Mequitazine
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| Trade names | Primalan |
| AHFS/Drugs.com | International Drug Names |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.045.005 |
| Chemical and physical data | |
| Formula | C20H22N2S |
| Molar mass | 322.47g·mol−1 |
| 3D model (JSmol) | |
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Mequitazine(trade namePrimalan) is anH1antagonistandanticholinergicof thephenothiazinechemical class.It is used to treatallergiesandrhinitis.
It was patented in 1969 and came into medical use in 1976.[2]
Contraindications[edit]
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.
Adverse reactions[edit]
CNS depression including slightdrowsinessto deep sleep, lassitude,dizziness,incoordination.Headache,psychomotor impairmentandantimuscariniceffects. Rarely,rashesandhypersensitivity reactions,blood disorders,convulsions,sweating,myalgia,paraesthesias,extrapyramidal effects,tremor,confusion,sleep and GI disturbances,tinnitus,hypotension,hair loss.Photosensitivity,jaundice.
Drug interactions[edit]
Enhances effects of CNS depressants e.g.alcohol,barbiturates,hypnotics,opioid analgesics,anxiolyticsandantipsychotics.Can mask signs ofototoxicitycaused byaminoglycosides.QTprolongation (which can lead totorsades de pointesarrhythmia) reported withspiramycin.
Synthesis[edit]
Same precursor as forQuifenadine.Note that the synthesis has changed over the years from the original. One route seems to involve aJohnson–Corey–Chaykovsky reactionof the starting ketone, although another secondary route is also discussed.
References[edit]
- ^"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.John Wiley & Sons. p. 548.ISBN9783527607495.
- ^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.PMID19881287.
- ^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.PMID21657243.
Further reading[edit]
- 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.PMID16568706.
- 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.PMID14987305.S2CID23019669.
- 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.PMID9454781.
- 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.PMID9188930.S2CID34785561.
External links[edit]
- "Mequitazine".Drug Information Portal.U.S. National Library of Medicine.
