Details of the Drug

General Information of Drug (ID: DMAFBCY)

Drug Name
Mequitazine
Synonyms
Butix; Instotal; Kitazemin; Mequitazina; Mequitazinum; Metaplexan; Mircol; Primalan; Quitadrill; Vigigan; Virginan; Zesulan; Italfarmaco brand of mequitazine; Mequitazina [Spanish]; Mequitazine hydrochloride; Pierre Fabre brand of mequitazine; LM 209; Kitazemin (TN); LM-209; Mequitazina [INN-Spanish]; Mequitazinum [INN-Latin]; Mequitazine (JP15/INN); Mequitazine [INN:BAN:DCF:JAN]; Mequitazine tartrate, (R-(R*,R*))-isomer; 10-(1-Azabicyclo[2.2.2]oct-3-ylmethyl)-10H-phenothiazine; 10-(1-azabicyclo(2.2.2)oct-8-ylmethyl)phenothiazine; 10-(1-azabicyclo[2.2.2]octan-3-ylmethyl)phenothiazine; 10-(3-Quinuclidinylmethyl)phenothiazine; 10H-Phenothiazine, 10-(1-azabicyclo(2.2.2)oct-3-ylmethyl)-(9CI); 3-Methylquinuclidinyl-10-phenothiazine
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Respiratory disease CB40 Phase 2 [2]
Therapeutic Class
Antihistamines
Affected Organisms
Humans and other mammals
ATC Code
R06AD07: Mequitazine
R06AD: Phenothiazine derivatives
R06A: ANTIHISTAMINES FOR SYSTEMIC USE
R06: ANTIHISTAMINES FOR SYSTEMIC USE
R: RESPIRATORY SYSTEM
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 322.5
Logarithm of the Partition Coefficient (xlogp) 4.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 3
Chemical Identifiers
Formula
C20H22N2S
IUPAC Name
10-(1-azabicyclo[2.2.2]octan-3-ylmethyl)phenothiazine
Canonical SMILES
C1CN2CCC1C(C2)CN3C4=CC=CC=C4SC5=CC=CC=C53
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
InChIKey
HOKDBMAJZXIPGC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4066
ChEBI ID
CHEMBL31821
CAS Number
29216-28-2
UNII
Y463242LY2
DrugBank ID
DB01071
TTD ID
D09IMS
VARIDT ID
DR01379
INTEDE ID
DR1030
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine H1 receptor (H1R) TTTIBOJ HRH1_HUMAN Antagonist [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2D6 (CYP2D6)
Main DME 		DECB0K3 CP2D6_HUMAN Substrate [5]
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Molecular Expression Atlas of This Drug

The Studied Disease Allergic rhinitis
ICD Disease Classification CA08.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Histamine H1 receptor (H1R) DTT HRH1 6.74E-01 0.13 0.43
P-glycoprotein 1 (ABCB1) DTP P-GP 6.54E-01 1.95E-01 4.04E-01
Cytochrome P450 2D6 (CYP2D6) DME CYP2D6 8.70E-01 2.98E-02 1.22E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drug information of Mequitazine, 2008. eduDrugs.
2 ClinicalTrials.gov (NCT01951222) Bronchodilator Properties and Safety in Asthma. U.S. National Institutes of Health.
3 Efficiency of mequitazine in the treatment of allergic rhinitis and chronic urticaria in children. A bibliographic systematic review. Rev Alerg Mex. 2008 Jan-Feb;55(1):3-9.
4 Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37.
5 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.