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Identification
NameMequitazine
Accession NumberDB01071  (APRD00386)
TypeSmall Molecule
GroupsApproved
DescriptionMequitazine 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
KitazeminNot Available
MetaplexanNot Available
MircolNot Available
PrimalanNot Available
ZesulanNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIY463242LY2
CAS number29216-28-2
WeightAverage: 322.467
Monoisotopic: 322.150369404
Chemical FormulaC20H22N2S
InChI KeyHOKDBMAJZXIPGC-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
IndicationFor the treatment of Hay fever, urticaria (hives) and allergic rhinitis
Structured Indications Not Available
PharmacodynamicsIn 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 actionMequitazine 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Histamine H1 receptorProteinyes
antagonist
HumanP35367 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine 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
AzaperoneAzaperone may increase the arrhythmogenic activities of Mequitazine.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
BromperidolBromperidol may increase the arrhythmogenic activities of Mequitazine.Investigational
BupropionThe serum concentration of Mequitazine can be increased when it is combined with Bupropion.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
ChloroquineThe metabolism of Mequitazine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Mequitazine.Illicit, Withdrawn
ChlorpromazineChlorpromazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
ChlorprothixeneChlorprothixene may increase the arrhythmogenic activities of Mequitazine.Approved, 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
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
DiphenhydramineThe metabolism of Mequitazine can be decreased when combined with Diphenhydramine.Approved
DolasetronDolasetron may increase the arrhythmogenic activities of Mequitazine.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
ErythromycinErythromycin may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
FencamfamineFencamfamine may increase the arrhythmogenic activities of Mequitazine.Approved, Illicit, Withdrawn
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
FluvoxamineThe metabolism of Mequitazine can be decreased when combined with Fluvoxamine.Approved, Investigational
FurazolidoneFurazolidone may increase the anticholinergic activities of Mequitazine.Approved, Vet Approved
HaloperidolHaloperidol may increase the arrhythmogenic activities of Mequitazine.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Mequitazine.Approved, Investigational
HydracarbazineHydracarbazine may increase the anticholinergic activities of Mequitazine.Approved
Hydroxyamphetamine hydrobromideHydroxyamphetamine hydrobromide 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
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
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
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
MebanazineMebanazine may increase the anticholinergic activities of Mequitazine.Withdrawn
MelperoneMelperone may increase the arrhythmogenic activities of Mequitazine.Approved
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
MethadoneMethadone may increase the arrhythmogenic activities of Mequitazine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Mequitazine.Approved, Illicit
MethotrimeprazineThe serum concentration of Mequitazine can be increased when it is combined with Methotrimeprazine.Approved
Methylene blueMethylene blue may increase the anticholinergic activities of Mequitazine.Investigational
MetoprololThe metabolism of Mequitazine can be decreased when combined with Metoprolol.Approved, Investigational
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
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
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
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
PentamidinePentamidine may increase the arrhythmogenic activities of Mequitazine.Approved
PerazinePerazine may increase the arrhythmogenic activities of Mequitazine.Investigational
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
PipotiazinePipotiazine may increase the arrhythmogenic activities of Mequitazine.Approved
PirlindolePirlindole may increase the anticholinergic activities of Mequitazine.Approved
PivhydrazinePivhydrazine may increase the anticholinergic activities of Mequitazine.Withdrawn
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
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
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, Withdrawn
SertralineThe metabolism of Mequitazine can be decreased when combined with Sertraline.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
TerbinafineThe serum concentration of Mequitazine can be increased when it is combined with Terbinafine.Approved, Investigational, Vet Approved
ThioproperazineThioproperazine may increase the arrhythmogenic activities of Mequitazine.Approved
ThioridazineThe serum concentration of Mequitazine can be increased when it is combined with Thioridazine.Approved
ThiothixeneThiothixene may increase the arrhythmogenic activities of Mequitazine.Approved
TiaprideTiapride may increase the arrhythmogenic activities of Mequitazine.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
TriflupromazineTriflupromazine may increase the arrhythmogenic activities of Mequitazine.Approved, Vet Approved
VenlafaxineThe metabolism of Mequitazine can be decreased when combined with Venlafaxine.Approved
ZiprasidoneZiprasidone may increase the arrhythmogenic activities of Mequitazine.Approved
ZotepineZotepine may increase the arrhythmogenic activities of Mequitazine.Approved
ZuclopenthixolZuclopenthixol may increase the arrhythmogenic activities of Mequitazine.Approved, Investigational
Food InteractionsNot 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
ATC CodesR06AD07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point130.5 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Quinuclidine
  • Benzenoid
  • Piperidine
  • Para-thiazine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available

Targets

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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23