Identification

Name
Mequitazine
Accession Number
DB01071  (APRD00386)
Type
Small Molecule
Groups
Approved
Description

Mequitazine is a histamine H1 antagonist (antihistamine). It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

Structure
Thumb
Synonyms
  • Kitazemin
  • Mequitazina
  • Mequitazinum
International/Other Brands
Kitazemin / Metaplexan / Mircol / Primalan / Zesulan
Categories
UNII
Y463242LY2
CAS number
29216-28-2
Weight
Average: 322.467
Monoisotopic: 322.150369404
Chemical Formula
C20H22N2S
InChI Key
HOKDBMAJZXIPGC-UHFFFAOYSA-N
InChI
InChI=1S/C20H22N2S/c1-3-7-19-17(5-1)22(18-6-2-4-8-20(18)23-19)14-16-13-21-11-9-15(16)10-12-21/h1-8,15-16H,9-14H2
IUPAC Name
10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine
SMILES
C(C1CN2CCC1CC2)N1C2=CC=CC=C2SC2=CC=CC=C12

Pharmacology

Indication

For the treatment of Hay fever, urticaria (hives) and allergic rhinitis

Structured Indications
Not Available
Pharmacodynamics

In allergic reactions an allergen interacts with and cross-links surface IgE antibodies on mast cells and basophils. Once the mast cell-antibody-antigen complex is formed, a complex series of events occurs that eventually leads to cell-degranulation and the release of histamine (and other chemical mediators) from the mast cell or basophil. Once released, histamine can react with local or widespread tissues through histamine receptors. Histamine, acting on H1-receptors, produces pruritis, vasodilatation, hypotension, flushing, headache, tachycardia, and bronchoconstriction. Histamine also increases vascular permeability and potentiates pain. Mequitazine is a histamine H1 antagonist. It competes with histamine for the normal H1-receptor sites on effector cells of the gastrointestinal tract, blood vessels and respiratory tract. It provides effective, temporary relief of sneezing, watery and itchy eyes, and runny nose due to hay fever and other upper respiratory allergies.

Mechanism of action

Mequitazine binds to the histamine H1 receptor sites on effector cells in the gastrointestinal tract, blood vessels, and respiratory tract. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
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
PathwayCategory
Mequitazine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Mequitazine.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Mequitazine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Mequitazine.Experimental, Illicit
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the anticholinergic activities of Mequitazine.Experimental
AbirateroneThe serum concentration of Mequitazine can be increased when it is combined with Abiraterone.Approved
AcepromazineAcepromazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
AceprometazineAceprometazine may increase the arrhythmogenic activities of Mequitazine.Approved
AcetophenazineAcetophenazine may increase the arrhythmogenic activities of Mequitazine.Approved
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Mequitazine resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
AmiodaroneThe serum concentration of Mequitazine can be increased when it is combined with Amiodarone.Approved, Investigational
AmisulprideAmisulpride may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
AmperozideAmperozide may increase the arrhythmogenic activities of Mequitazine.Experimental
AmphetamineAmphetamine may decrease the sedative activities of Mequitazine.Approved, Illicit
AripiprazoleAripiprazole may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
ArtemetherThe metabolism of Mequitazine can be decreased when combined with Artemether.Approved
AsenapineAsenapine may increase the arrhythmogenic activities of Mequitazine.Approved
AtomoxetineThe metabolism of Mequitazine can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Mequitazine is combined with Atorvastatin.Approved
AzaperoneAzaperone may increase the arrhythmogenic activities of Mequitazine.Investigational, Vet Approved
BenmoxinBenmoxin may increase the anticholinergic activities of Mequitazine.Withdrawn
BenperidolBenperidol may increase the arrhythmogenic activities of Mequitazine.Investigational
BenzphetamineBenzphetamine may decrease the sedative activities of Mequitazine.Approved, Illicit
Benzylpenicilloyl PolylysineMequitazine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Mequitazine.Approved
BetaxololThe metabolism of Mequitazine can be decreased when combined with Betaxolol.Approved
BifeprunoxBifeprunox may increase the arrhythmogenic activities of Mequitazine.Investigational
BrexpiprazoleBrexpiprazole may increase the arrhythmogenic activities of Mequitazine.Approved
BrofaromineBrofaromine may increase the anticholinergic activities of Mequitazine.Experimental
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Mequitazine.Approved, Investigational
BromperidolBromperidol may increase the arrhythmogenic activities of Mequitazine.Investigational
BupropionThe serum concentration of Mequitazine can be increased when it is combined with Bupropion.Approved
ButaperazineButaperazine may increase the arrhythmogenic activities of Mequitazine.Experimental
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Mequitazine.Approved
CariprazineCariprazine may increase the arrhythmogenic activities of Mequitazine.Approved
CaroxazoneCaroxazone may increase the anticholinergic activities of Mequitazine.Withdrawn
CelecoxibThe metabolism of Mequitazine can be decreased when combined with Celecoxib.Approved, Investigational
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Mequitazine.Withdrawn
ChloroquineThe metabolism of Mequitazine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Mequitazine.Illicit, Withdrawn
ChlorproethazineChlorproethazine may increase the arrhythmogenic activities of Mequitazine.Experimental
ChlorpromazineChlorpromazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
ChlorprothixeneChlorprothixene may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational, Withdrawn
CholecalciferolThe metabolism of Mequitazine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe metabolism of Mequitazine can be decreased when combined with Cimetidine.Approved
CinacalcetThe serum concentration of Mequitazine can be increased when it is combined with Cinacalcet.Approved
CitalopramThe metabolism of Mequitazine can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Mequitazine can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Mequitazine can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Mequitazine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopenthixolClopenthixol may increase the arrhythmogenic activities of Mequitazine.Experimental
ClothiapineClothiapine may increase the arrhythmogenic activities of Mequitazine.Experimental
ClotrimazoleThe metabolism of Mequitazine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineClozapine may increase the arrhythmogenic activities of Mequitazine.Approved
CobicistatThe serum concentration of Mequitazine can be increased when it is combined with Cobicistat.Approved
CocaineThe serum concentration of Mequitazine can be increased when it is combined with Cocaine.Approved, Illicit
CyamemazineCyamemazine may increase the arrhythmogenic activities of Mequitazine.Approved
DapiprazoleDapiprazole may increase the arrhythmogenic activities of Mequitazine.Approved
DarifenacinThe metabolism of Mequitazine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Mequitazine can be increased when it is combined with Darunavir.Approved
DelavirdineThe serum concentration of Mequitazine can be increased when it is combined with Delavirdine.Approved
DesipramineThe metabolism of Mequitazine can be decreased when combined with Desipramine.Approved
DextroamphetamineDextroamphetamine may decrease the sedative activities of Mequitazine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Mequitazine.Approved, Illicit
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Mequitazine.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Mequitazine.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Mequitazine.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Mequitazine.Approved
DiphenhydramineThe metabolism of Mequitazine can be decreased when combined with Diphenhydramine.Approved
DixyrazineDixyrazine may increase the arrhythmogenic activities of Mequitazine.Experimental
DolasetronDolasetron may increase the arrhythmogenic activities of Mequitazine.Approved
DosulepinThe serum concentration of Mequitazine can be increased when it is combined with Dosulepin.Approved
DronedaroneThe metabolism of Mequitazine can be decreased when combined with Dronedarone.Approved
DroperidolDroperidol may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
DuloxetineThe metabolism of Mequitazine can be decreased when combined with Duloxetine.Approved
EcopipamEcopipam may increase the arrhythmogenic activities of Mequitazine.Investigational
EliglustatThe metabolism of Mequitazine can be decreased when combined with Eliglustat.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Mequitazine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Mequitazine.Approved
ErythromycinErythromycin may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
FencamfamineFencamfamine may increase the arrhythmogenic activities of Mequitazine.Approved, Illicit, Withdrawn
FluanisoneFluanisone may increase the arrhythmogenic activities of Mequitazine.Experimental
FluoxetineThe serum concentration of Mequitazine can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolFlupentixol may increase the arrhythmogenic activities of Mequitazine.Approved, Withdrawn
FluphenazineFluphenazine may increase the arrhythmogenic activities of Mequitazine.Approved
FluspirileneFluspirilene may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Mequitazine.Approved
FluvoxamineThe metabolism of Mequitazine can be decreased when combined with Fluvoxamine.Approved, Investigational
FurazolidoneFurazolidone may increase the anticholinergic activities of Mequitazine.Approved, Investigational, Vet Approved
GepefrineGepefrine may decrease the sedative activities of Mequitazine.Experimental
HaloperidolHaloperidol may increase the arrhythmogenic activities of Mequitazine.Approved
HarmalineHarmaline may increase the anticholinergic activities of Mequitazine.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Mequitazine.Approved, Investigational
HydracarbazineHydracarbazine may increase the anticholinergic activities of Mequitazine.Experimental
HydroxyamphetamineHydroxyamphetamine may decrease the sedative activities of Mequitazine.Approved
IloperidoneIloperidone may increase the arrhythmogenic activities of Mequitazine.Approved
ImipramineThe metabolism of Mequitazine can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Mequitazine can be decreased when combined with Indinavir.Approved
Iofetamine I-123Iofetamine I-123 may decrease the sedative activities of Mequitazine.Approved
IproclozideIproclozide may increase the anticholinergic activities of Mequitazine.Withdrawn
IproniazidIproniazid may increase the anticholinergic activities of Mequitazine.Withdrawn
IsocarboxazidIsocarboxazid may increase the anticholinergic activities of Mequitazine.Approved
IsoniazidThe metabolism of Mequitazine can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Mequitazine can be decreased when combined with Ketoconazole.Approved, Investigational
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Mequitazine.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Mequitazine.Approved, Investigational
LithiumLithium may increase the arrhythmogenic activities of Mequitazine.Approved
LopinavirThe serum concentration of Mequitazine can be increased when it is combined with Lopinavir.Approved
LorcaserinThe metabolism of Mequitazine can be decreased when combined with Lorcaserin.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Mequitazine.Approved, Investigational
LoxapineLoxapine may increase the arrhythmogenic activities of Mequitazine.Approved
LumefantrineThe metabolism of Mequitazine can be decreased when combined with Lumefantrine.Approved
LurasidoneLurasidone may increase the arrhythmogenic activities of Mequitazine.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Mequitazine.Illicit, Investigational, Withdrawn
ManidipineThe metabolism of Mequitazine can be decreased when combined with Manidipine.Approved, Investigational
MebanazineMebanazine may increase the anticholinergic activities of Mequitazine.Withdrawn
MelperoneMelperone may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Mequitazine.Investigational
MephentermineMephentermine may decrease the sedative activities of Mequitazine.Approved
MesoridazineMesoridazine may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Mequitazine.Experimental
MethadoneMethadone may increase the arrhythmogenic activities of Mequitazine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Mequitazine.Approved, Illicit
MethotrimeprazineMethotrimeprazine may increase the arrhythmogenic activities of Mequitazine.Approved
MethoxyphenamineMethoxyphenamine may decrease the sedative activities of Mequitazine.Experimental
Methylene blueMethylene blue may increase the anticholinergic activities of Mequitazine.Approved, Investigational
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Mequitazine.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Mequitazine.Approved
MetoprololThe metabolism of Mequitazine can be decreased when combined with Metoprolol.Approved, Investigational
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Mequitazine.Experimental
Midomafetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Mequitazine.Experimental, Illicit, Investigational
MidostaurinThe serum concentration of Mequitazine can be increased when it is combined with Midostaurin.Approved
MinaprineMinaprine may increase the anticholinergic activities of Mequitazine.Approved
MirabegronThe metabolism of Mequitazine can be decreased when combined with Mirabegron.Approved
MMDAMMDA may decrease the sedative activities of Mequitazine.Experimental, Illicit
MoclobemideMoclobemide may increase the anticholinergic activities of Mequitazine.Approved
MolindoneMolindone may increase the arrhythmogenic activities of Mequitazine.Approved
MoperoneMoperone may increase the arrhythmogenic activities of Mequitazine.Experimental
MosapramineMosapramine may increase the arrhythmogenic activities of Mequitazine.Experimental
MoxifloxacinMoxifloxacin may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
NevirapineThe metabolism of Mequitazine can be decreased when combined with Nevirapine.Approved
NialamideNialamide may increase the anticholinergic activities of Mequitazine.Withdrawn
NicardipineThe metabolism of Mequitazine can be decreased when combined with Nicardipine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Mequitazine.Approved, Investigational
NilotinibThe metabolism of Mequitazine can be decreased when combined with Nilotinib.Approved, Investigational
OctamoxinOctamoxin may increase the anticholinergic activities of Mequitazine.Withdrawn
OlanzapineOlanzapine may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
OndansetronOndansetron may increase the arrhythmogenic activities of Mequitazine.Approved
OsanetantOsanetant may increase the arrhythmogenic activities of Mequitazine.Investigational
OxypertineOxypertine may increase the arrhythmogenic activities of Mequitazine.Experimental
PaliperidonePaliperidone may increase the arrhythmogenic activities of Mequitazine.Approved
PanobinostatThe serum concentration of Mequitazine can be increased when it is combined with Panobinostat.Approved, Investigational
PargylinePargyline may increase the anticholinergic activities of Mequitazine.Approved
ParoxetineThe serum concentration of Mequitazine can be increased when it is combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Mequitazine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PenfluridolPenfluridol may increase the arrhythmogenic activities of Mequitazine.Experimental
PentamidinePentamidine may increase the arrhythmogenic activities of Mequitazine.Approved
PerazinePerazine may increase the arrhythmogenic activities of Mequitazine.Investigational
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Mequitazine.Approved, Investigational, Vet Approved, Withdrawn
PerospironePerospirone may increase the arrhythmogenic activities of Mequitazine.Approved
PerphenazinePerphenazine may increase the arrhythmogenic activities of Mequitazine.Approved
PhenelzinePhenelzine may increase the anticholinergic activities of Mequitazine.Approved
PheniprazinePheniprazine may increase the anticholinergic activities of Mequitazine.Withdrawn
PhenoxypropazinePhenoxypropazine may increase the anticholinergic activities of Mequitazine.Withdrawn
PhenterminePhentermine may decrease the sedative activities of Mequitazine.Approved, Illicit
PimozidePimozide may increase the arrhythmogenic activities of Mequitazine.Approved
PipamperonePipamperone may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
PipotiazinePipotiazine may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
PirlindolePirlindole may increase the anticholinergic activities of Mequitazine.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Mequitazine.Approved
PivhydrazinePivhydrazine may increase the anticholinergic activities of Mequitazine.Withdrawn
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Mequitazine.Approved
ProchlorperazineProchlorperazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
PromazinePromazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
PropericiazinePropericiazine may increase the arrhythmogenic activities of Mequitazine.Approved
ProthipendylProthipendyl may increase the arrhythmogenic activities of Mequitazine.Investigational
PseudoephedrinePseudoephedrine may decrease the sedative activities of Mequitazine.Approved
QuetiapineQuetiapine may increase the arrhythmogenic activities of Mequitazine.Approved
QuinidineThe serum concentration of Mequitazine can be increased when it is combined with Quinidine.Approved
QuinineThe metabolism of Mequitazine can be decreased when combined with Quinine.Approved
RacloprideRaclopride may increase the arrhythmogenic activities of Mequitazine.Investigational
RanolazineThe metabolism of Mequitazine can be decreased when combined with Ranolazine.Approved, Investigational
RasagilineRasagiline may increase the anticholinergic activities of Mequitazine.Approved
RemoxiprideRemoxipride may increase the arrhythmogenic activities of Mequitazine.Approved, Withdrawn
ReserpineReserpine may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
RisperidoneRisperidone may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
RitanserinRitanserin may increase the arrhythmogenic activities of Mequitazine.Investigational
RitobegronRitobegron may decrease the sedative activities of Mequitazine.Investigational
RitonavirThe serum concentration of Mequitazine can be increased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Mequitazine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Mequitazine can be decreased when combined with Ropinirole.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Mequitazine.Approved
SafrazineSafrazine may increase the anticholinergic activities of Mequitazine.Withdrawn
SelegilineSelegiline may increase the anticholinergic activities of Mequitazine.Approved, Investigational, Vet Approved
SertindoleSertindole may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational, Withdrawn
SertralineThe metabolism of Mequitazine can be decreased when combined with Sertraline.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Mequitazine.Approved
StiripentolThe serum concentration of Mequitazine can be increased when it is combined with Stiripentol.Approved
SulpirideSulpiride may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
SultoprideSultopride may increase the arrhythmogenic activities of Mequitazine.Experimental
TerbinafineThe serum concentration of Mequitazine can be increased when it is combined with Terbinafine.Approved, Investigational, Vet Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Mequitazine.Experimental
TetrahydropalmatineTetrahydropalmatine may increase the arrhythmogenic activities of Mequitazine.Investigational
ThiopropazateThiopropazate may increase the arrhythmogenic activities of Mequitazine.Experimental
ThioproperazineThioproperazine may increase the arrhythmogenic activities of Mequitazine.Approved
ThioridazineThioridazine may increase the arrhythmogenic activities of Mequitazine.Approved, Withdrawn
ThiothixeneThiothixene may increase the arrhythmogenic activities of Mequitazine.Approved
TiaprideTiapride may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
TiclopidineThe metabolism of Mequitazine can be decreased when combined with Ticlopidine.Approved
TipranavirThe serum concentration of Mequitazine can be increased when it is combined with Tipranavir.Approved, Investigational
ToloxatoneToloxatone may increase the anticholinergic activities of Mequitazine.Approved
Trans-2-PhenylcyclopropylamineTrans-2-Phenylcyclopropylamine may increase the anticholinergic activities of Mequitazine.Experimental
TranylcypromineTranylcypromine may increase the anticholinergic activities of Mequitazine.Approved
TrifluoperazineTrifluoperazine may increase the arrhythmogenic activities of Mequitazine.Approved
TrifluperidolTrifluperidol may increase the arrhythmogenic activities of Mequitazine.Experimental
TriflupromazineTriflupromazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Mequitazine.Approved, Experimental
VenlafaxineThe metabolism of Mequitazine can be decreased when combined with Venlafaxine.Approved
VeraliprideVeralipride may increase the arrhythmogenic activities of Mequitazine.Experimental
ZiprasidoneZiprasidone may increase the arrhythmogenic activities of Mequitazine.Approved
ZotepineZotepine may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
ZuclopenthixolZuclopenthixol may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Charles Mioskowski, Vanessa Gonnot, Rachid Baati, Marc Nicolas, "NOVEL QUINUCLIDINE DERIVATIVE USEFUL IN THE PREPARATION OF MEQUITAZINE." U.S. Patent US20100105897, issued April 29, 2010.

US20100105897
General References
  1. Ramirez Chanona N, del Rio Navarro BE, Perez Martin J: [Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience]. Rev Alerg Mex. 2005 Nov-Dec;52(6):221-5. [PubMed:16568706]
  2. Theunissen EL, Vermeeren A, van Oers AC, van Maris I, Ramaekers JG: A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo. Clin Exp Allergy. 2004 Feb;34(2):250-8. [PubMed:14987305]
  3. Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T: Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. J Pharmacol Exp Ther. 1998 Feb;284(2):437-42. [PubMed:9454781]
  4. Persi L, Dupin O, Arnaud B, Trinquand C, Michel FB, Bousquet J: Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis. Allergy. 1997 Apr;52(4):451-4. [PubMed:9188930]
External Links
Human Metabolome Database
HMDB15204
KEGG Drug
D01324
KEGG Compound
C12755
PubChem Compound
4066
PubChem Substance
46505779
ChemSpider
3926
ChEBI
31821
ChEMBL
CHEMBL73451
Therapeutic Targets Database
DAP001078
PharmGKB
PA164748010
Wikipedia
Mequitazine
ATC Codes
R06AD07 — Mequitazine

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)130.5 °CPhysProp
logP4.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00401 mg/mLALOGPS
logP5.38ALOGPS
logP4.19ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)8.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.05 m3·mol-1ChemAxon
Polarizability36.25 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9717
Blood Brain Barrier+0.9916
Caco-2 permeable+0.6548
P-glycoprotein substrateSubstrate0.6645
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IIInhibitor0.8319
Renal organic cation transporterInhibitor0.771
CYP450 2C9 substrateNon-substrate0.7951
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.7094
CYP450 1A2 substrateNon-inhibitor0.8592
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8941
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8928
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9016
Ames testNon AMES toxic0.8458
CarcinogenicityNon-carcinogens0.9536
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.0874 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8568
hERG inhibition (predictor II)Inhibitor0.7754
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0229-3984000000-3ce274e900b70e58cb37

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 / Quinuclidines / Piperidines / Benzenoids / 1,4-thiazines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenothiazine / Alkyldiarylamine / Diarylthioether / Aryl thioether / Quinuclidine / Tertiary aliphatic/aromatic amine / Piperidine / Para-thiazine / Benzenoid / Tertiary aliphatic amine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
phenothiazines (CHEBI:31821)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T: Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes. J Pharmacol Exp Ther. 1998 Feb;284(2):437-42. [PubMed:9454781]
  2. ter Laak AM, Venhorst J, Donne-Op den Kelder GM, Timmerman H: The histamine H1-receptor antagonist binding site. A stereoselective pharmacophoric model based upon (semi-)rigid H1-antagonists and including a known interaction site on the receptor. J Med Chem. 1995 Aug 18;38(17):3351-60. [PubMed:7650688]
  3. Wiseman LR, Faulds D: Ebastine. a review of its pharmacological properties and clinical efficacy in the treatment of allergic disorders. Drugs. 1996 Feb;51(2):260-77. [PubMed:8808167]
  4. Yakuo I, Ishii K, Seto Y, Imano K, Takeyama K, Nakamura H, Karasawa T: [Pharmacological study of ebastine, a novel histamine H1-receptor antagonist]. Nihon Yakurigaku Zasshi. 1994 Mar;103(3):121-35. [PubMed:7511558]
  5. Wang YJ, Yu CF, Chen LC, Chen CH, Lin JK, Liang YC, Lin CH, Lin SY, Chen CF, Ho YS: Ketoconazole potentiates terfenadine-induced apoptosis in human Hep G2 cells through inhibition of cytochrome p450 3A4 activity. J Cell Biochem. 2002;87(2):147-59. [PubMed:12244568]
  6. Nicholson AN, Stone BM: The H1-antagonist mequitazine: studies on performance and visual function. Eur J Clin Pharmacol. 1983;25(4):563-6. [PubMed:6418550]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:46