Chemical compound
Pharmaceutical compound
Mequitazine (trade namePrimalan ) is anH1 antagonist andanticholinergic of thephenothiazine chemical class . It is used to treatallergies andrhinitis .
It was patented in 1969 and came into medical use in 1976.[ 2]
Severe liver disease; premature infants or full-term neonates.
Special precautions [ edit ] Pregnancy ,lactation ; severe cardiovascular disorders;asthma ; angle-closureglaucoma ,urinary retention ,prostatic hyperplasia ,pyloroduodenal obstruction ; renal and hepatic impairment; elderly, children;epilepsy . May impair ability to drive or operate machinery.
CNS depression including slightdrowsiness to deep sleep, lassitude,dizziness ,incoordination .Headache ,psychomotor impairment andantimuscarinic effects. Rarely,rashes andhypersensitivity reactions , blood disorders,convulsions ,sweating ,myalgia ,paraesthesias ,extrapyramidal effects ,tremor ,confusion , sleep and GI disturbances,tinnitus ,hypotension ,hair loss .Photosensitivity ,jaundice .
Enhances effects of CNS depressants e.g.alcohol ,barbiturates ,hypnotics ,opioid analgesics ,anxiolytics andantipsychotics . Can mask signs ofototoxicity caused byaminoglycosides .QT prolongation (which can lead totorsades de pointes arrhythmia) reported withspiramycin .
Same precursor as forQuifenadine . Note that the synthesis has changed over the years from the original. One route seems to involve aJohnson–Corey–Chaykovsky reaction of the starting ketone, although another secondary route is also discussed.
Thieme Prec:[ 3] [ 4] [ 5] [ 6] ^ "Active substance: mequitazine" (PDF) .List of nationally authorised medicinal products . Amsterdam: European Medicines Agency. 15 October 2020.^ Fischer J, Ganellin CR (2006).Analogue-based Drug Discovery ISBN 9783527607495 ^ US 4546185 , Bondiou JC, Hodac F, Legroux D, issued Pharmuka Laboratoires ^ Gonnot V, Nicolas M, Mioskowski C, Baati R (November 2009)."Expedient synthesis of mequitazine an antihistaminic drug by palladium catalyzed allylic alkylation of sodium phenothiazinate" .Chemical & Pharmaceutical Bulletin .57 (11):1300– 2.doi :10.1248/cpb.57.1300 PMID 19881287 . ^ Guminski Y, Fabre V, Lesimple P, Imbert T (June 1999). "An efficient synthesis of mequitazine".Organic Preparations and Procedures International .31 (3):319– 323.doi :10.1080/00304949909458326 . ^ Leroux S, Larquetoux L, Nicolas M, Doris E (July 2011). "Asymmetric synthesis of (+)-mequitazine from quinine".Organic Letters .13 (13):3549– 51.doi :10.1021/ol2012567 .PMID 21657243 . Ramírez Chanona N, del Rio Navarro BE, Pérez Martín J (November–December 2005). "[Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience]".Revista Alergia Mexico (in Spanish).52 (6):221– 225.PMID 16568706 . Theunissen EL, Vermeeren A, van Oers AC, van Maris I, Ramaekers JG (February 2004). "A dose-ranging study of the effects of mequitazine on actual driving, memory and psychomotor performance as compared to dexchlorpheniramine, cetirizine and placebo".Clinical and Experimental Allergy .34 (2):250– 258.doi :10.1111/j.1365-2222.2004.01874.x .PMID 14987305 .S2CID 23019669 . Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, et al. (February 1998)."Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes" (PDF) .The Journal of Pharmacology and Experimental Therapeutics .284 (2):437– 442.PMID 9454781 . Persi L, Dupin O, Arnaud B, Trinquand C, Michel FB, Bousquet J (April 1997). "Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis".Allergy .52 (4):451– 454.doi :10.1111/j.1398-9995.1997.tb01028.x .PMID 9188930 .S2CID 34785561 .
H1
Agonists Antagonists Others: Atypical antipsychotics (e.g.,aripiprazole ,asenapine ,brexpiprazole ,brilaroxazine ,clozapine ,iloperidone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,ziprasidone ,zotepine )Phenylpiperazine antidepressants (e.g.,hydroxynefazodone ,nefazodone ,trazodone ,triazoledione )Tetracyclic antidepressants (e.g.,amoxapine ,loxapine ,maprotiline ,mianserin ,mirtazapine ,oxaprotiline )Tricyclic antidepressants (e.g.,amitriptyline ,butriptyline ,clomipramine ,desipramine ,dosulepin (dothiepin) ,doxepin ,imipramine ,iprindole ,lofepramine ,nortriptyline ,protriptyline ,trimipramine )Typical antipsychotics (e.g.,chlorpromazine ,flupenthixol ,fluphenazine ,loxapine ,perphenazine ,prochlorperazine ,thioridazine ,thiothixene )
H2
H3
H4
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g.,brompheniramine ,buclizine ,captodiame ,chlorphenamine (chlorpheniramine) ,cinnarizine ,clemastine ,cyproheptadine ,dimenhydrinate ,dimetindene ,diphenhydramine ,doxylamine ,meclizine ,mequitazine ,perlapine ,phenindamine ,pheniramine ,phenyltoloxamine ,promethazine ,propiomazine ,triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g.,clozapine ,fluperlapine ,olanzapine (+fluoxetine ),rilapine ,quetiapine ,tenilapine ,zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol ,+indacaterol ,+neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,femoxetine ,paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g.,amitriptyline (+perphenazine ),amitriptylinoxide ,butriptyline ,cidoxepin ,clomipramine ,desipramine ,desmethyldesipramine ,dibenzepin ,dosulepin (dothiepin) ,doxepin ,imipramine ,lofepramine ,nitroxazepine ,northiaden (desmethyldosulepin) ,nortriptyline ,protriptyline ,quinupramine ,trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Tropine benzilate Trospium chloride Typical antipsychotics (e.g.,chlorpromazine ,chlorprothixene ,cyamemazine (cyamepromazine) ,loxapine ,mesoridazine ,thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (andprodrugs )
N
Y (what is this?) (verify)
