequences for the detection of abuse in sport by gas chromatography-mass spectrometry.
Steroids, Volume: 63, Issue: 2
1998
A mechanism for the suppression of estrogen production in polycystic ovary syndrome.
The Journal of clinical endocrinology and metabolism, Volume: 81, Issue: 10
1996
Alkaline phosphatase as a marker of maturity in human neutrophils. Studies in normals dosed with aetiocholanolone and prednisolone.
Journal of clinical pathology, Volume: 33, Issue: 6
1980
Glucocorticoid-binding proteins in human acute lymphoblastic leukemic blast cells.
The Journal of clinical investigation, Volume: 52, Issue: 7
1973
Antiobesity effects of etiocholanolones in diabetes (db), viable yellow (Avy), and normal mice.
Endocrinology, Volume: 117, Issue: 6
1985
Cyproterone-mediated stimulation of delta-aminolevulinic acid synthetase in chick embryo liver cells.
Endocrinology, Volume: 99, Issue: 1
1976
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]