Cyamemazine

Identification

Name
Cyamemazine
Accession Number
DB09000
Type
Small Molecule
Groups
Approved
Description

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).

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Tercian (Sanofi-Aventis)
Categories
UNII
A2JGV5CNU4
CAS number
3546-03-0
Weight
Average: 323.455
Monoisotopic: 323.145618377
Chemical Formula
C19H21N3S
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamineCyamemazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylamphetamine.Experimental, Illicit
3,4-MethylenedioxyamphetamineCyamemazine may decrease the stimulatory activities of 3,4-Methylenedioxyamphetamine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamineCyamemazine may decrease the stimulatory activities of 4-Bromo-2,5-dimethoxyamphetamine.Experimental, Illicit
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Cyamemazine.Approved, Investigational
AmisulprideThe risk or severity of adverse effects can be increased when Cyamemazine is combined with Amisulpride.Approved, Investigational
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Cyamemazine.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Cyamemazine.Approved
AmphetamineCyamemazine may decrease the stimulatory activities of Amphetamine.Approved, Illicit
BenzphetamineCyamemazine may decrease the stimulatory activities of Benzphetamine.Approved, Illicit
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Cyamemazine.Approved, Investigational
BuspironeThe risk or severity of adverse effects can be increased when Buspirone is combined with Cyamemazine.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Cyamemazine.Approved
ChlorphentermineCyamemazine may decrease the stimulatory activities of Chlorphentermine.Illicit, Withdrawn
CitalopramThe risk or severity of adverse effects can be increased when Citalopram is combined with Cyamemazine.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Cyamemazine.Approved, Vet Approved
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Cyamemazine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Cyamemazine.Approved
DesvenlafaxineThe risk or severity of adverse effects can be increased when Desvenlafaxine is combined with Cyamemazine.Approved
DextroamphetamineCyamemazine may decrease the stimulatory activities of Dextroamphetamine.Approved, Illicit
DextromethorphanThe risk or severity of adverse effects can be increased when Dextromethorphan is combined with Cyamemazine.Approved
DiethylpropionCyamemazine may decrease the stimulatory activities of Diethylpropion.Approved, Illicit
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Cyamemazine.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Cyamemazine.Approved
DuloxetineThe risk or severity of adverse effects can be increased when Duloxetine is combined with Cyamemazine.Approved
EletriptanThe risk or severity of adverse effects can be increased when Eletriptan is combined with Cyamemazine.Approved, Investigational
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Ergoloid mesylate is combined with Cyamemazine.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Cyamemazine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Cyamemazine.Approved
EscitalopramThe risk or severity of adverse effects can be increased when Escitalopram is combined with Cyamemazine.Approved, Investigational
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Cyamemazine.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Fluoxetine is combined with Cyamemazine.Approved, Vet Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Cyamemazine.Approved, Investigational
FrovatriptanThe risk or severity of adverse effects can be increased when Frovatriptan is combined with Cyamemazine.Approved, Investigational
GepefrineCyamemazine may decrease the stimulatory activities of Gepefrine.Experimental
HydroxyamphetamineCyamemazine may decrease the stimulatory activities of Hydroxyamphetamine.Approved
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Cyamemazine.Approved
Iofetamine I-123Cyamemazine may decrease the stimulatory activities of Iofetamine I-123.Approved
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Cyamemazine.Approved
LevomilnacipranThe risk or severity of adverse effects can be increased when Levomilnacipran is combined with Cyamemazine.Approved
LinezolidThe risk or severity of adverse effects can be increased when Linezolid is combined with Cyamemazine.Approved, Investigational
LisdexamfetamineCyamemazine may decrease the stimulatory activities of Lisdexamfetamine.Approved, Investigational
LithiumLithium may increase the neurotoxic activities of Cyamemazine.Approved
LorcaserinThe risk or severity of adverse effects can be increased when Lorcaserin is combined with Cyamemazine.Approved
MaprotilineThe risk or severity of adverse effects can be increased when Maprotiline is combined with Cyamemazine.Approved
MephedroneCyamemazine may decrease the stimulatory activities of Mephedrone.Investigational
MephentermineCyamemazine may decrease the stimulatory activities of Mephentermine.Approved
MequitazineCyamemazine may increase the arrhythmogenic activities of Mequitazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Cyamemazine.Approved
MethamphetamineCyamemazine may decrease the stimulatory activities of Methamphetamine.Approved, Illicit
MethoxyphenamineCyamemazine may decrease the stimulatory activities of Methoxyphenamine.Experimental
MethylphenidateThe risk or severity of adverse effects can be increased when Cyamemazine is combined with Methylphenidate.Approved, Investigational
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Cyamemazine.Approved, Investigational
MetyrosineThe risk or severity of adverse effects can be increased when Metyrosine is combined with Cyamemazine.Approved
MidomafetamineCyamemazine may decrease the stimulatory activities of Midomafetamine.Experimental, Illicit, Investigational
MilnacipranThe risk or severity of adverse effects can be increased when Milnacipran is combined with Cyamemazine.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Cyamemazine.Approved
MMDACyamemazine may decrease the stimulatory activities of MMDA.Experimental, Illicit
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Cyamemazine.Approved
NaratriptanThe risk or severity of adverse effects can be increased when Naratriptan is combined with Cyamemazine.Approved, Investigational
NefazodoneThe risk or severity of adverse effects can be increased when Nefazodone is combined with Cyamemazine.Approved, Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Cyamemazine.Approved
ParoxetineThe risk or severity of adverse effects can be increased when Paroxetine is combined with Cyamemazine.Approved, Investigational
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Cyamemazine.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Cyamemazine.Approved
PhentermineCyamemazine may decrease the stimulatory activities of Phentermine.Approved, Illicit
Porfimer sodiumCyamemazine may increase the photosensitizing activities of Porfimer sodium.Approved, Investigational
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Cyamemazine.Approved
PromethazineThe risk or severity of adverse effects can be increased when Promethazine is combined with Cyamemazine.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Cyamemazine.Approved
PseudoephedrineCyamemazine may decrease the stimulatory activities of Pseudoephedrine.Approved
QuinagolideThe therapeutic efficacy of Quinagolide can be decreased when used in combination with Cyamemazine.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Cyamemazine.Approved
RitobegronCyamemazine may decrease the stimulatory activities of Ritobegron.Investigational
RizatriptanThe risk or severity of adverse effects can be increased when Rizatriptan is combined with Cyamemazine.Approved
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Cyamemazine.Approved, Investigational, Vet Approved
SertralineThe risk or severity of adverse effects can be increased when Sertraline is combined with Cyamemazine.Approved
SulpirideThe risk or severity of adverse effects can be increased when Cyamemazine is combined with Sulpiride.Approved, Investigational
SumatriptanThe risk or severity of adverse effects can be increased when Sumatriptan is combined with Cyamemazine.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Cyamemazine.Approved
Tedizolid PhosphateThe risk or severity of adverse effects can be increased when Tedizolid Phosphate is combined with Cyamemazine.Approved
TetrabenazineThe risk or severity of adverse effects can be increased when Tetrabenazine is combined with Cyamemazine.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Cyamemazine.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Cyamemazine.Approved
TrazodoneThe risk or severity of adverse effects can be increased when Trazodone is combined with Cyamemazine.Approved, Investigational
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Cyamemazine.Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Cyamemazine.Approved
VenlafaxineThe risk or severity of adverse effects can be increased when Venlafaxine is combined with Cyamemazine.Approved
VerteporfinCyamemazine may increase the photosensitizing activities of Verteporfin.Approved, Investigational
VilazodoneThe risk or severity of adverse effects can be increased when Vilazodone is combined with Cyamemazine.Approved
VortioxetineThe risk or severity of adverse effects can be increased when Vortioxetine is combined with Cyamemazine.Approved
YohimbineThe therapeutic efficacy of Cyamemazine can be decreased when used in combination with Yohimbine.Approved, Vet Approved
ZolmitriptanThe risk or severity of adverse effects can be increased when Zolmitriptan is combined with Cyamemazine.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 2,877,224.

General References
Not Available
External Links
KEGG Drug
D07307
PubChem Compound
62865
PubChem Substance
310264961
ChemSpider
56597
BindingDB
86057
ChEBI
135379
ChEMBL
CHEMBL2104153
Drugs.com
Drugs.com Drug Page
Wikipedia
Cyamemazine
ATC Codes
N05AA06 — Cyamemazine

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
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-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 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
Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Tertiary aliphatic/aromatic amine / Para-thiazine / Benzenoid / Tertiary amine / Tertiary aliphatic amine / Carbonitrile
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on June 17, 2014 10:28 / Updated on December 01, 2017 16:11