Page last updated: 2024-11-10

3-(1-adamantyl)-6,7,8,9-tetrahydro-5h-(1,2,4)triazolo(4,3-a)azepine

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Cross-References

ID SourceID
PubMed CID3630776
CHEMBL ID256777
SCHEMBL ID5095978
MeSH IDM0491157

Synonyms (22)

Synonym
OPREA1_175789
compound 544
CHEMBL256777 ,
merck-544
bdbm50239401
3-adamantan-1-yl-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine
3-(1-adamantyl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine
327093-42-5
AKOS015969399
SCHEMBL5095978
DTXSID40394475
SR-01000029295-1
sr-01000029295
Z55729757
merck 544
3-(adamantan-1-yl)-6,7,8,9-tetrahydro-5h-[1,2,4]triazolo[4,3-a]azepine
HMS3745K09
11ss-hsd1 inhibitor 544
EN300-16437
3-(adamantan-1-yl)-5h,6h,7h,8h,9h-[1,2,4]triazolo[4,3-a]azepine
3-[(3r,5s,7s)-adamantan-1-yl]-5h,6h,7h,8h,9h-[1,2,4]triazolo[4,3-a]azepine
EN300-27121978
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)IC50 (µMol)0.00750.00751.36125.5000AID366736
Corticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)IC50 (µMol)0.00770.00411.066710.0000AID1151397; AID1873295; AID332062; AID404225; AID466259; AID758682
17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)IC50 (µMol)3.30000.09603.94009.9000AID366737
Corticosteroid 11-beta-dehydrogenase isozyme 1Mus musculus (house mouse)IC50 (µMol)0.08500.00200.24103.7600AID1873296; AID332063; AID404226; AID466260; AID758683
Corticosteroid 11-beta-dehydrogenase isozyme 2Mus musculus (house mouse)IC50 (µMol)10.00000.08200.14400.2060AID1151400; AID332065; AID404228
Corticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)IC50 (µMol)3.25000.00040.63676.4300AID1151395; AID1873294; AID332064; AID404227
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (26)

Processvia Protein(s)Taxonomy
steroid biosynthetic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estrogen biosynthetic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
lysosome organization17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
skeletal muscle tissue development17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estrogen metabolic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
gene expression17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
bone development17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
adipose tissue development17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone biosynthetic process17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
cellular response to metal ion17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
lung developmentCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
steroid catabolic processCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
in utero embryonic development17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
placenta development17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
estrogen biosynthetic process17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
androgen metabolic process17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
response to retinoic acid17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
steroid metabolic process17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
response to hypoxiaCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
regulation of blood volume by renal aldosteroneCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
female pregnancyCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to xenobiotic stimulusCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to foodCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to insulinCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
cortisol metabolic processCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
response to glucocorticoidCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
glucocorticoid metabolic processCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (20)

Processvia Protein(s)Taxonomy
catalytic activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
steroid binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
protein binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone dehydrogenase [NAD(P)] activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
dihydrotestosterone 17-beta-dehydrogenase activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
small molecule binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
protein homodimerization activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone dehydrogenase (NAD+) activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
testosterone 17-beta-dehydrogenase (NADP+) activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
NADP binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
NADP+ binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
17-beta-hydroxysteroid dehydrogenase (NADP+) activity17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
estradiol binding17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
protein homodimerization activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
7-beta-hydroxysteroid dehydrogenase (NADP+) activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
NADP bindingCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
11-beta-hydroxysteroid dehydrogenase (NADP+) activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
cortisol dehydrogenase activityCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
steroid bindingCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
estradiol 17-beta-dehydrogenase [NAD(P)] activity17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
17-alpha,20-alpha-dihydroxypregn-4-en-3-one dehydrogenase activity17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
testosterone dehydrogenase (NAD+) activity17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
steroid bindingCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
NAD bindingCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
11-beta-hydroxysteroid dehydrogenase (NAD+) activityCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
cytoplasm17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
cytosol17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
cytosol17-beta-hydroxysteroid dehydrogenase type 1Homo sapiens (human)
endoplasmic reticulum membraneCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
membraneCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
endoplasmic reticulum membraneCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
intracellular membrane-bounded organelleCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
endoplasmic reticulum membrane17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
intracellular membrane-bounded organelle17-beta-hydroxysteroid dehydrogenase type 2Homo sapiens (human)
endoplasmic reticulum membraneCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
intracellular membrane-bounded organelleCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
intracellular membrane-bounded organelleCorticosteroid 11-beta-dehydrogenase isozyme 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
AID1151397Inhibition of human 11beta-HSD12014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID1151399Reduction in fasting blood glucose level in high fat diet-fed STZ-induced diabetes mouse model at 30 mg/kg bid for 9 days relative to vehicle-treated control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID1151402In vivo inhibition of 11beta-HSD1 in mouse assessed as inhibition of [3H]cortisone to [3H]cortisol conversion at 10 mg/kg, po measured after 4 hrs relative to control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID404230Inhibition of [3H]cortisone to [3H]cortisol conversion in mouse at 10 mg/kg, po administered as single dose after 4 hrs2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
4-Methyl-5-phenyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1151404Reduction in cumulative food intake in diet-induced obese mouse model at 20 mg/kg bid for 11 days relative to vehicle-treated control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID404227Inhibition of human 11beta HSD22008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
4-Methyl-5-phenyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1151406Reduction in postprandial blood glucose level in high fat diet-fed STZ-induced diabetes mouse model at 30 mg/kg bid for 9 days relative to vehicle-treated control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID1151401In vivo inhibition of 11beta-HSD1 in mouse assessed as inhibition of [3H]cortisone to [3H]cortisol conversion at 10 mg/kg, po measured after 1 hr relative to control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID404225Inhibition of human 11beta HSD1 by SPA assay2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
4-Methyl-5-phenyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID404228Inhibition of mouse 11beta HSD22008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
4-Methyl-5-phenyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1151407Reduction in aortic total cholesterol accumulation in high fat diet-fed mouse model at 30 mg/kg bid for 9 days relative to vehicle-treated control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID332063Inhibition of mouse 11-beta-HSD1 by SPA assay2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID332067Inhibition of 11-beta-HSD1 in mouse pharmacodynamic model assessed as inhibition of [3H]cortisone to [3H]cortisol at 10 mg/kg, po after 1 hr2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID332068Inhibition of 11-beta-HSD1 in mouse pharmacodynamic model assessed as inhibition of [3H]cortisone to [3H]cortisol at 10 mg/kg, po after 4 hrs2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID758682Inhibition of human 11beta-HSD12013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID332065Inhibition of mouse 11-beta-HSD2 by SPA assay2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1151395Inhibition of human 11beta-HSD22014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID466259Displacement of [3H]cortisone from human 11beta-HSD1 expressed in baculovirus-infected Sf9 cells after 1 hr by scintillation proximity assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Azabicyclic sulfonamides as potent 11beta-HSD1 inhibitors.
AID404229Inhibition of [3H]cortisone to [3H]cortisol conversion in mouse at 10 mg/kg, po administered as single dose after 1 hr2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
4-Methyl-5-phenyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID758683Inhibition of mouse 11beta-HSD12013European journal of medicinal chemistry, Jul, Volume: 65Discovery and structure-activity relationships of ent-Kaurene diterpenoids as potent and selective 11β-HSD1 inhibitors: potential impact in diabetes.
AID404226Inhibition of mouse 11beta HSD1 by SPA assay2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
4-Methyl-5-phenyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1873294Inhibition of human 11beta-HSD22022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Discovery of 1'-(1-phenylcyclopropane-carbonyl)-3H-spiro[isobenzofuran-1,3'-pyrrolidin]-3-one as a novel steroid mimetic scaffold for the potent and tissue-specific inhibition of 11β-HSD1 using a scaffold-hopping approach.
AID332064Inhibition of human 11-beta-HSD2 by SPA assay2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1151400Inhibition of mouse 11beta-HSD22014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID366737Inhibition of 11beta-HSD2 expressed in CHO-K1 cells assessed as conversion of [3H]cortisol to cortisone by SPA assay2008Journal of medicinal chemistry, Aug-28, Volume: 51, Issue:16
Blockade of glucocorticoid excess at the tissue level: inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 as a therapy for type 2 diabetes.
AID366736Inhibition of 11beta-HSD1 expressed in CHO-K1 cells assessed as conversion of [3H]cortisone to cortisol by SPA assay2008Journal of medicinal chemistry, Aug-28, Volume: 51, Issue:16
Blockade of glucocorticoid excess at the tissue level: inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 as a therapy for type 2 diabetes.
AID1873296Inhibition of mouse 11beta-HSD12022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Discovery of 1'-(1-phenylcyclopropane-carbonyl)-3H-spiro[isobenzofuran-1,3'-pyrrolidin]-3-one as a novel steroid mimetic scaffold for the potent and tissue-specific inhibition of 11β-HSD1 using a scaffold-hopping approach.
AID1873295Inhibition of human 11beta-HSD12022Bioorganic & medicinal chemistry letters, 08-01, Volume: 69Discovery of 1'-(1-phenylcyclopropane-carbonyl)-3H-spiro[isobenzofuran-1,3'-pyrrolidin]-3-one as a novel steroid mimetic scaffold for the potent and tissue-specific inhibition of 11β-HSD1 using a scaffold-hopping approach.
AID1151403Reduction in body weight in diet-induced obese mouse model at 20 mg/kg bid for 11 days relative to vehicle-treated control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID332062Inhibition of human 11-beta-HSD1 by SPA assay2008Bioorganic & medicinal chemistry letters, Jun-01, Volume: 18, Issue:11
Phenylcyclobutyl triazoles as selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.
AID1151405Reduction in fasting blood glucose level in diet-induced obese mouse model at 20 mg/kg bid for 11 days relative to vehicle-treated control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Medicinal chemistry of inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1).
AID466260Displacement of [3H]cortisone from mouse 11beta-HSD1 expressed in baculovirus-infected Sf9 cells after 1 hr by scintillation proximity assay2010Bioorganic & medicinal chemistry letters, Mar-01, Volume: 20, Issue:5
Azabicyclic sulfonamides as potent 11beta-HSD1 inhibitors.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (42.86)29.6817
2010's3 (42.86)24.3611
2020's1 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.47

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 Index12.47 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (85.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]