Page last updated: 2024-12-09

1-adamantyl(piperidino)methanone

1-Adamantyl(piperidino)methanone, also known as **N-piperidin-1-yl-1-adamantanecarboxamide**, is a chemical compound with the formula C16H25NO. It is a white crystalline solid, soluble in organic solvents.

Here's why it's important for research:

**1. Pharmacological Activity:**

* **Anti-inflammatory properties:** Studies have shown that 1-adamantyl(piperidino)methanone exhibits significant anti-inflammatory effects, possibly by inhibiting the production of pro-inflammatory cytokines like TNF-α.
* **Analgesic effects:** This compound has been shown to possess analgesic properties, potentially acting as a potent inhibitor of pain pathways.
* **Neuroprotective effects:** Some research suggests that 1-adamantyl(piperidino)methanone could protect neurons from damage, offering potential therapeutic applications in neurological disorders.

**2. Chemical Structure:**

* **Unique scaffold:** The combination of the adamantane core and the piperidine ring provides a rigid and stable structure, which can be modified to create various derivatives with different pharmacological activities.
* **Versatility:** The compound can be used as a starting material for synthesizing novel drug candidates with enhanced potency and selectivity.

**3. Research Applications:**

* **Drug discovery:** Scientists are actively exploring the potential of 1-adamantyl(piperidino)methanone and its derivatives as promising drug candidates for treating inflammation, pain, and neurological diseases.
* **Structure-activity relationship (SAR) studies:** Researchers utilize this compound to understand how structural modifications affect its biological activity, leading to the development of more effective and targeted drugs.
* **Mechanistic investigations:** Studies are underway to elucidate the precise molecular mechanisms by which this compound exerts its pharmacological effects.

**Overall, 1-adamantyl(piperidino)methanone holds significant promise as a lead compound for drug development in several therapeutic areas. Its unique chemical structure, combined with its promising pharmacological activity, makes it a valuable tool for research and drug discovery.**

**Please note:** This information is for educational purposes only and should not be taken as medical advice. It is important to consult with qualified healthcare professionals for any medical concerns or before making decisions related to your health or treatment.

Cross-References

ID SourceID
PubMed CID584509
CHEMBL ID245590
CHEBI ID183758
SCHEMBL ID3457055
SCHEMBL ID19841773

Synonyms (35)

Synonym
smr000117086
MLS000526612
OPREA1_290126
adamantan-1-yl-piperidin-1-yl-methanone
MAYBRIDGE1_008125
SR-01000396865-2
OPREA1_633750
STK125639
piperidin-1-yl(tricyclo[3.3.1.1~3,7~]dec-1-yl)methanone
CHEMBL245590 ,
HMS564J07
AKOS000612261
bdbm50207772
1-adamantyl(piperidin-1-yl)methanone
CHEBI:183758
1-adamantyl(piperidino)methanone
adamantanyl piperidyl ketone
HMS2178P18
CCG-55067
F0020-1641
(3r,5r,7r)-adamantan-1-yl(piperidin-1-yl)methanone
22508-49-2
AH-357/03517015
1-(1-adamantylcarbonyl)piperidine
SCHEMBL3457055
1-(1-adamantylcarbonyl)piperidine #
BURUIZXRHQWZQI-UHFFFAOYSA-N
tricyclo[3,3,1,1(3,7)]decane, 1-piperidylcarbonyl-
1-(adamantane-1-carbonyl)piperidine
Z54082320
SR-01000396865-1
sr-01000396865
SCHEMBL19841773
BRD-K73970226-001-07-4
EN300-15027076
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylpiperidine
[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]

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.01580.003245.467312,589.2998AID2517
glp-1 receptor, partialHomo sapiens (human)Potency28.18380.01846.806014.1254AID624417
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency39.81070.035520.977089.1251AID504332
[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)
Corticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)IC50 (µMol)0.19300.00411.066710.0000AID306869
Corticosteroid 11-beta-dehydrogenase isozyme 1Mus musculus (house mouse)IC50 (µMol)0.13400.00200.24103.7600AID306871
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (2)

Processvia Protein(s)Taxonomy
lung developmentCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
steroid catabolic processCorticosteroid 11-beta-dehydrogenase isozyme 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
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.
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.
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
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID306869Inhibition of human 11beta-HSD1 expressed in HEK293 cells after 2 hrs by scintillation proximity assay2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Discovery and biological evaluation of adamantyl amide 11beta-HSD1 inhibitors.
AID306870Inhibition of human 11beta-HSD2 at 10 uM by scintillation proximity assay2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Discovery and biological evaluation of adamantyl amide 11beta-HSD1 inhibitors.
AID306871Inhibition of mouse 11beta-HSD1 expressed in CHO cells after 4 hrs by scintillation proximity assay2007Bioorganic & medicinal chemistry letters, May-15, Volume: 17, Issue:10
Discovery and biological evaluation of adamantyl amide 11beta-HSD1 inhibitors.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (22.22)29.6817
2010's5 (55.56)24.3611
2020's2 (22.22)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.04

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 Index12.04 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.34 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.04)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
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