Deramciclane
Identification
- Generic Name
- Deramciclane
- DrugBank Accession Number
- DB06512
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Deramciclane (DB06512)
- Weight
- Average: 301.474
Monoisotopic: 301.240564622 - Chemical Formula
- C20H31NO
- Synonyms
- Deramciclane
- External IDs
- EGIS-3886
- EGYT 3886
- EGYT-3886
- EGYT3886
Pharmacology
- Indication
Investigated for use/treatment in anxiety disorders.
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Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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.
Target Actions Organism U5-hydroxytryptamine receptor 2A antagonistHumans U5-hydroxytryptamine receptor 2C inverse agonistHumans - 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
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Deramciclane is combined with 1,2-Benzodiazepine. Acebutolol The metabolism of Acebutolol can be decreased when combined with Deramciclane. Acenocoumarol The risk or severity of adverse effects can be increased when Deramciclane is combined with Acenocoumarol. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Deramciclane. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Deramciclane. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Deramciclane. Aclidinium Deramciclane may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Deramciclane is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Deramciclane. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Deramciclane. 
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- Not Available
Categories
- Drug Categories
- Anti-Anxiety Agents
- Anticonvulsants
- Antidepressive Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (weak)
- Cytochrome P-450 Enzyme Inhibitors
- Monoterpenes
- Neurotransmitter Agents
- Norbornanes
- Psychotropic Drugs
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Terpenes
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- Amine / Aromatic homopolycyclic compound / Aromatic monoterpenoid / Benzenoid / Benzylether / Bicyclic monoterpenoid / Bornane monoterpenoid / Dialkyl ether / Ether / Hydrocarbon derivative
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- O5KFK61E74
- CAS number
- 120444-71-5
- 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
References
- General References
- 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. [Article]
- External Links
- PubChem Compound
- 119590
- PubChem Substance
- 347827775
- ChemSpider
- 106785
- ChEMBL
- CHEMBL2104698
- ZINC
- ZINC000003643198
- Wikipedia
- Deramciclane
Clinical Trials
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
Property Value Source Water Solubility 0.00103 mg/mL ALOGPS logP 5.22 ALOGPS logP 4.3 ChemAxon logS -5.5 ALOGPS pKa (Strongest Basic) 8.87 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 12.47 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 92.59 m3·mol-1 ChemAxon Polarizability 36.46 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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. [Article]
- 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
- 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. [Article]
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
- 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. [Article]
Drug created on March 19, 2008 16:35 / Updated on February 21, 2021 18:52