Page last updated: 2024-12-07

deramciclane

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

Description

deramciclane: structure in first source; RN refers to (exo-EGYT 3886)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID119590
CHEMBL ID2104698
SCHEMBL ID548911
MeSH IDM0168213

Synonyms (27)

Synonym
egyt 3886
n,n-dimethyl-2-(((1r,2s,4r)-2-phenyl-2-bornyl)oxy)ethylamine
deramciclane
deramciclane [inn]
ethanamine, n,n-dimethyl-2-((1,7,7-trimethyl-2-phenylbicyclo(2.2.1)hept-2-yl)oxy)-, (1r-exo)-
ethanamine, n,n-dimethyl-2-(((1r,2s,4r)-1,7,7-trimethyl-2-phenylbicyclo(2.2.1)hept-2-yl)oxy)-
unii-o5kfk61e74
120444-71-5
o5kfk61e74 ,
CHEMBL2104698
deramciclane [who-dd]
deramciclane [mi]
egyt3886
n,n-dimethyl-2-[[(1r,4r,6s)-1,7,7-trimethyl-6-phenyl-6-bicyclo[2.2.1]heptanyl]oxy]ethanamine
gtpl5490
SCHEMBL548911
QOBGWWQAMAPULA-RLLQIKCJSA-N
AKOS024259070
DTXSID10152862
HY-101630
CS-6595
DB06512
n,n-dimethyl-2-(((1r,2s,4r)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]heptan-2-yl)oxy)ethanamine
Q5261335
n,n-dimethyl-2-[[(1r,2s,4r)-1,7,7-trimethyl-2-phenyl-2-bicyclo[2.2.1]heptanyl]oxy]ethanamine
A898662
MS-24348

Research Excerpts

Overview

Deramciclane (EGIS-3886) is a novel anxiolytic agent that binds with high affinity to 5-HT2A/2C receptors. It appears to be a safe and well-tolerated drug.

ExcerptReferenceRelevance
"Deramciclane is a new compound that has shown anxiolytic effects in animal experiments and in human studies. "( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
2.09
"Deramciclane appears to be a safe and well-tolerated drug and we suggest that it might be useful in the treatment of anxiety in alcoholics."( Comparison of deramciclane to benzodiazepine agonists in behavioural activity of mice and in alcohol drinking of alcohol-preferring rats.
Honkanen, A; Ingman, K; Korpi, ER; Sallinen, J, 2004
)
1.41
"Deramciclane (EGIS-3886) is a novel anxiolytic agent that binds with high affinity to 5-HT2A/2C receptors. "( Deramciclane, a putative anxiolytic drug, is a serotonin 5-HT2C receptor inverse agonist but fails to induce 5-HT2C receptor down-regulation.
Hietala, J; Kuoppamäki, M; Majasuo, H; Männistö, PT; Pälvimäki, EP; Syvälahti, E, 1998
)
3.19
"Deramciclane fumarate is a new 5-HT2A and 5-HT2C receptor antagonist with putative anxiolytic effects. "( Brain 5-HT2A receptor occupancy of deramciclane in humans after a single oral administration--a positron emission tomography study.
Hietala, J; Kanerva, H; Kilkku, O; Kuoppamäki, M; Någren, K; Syvälahti, E; Vilkman, H, 1999
)
2.02
"Deramciclane is a new putative non-benzodiazepine-type anxiolytic compound. "( Pharmacokinetics and safety of deramciclane during multiple oral dosing.
Drabant, S; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Urtti, A, 1999
)
2.03

Actions

ExcerptReferenceRelevance
"Deramciclane does not inhibit CYP3A4 activity as measured by buspirone pharmacokinetics, and there were no indications of relevant pharmacodynamic interaction after multiple doses of deramciclane and a single dose of buspirone."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
2.04

Treatment

ExcerptReferenceRelevance
"Deramciclane treatment resulted in 5-HT2A receptor occupancy of up to 78%, but no significant effect of chronic treatment on 5-HT2A receptor agonist binding levels was found."( Deramciclane, a putative anxiolytic drug, is a serotonin 5-HT2C receptor inverse agonist but fails to induce 5-HT2C receptor down-regulation.
Hietala, J; Kuoppamäki, M; Majasuo, H; Männistö, PT; Pälvimäki, EP; Syvälahti, E, 1998
)
2.46

Toxicity

ExcerptReferenceRelevance
" Tolerability was assessed by monitoring safety laboratory variables, electrocardiogram, heart rate, blood pressure and adverse events."( Pharmacokinetics and safety of deramciclane during multiple oral dosing.
Drabant, S; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Urtti, A, 1999
)
0.59
" Only few adverse events were reported, all mild and transient in nature."( Pharmacokinetics and safety of deramciclane during multiple oral dosing.
Drabant, S; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Urtti, A, 1999
)
0.59

Pharmacokinetics

Pharmacodynamic testing and measurement of plasma prolactin concentrations were carried out on day 7 and day 8 to assess the pharmacodynamic consequences of deramciclane and buspirone co-administration. The elimination phase half-life of the parent compound is similar after intravenous and oral administration.

ExcerptReferenceRelevance
" The pharmacokinetic parameters were calculated for a single dose and after repeated administration."( Pharmacokinetics and safety of deramciclane during multiple oral dosing.
Drabant, S; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Urtti, A, 1999
)
0.59
" The mean elimination half-life of deramciclane for 10, 30 and 60 mg doses prolonged from 24."( Pharmacokinetics and safety of deramciclane during multiple oral dosing.
Drabant, S; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Urtti, A, 1999
)
0.87
"The pharmacokinetic properties of deramciclane fumarate (EGIS-3886), a new potential anxiolitic agent, and its N-desmethyl metabolite have been investigated in Wistar rats after 10 mgkg(-1) deramciclane fumarate was administered orally, intraperitoneally or intravenously."( Oral, intraperitoneal and intravenous pharmacokinetics of deramciclane and its N-desmethyl metabolite in the rat.
Abermann, M; Al-Behaisi, S; Bojti, E; Grézal, G; Klebovich, I; Nemes, KB, 2000
)
0.83
" The elimination half-life increased from about 20 h to about 32 h with the increasing dose."( The single dose pharmacokinetics and safety of deramciclane in healthy male volunteers.
Drabant, S; Heinonen, E; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Tarpila, S; Urtti, A, 1999
)
0.56
" The secondary objective was to study the possible pharmacodynamic interaction between these two anxiolytic drugs."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.59
" Pharmacodynamic testing and measurement of plasma prolactin concentrations were carried out on day 7 and day 8 to assess the pharmacodynamic consequences of deramciclane and buspirone co-administration."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.79
"001) and 20% increase in the elimination half-life ( P=0."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
0.59
"Deramciclane does not inhibit CYP3A4 activity as measured by buspirone pharmacokinetics, and there were no indications of relevant pharmacodynamic interaction after multiple doses of deramciclane and a single dose of buspirone."( Effect of the novel anxiolytic drug deramciclane on the pharmacokinetics and pharmacodynamics of the CYP3A4 probe drug buspirone.
Ahokoski, O; Anttila, M; Björklund, H; Hänninen, J; Huupponen, R; Laine, K; Palovaara, S; Rouru, J; Ruuskanen, J, 2003
)
2.04
" The aim of this study was to determine the pharmacokinetic parameters of deramciclane after intravenous and oral administration, and its oral bioavailability."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.87
" Oral bioavailability of deramciclane and the pharmacokinetic parameters of deramciclane and N-desmethylderamciclane, the principal metabolite, were determined after intravenous and oral administration of the parent drug."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.95
"50h, respectively, and the half-life of the elimination phase was 26."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.64
" The elimination phase half-life of the parent compound is similar after intravenous and oral administration, whereas the apparent half-life of N-desmethylderamciclane is longer after intravenous than after oral administration of the parent compound."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.84
" Measurement of secretion of saliva, Visual Analogue Scale assessment of dryness of mouth and tiredness were carried out on day 7 and day 8 to assess the pharmacodynamic consequences of deramciclane or paroxetine co-administration with desipramine."( Effect of the novel anxiolytic drug deramciclane on cytochrome P(450) 2D6 activity as measured by desipramine pharmacokinetics.
Anttila, M; Björklund, H; De Bruyn, S; Hänninen, J; Laine, K; Rouru, J; Scheinin, H, 2004
)
0.79
" The mean apparent elimination half-life of deramciclane was 24."( Pharmacokinetics of deramciclane and N-desmethylderamciclane after single and repeated oral doses in healthy volunteers.
Anttila, M; Huupponen, R; Kanerva, H; Miettinen, T; Rouru, J; Scheinin, M, 2004
)
0.91

Compound-Compound Interactions

ExcerptReferenceRelevance
"Overpressured layer chromatography was combined with the highly sensitive and rapid digital autoradiography (DAR) and mass spectrometry to separate, detect, and identify 3H- and 14C-labeled deramciclane metabolites in different biological matrixes."( Application of overpressured layer chromatography combined with digital autoradiography and mass spectrometry in the study of deramciclane metabolism.
Karancsi, T; Klebovich, I; Ludányi, K; Mincsovics, E; Nemes, KB; Szúnyog, J; Ujszászy, K; Vékey, K,
)
0.53

Bioavailability

The oral bioavailability of deramciclane is large and uniform enough to allow its clinical use as tablets.

ExcerptReferenceRelevance
" Due to a moderate first-pass metabolism the absolute bioavailability was only 45-61%."( Pharmacokinetics of deramciclane in dogs after single oral and intravenous dosing and multiple oral dosing.
Alhonen-Raatesalmi, A; Huuskonen, H; Kanerva, H; Nevalainen, T; Urtti, A, 1998
)
0.62
" Oral bioavailability of deramciclane and the pharmacokinetic parameters of deramciclane and N-desmethylderamciclane, the principal metabolite, were determined after intravenous and oral administration of the parent drug."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.95
" The mean oral bioavailability of deramciclane was 44% (range 27-58%) and 36% (23-50%) after administration of the oral solution and tablet, respectively."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.92
" The oral bioavailability of deramciclane is large and uniform enough to allow its clinical use as tablets."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.93
"The effect of a high-fat meal on the oral bioavailability of deramciclane 30 mg tablet was evaluated in 18 healthy male volunteers in a randomised, single dose, two-way crossover study."( Influence of food on the oral bioavailability of deramciclane from film-coated tablet in healthy male volunteers.
Al-Behaisi, S; Anttila, M; Drabant, S; Gachályi, B; Grézal, G; Horvai, G; Horváth, V; Kanerva, H; Klebovich, I; Nemes, KB; Tolokán, A, 2004
)
0.82

Dosage Studied

Deramciclane had no effect on alcohol consumption in either acute or repeated dosing study.

ExcerptRelevanceReference
" The aim of this study was to reveal the pharmacokinetics and tolerability of deramciclane during repeated oral dosing in healthy male volunteers."( Pharmacokinetics and safety of deramciclane during multiple oral dosing.
Drabant, S; Helminen, A; Huupponen, R; Kanerva, H; Kilkku, O; Klebovich, I; Rouru, J; Scheinin, M; Urtti, A, 1999
)
0.82
"9h after intravenous and about 25 h after oral dosing of the parent compound."( Pharmacokinetics of deramciclane, a novel anxiolytic agent, after intravenous and oral administration.
Anttila, M; Björklund, H; Huupponen, R; Paija, O; Rouru, J; Salonen, M, 2003
)
0.64
" Deramciclane had no effect on alcohol consumption in either acute or repeated dosing study."( Comparison of deramciclane to benzodiazepine agonists in behavioural activity of mice and in alcohol drinking of alcohol-preferring rats.
Honkanen, A; Ingman, K; Korpi, ER; Sallinen, J, 2004
)
1.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID781326pKa (acid-base dissociation constant) as determined by Avdeef ref: DOI: 10.1002/047145026X2014Pharmaceutical research, Apr, Volume: 31, Issue:4
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (2.63)18.7374
1990's15 (39.47)18.2507
2000's18 (47.37)29.6817
2010's4 (10.53)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: 29.06

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 Index29.06 (24.57)
Research Supply Index3.93 (2.92)
Research Growth Index5.80 (4.65)
Search Engine Demand Index34.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (29.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (25.00%)5.53%
Reviews2 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other28 (70.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]