Identification

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Name
Deramciclane
Accession Number
DB06512
Type
Small Molecule
Groups
Investigational
Description

Deramciclane (EGIS-3886) is used for the treatment of a number of anxiety disorders. Deramciclane differs from other anti anxiety medications in that it is not a benzodiazepine and so has a different structure and target. It antagonizes 5-HT2A receptors, agonizes 5-HT2C receptors, and functions as a GABA reuptake inhibitor.

Structure
Thumb
Synonyms
Not Available
External IDs
EGIS-3886 / EGYT 3886 / EGYT-3886 / EGYT3886
Categories
UNII
O5KFK61E74
CAS number
120444-71-5
Weight
Average: 301.474
Monoisotopic: 301.240564622
Chemical Formula
C20H31NO
InChI Key
QOBGWWQAMAPULA-RLLQIKCJSA-N
InChI
InChI=1S/C20H31NO/c1-18(2)17-11-12-19(18,3)20(15-17,22-14-13-21(4)5)16-9-7-6-8-10-16/h6-10,17H,11-15H2,1-5H3/t17-,19-,20+/m1/s1
IUPAC Name
dimethyl(2-{[(1R,2S,4R)-1,7,7-trimethyl-2-phenylbicyclo[2.2.1]heptan-2-yl]oxy}ethyl)amine
SMILES
[H][C@]12CC[C@](C)(C1(C)C)[C@@](C2)(OCCN(C)C)C1=CC=CC=C1

Pharmacology

Indication

Investigated for use/treatment in anxiety disorders.

Pharmacodynamics
Not Available
Mechanism of action

Deramciclane is a new putative non-benzodiazepine-type anxiolytic compound. It is a selective serotonin 5-HT(2A) and 5-HT(2C) receptor antagonist and has also inverse agonist properties.

TargetActionsOrganism
U5-hydroxytryptamine receptor 2A
antagonist
Humans
U5-hydroxytryptamine receptor 2C
inverse agonist
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Deramciclane is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Deramciclane is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Deramciclane is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineDeramciclane may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Deramciclane.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Deramciclane is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Deramciclane.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Deramciclane is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineDeramciclane may increase the excretion rate of 6-O-benzylguanine which could result in a lower serum level and potentially a reduction in efficacy.
7-DeazaguanineDeramciclane may increase the excretion rate of 7-Deazaguanine which could result in a lower serum level and potentially a reduction in efficacy.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Kovacs I, Maksay G, Simonyi M: Inhibition of high-affinity synaptosomal uptake of gamma-aminobutyric acid by a bicyclo-heptane derivative. Arzneimittelforschung. 1989 Mar;39(3):295-7. [PubMed:2502985]
External Links
PubChem Compound
119590
PubChem Substance
347827775
ChemSpider
106785
ChEMBL
CHEMBL2104698
Wikipedia
Deramciclane

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00103 mg/mLALOGPS
logP5.22ALOGPS
logP4.3ChemAxon
logS-5.5ALOGPS
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity92.59 m3·mol-1ChemAxon
Polarizability36.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Bicyclic monoterpenoids
Alternative Parents
Aromatic monoterpenoids / Benzylethers / Trialkylamines / Dialkyl ethers / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aromatic monoterpenoid / Bornane monoterpenoid / Bicyclic monoterpenoid / Benzylether / Monocyclic benzene moiety / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Ether / Dialkyl ether
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Kanerva H, Vilkman H, Nagren K, Kilkku O, Kuoppamaki M, Syvalahti E, Hietala J: Brain 5-HT2A receptor occupancy of deramciclane in humans after a single oral administration--a positron emission tomography study. Psychopharmacology (Berl). 1999 Jul;145(1):76-81. [PubMed:10445375]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inverse agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Palvimaki EP, Majasuo H, Kuoppamaki M, Mannisto PT, Syvalahti E, Hietala J: Deramciclane, a putative anxiolytic drug, is a serotonin 5-HT2C receptor inverse agonist but fails to induce 5-HT2C receptor down-regulation. Psychopharmacology (Berl). 1998 Mar;136(2):99-104. [PubMed:9551765]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Laine K, De Bruyn S, Bjorklund H, Rouru J, Hanninen J, Scheinin H, Anttila M: Effect of the novel anxiolytic drug deramciclane on cytochrome P(450) 2D6 activity as measured by desipramine pharmacokinetics. Eur J Clin Pharmacol. 2004 Feb;59(12):893-8. Epub 2004 Jan 17. [PubMed:14730412]

Drug created on March 19, 2008 10:35 / Updated on December 02, 2019 07:24