Cyamemazine

Identification

Generic Name
Cyamemazine
DrugBank Accession Number
DB09000
Background

Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class used primarily in the treatment of schizophrenia and psychosis-associated anxiety. Cyamemazine actually behaves like an atypical antipsychotic, due to its potent anxiolytic effects (5-HT2C) and lack of extrapyramidal side effects (5-HT2A).

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 323.455
Monoisotopic: 323.145618377
Chemical Formula
C19H21N3S
Synonyms
  • Cyamemazine

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Cyamemazine is combined with 1,2-Benzodiazepine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Cyamemazine.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Cyamemazine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Cyamemazine.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Cyamemazine.
Food Interactions
Not Available

Products

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International/Other Brands
Tercian (Sanofi-Aventis)

Categories

ATC Codes
N05AA06 — Cyamemazine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Phenothiazines
Direct Parent
Phenothiazines
Alternative Parents
Alkyldiarylamines / Diarylthioethers / Benzenoids / 1,4-thiazines / Trialkylamines / Nitriles / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyldiarylamine / Amine / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Benzenoid / Carbonitrile / Diarylthioether / Hydrocarbon derivative / Nitrile
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
A2JGV5CNU4
CAS number
3546-03-0
InChI Key
SLFGIOIONGJGRT-UHFFFAOYSA-N
InChI
InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3
IUPAC Name
10-[3-(dimethylamino)-2-methylpropyl]-10H-phenothiazine-2-carbonitrile
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2SC2=C1C=C(C=C2)C#N

References

Synthesis Reference

U.S. Patent 2,877,224.

General References
Not Available
KEGG Drug
D07307
PubChem Compound
62865
PubChem Substance
310264961
ChemSpider
56597
BindingDB
86057
RxNav
21877
ChEBI
135379
ChEMBL
CHEMBL2104153
Drugs.com
Drugs.com Drug Page
Wikipedia
Cyamemazine

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)204-205U.S. Patent 2,877,224.
Predicted Properties
PropertyValueSource
Water Solubility0.029 mg/mLALOGPS
logP4.28ALOGPS
logP4.27Chemaxon
logS-4ALOGPS
pKa (Strongest Basic)9.42Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area30.27 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity99.09 m3·mol-1Chemaxon
Polarizability36.48 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-MSsplash10-052r-4091000000-8fd4f49543d5acc4171d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fk9-0809000000-e9a47ba9e9b612c317f0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0029000000-688c415606fcea11bb52
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0029000000-bace050610190a6af660
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0q29-9355000000-66285b2e31caa1879c98
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dr-0190000000-0d53fef3947fb7c85f1c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-5290000000-0730f877de6790187b95
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-167.3835
predicted
DeepCCS 1.0 (2019)
[M+H]+169.7415
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.07875
predicted
DeepCCS 1.0 (2019)

Drug created at June 17, 2014 16:28 / Updated at February 21, 2021 18:52