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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:10 UTC
HMDB IDHMDB0015204
Secondary Accession Numbers
  • HMDB15204
Metabolite Identification
Common NameMequitazine
DescriptionMequitazine, also known as kitazemin or mircol, 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. Mequitazine is a drug which is used for the treatment of hay fever, urticaria (hives) and allergic rhinitis. Mequitazine is a very strong basic compound (based on its pKa). In humans, mequitazine is involved in mequitazine h1-antihistamine action. Headache, psychomotor impairment and antimuscarinic effects. Enhances effects of CNS depressants e.g. alcohol, barbiturates, hypnotics, opioid analgesics, anxiolytics and antipsychotics. CNS depression including slight drowsiness to deep sleep, lassitude, dizziness, incoordination. Pregnancy, lactation; severe cardiovascular disorders; asthma; angle-closure glaucoma, urinary retention, prostatic hyperplasia, pyloroduodenal obstruction; renal and hepatic impairment; elderly, children; epilepsy. Rarely, rashes and hypersensitivity reactions, blood disorders, convulsions, sweating, myalgia, paraesthesias, extrapyramidal effects, tremor, confusion, sleep and GI disturbances, tinnitus, hypotension, hair loss. QT prolongation (which can lead to torsades de pointes arrhythmia) reported with spiramycin. Can mask signs of ototoxicity caused by aminoglycosides. Mequitazine (trade name Primalan) is an H1 antagonist and anticholinergic of the phenothiazine chemical class. It was patented in 1969 and came into medical use in 1976. It is used to treat allergies and rhinitis. Severe liver disease; premature infants or full-term neonates. May impair ability to drive or operate machinery.
Structure
Data?1582753270
Synonyms
ValueSource
KitazeminKegg
Mequitazine hydrochlorideHMDB
3-Methylquinuclidinyl-10-phenothiazineHMDB
MircolHMDB
Mequitazine tartrate, (R-(r*,r*))-isomerHMDB
PrimalanHMDB
QuitadrillHMDB
Chemical FormulaC20H22N2S
Average Molecular Weight322.467
Monoisotopic Molecular Weight322.150369404
IUPAC Name10-{1-azabicyclo[2.2.2]octan-3-ylmethyl}-10H-phenothiazine
Traditional Namemequitazine
CAS Registry Number29216-28-2
SMILES
C(C1CN2CCC1CC2)N1C2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
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
InChI KeyHOKDBMAJZXIPGC-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Aryl thioether
  • Quinuclidine
  • Tertiary aliphatic/aromatic amine
  • Piperidine
  • Para-thiazine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Thioether
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.004 g/LNot Available
LogP4.7Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP5.38ALOGPS
logP4.19ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)8.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.05 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available172.74431661259
DarkChem[M-H]-PredictedNot Available170.56231661259

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-1792000000-f3d460bef0cf903cf8102017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0229-3984000000-3ce274e900b70e58cb372017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0229-3984000000-3ce274e900b70e58cb372017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0409000000-67b79e76ee71f682ee1c2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0902000000-e17e677434bd389f60452016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-fa7f5c70f1d14d13235b2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0109000000-bbd40c8f9af776ed7e802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03k9-0494000000-6d797cc31cfccb88916e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0900000000-c2249f8b238ba5566b1f2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01071 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01071 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01071
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3926
KEGG Compound IDC12755
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMequitazine
METLIN IDNot Available
PubChem Compound4066
PDB IDNot Available
ChEBI ID212175
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]

Enzymes

General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase 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
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
55783.6
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 ]