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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/05/26 20:53:02」(JST)

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Mequitazine (trade name Primalan) is an antihistamine and anticholinergic of the phenothiazine chemical class. It is used to treat allergies and rhinitis.

Contraindications

Severe liver disease; premature infants or full-term neonates .

Special precautions

Pregnancy, lactation; severe CardioVascular disorders; asthma; angle-closure glaucoma, urinary retention, prostatic hyperplasia, pyloroduodenal obstruction; renal and hepatic impairment; elderly, children; epilepsy. May impair ability to drive or operate machinery.

Adverse drug reactions

CNS depression including slight drowsiness to deep sleep, lassitude, dizziness, incoordination. Headache, psychomotor impairment and antimuscarinic effects. Rarely, rashes and hypersensitivity reactions, blood disorders, convulsions, sweating, myalgia, paraesthesias, extrapyramidal effects, tremor, confusion, sleep and GI disturbances, tinnitus, hypotension, hair loss. Photosensitivity, jaundice.

Drug Interactions

Enhanced effects of CNS depressants e.g. alcohol, barbiturates, hypnotics, opioid analgesics, anxiolytic sedatives and antipsychotics. Can mask signs of ototoxicity caused by aminoglycosides. QT prolongation reported with spiramycin.

References

Ramírez Chanona N, del Rio Navarro B, Pérez Martín J (2005). "Efficacy of mequitazine (Primalan) on the relief of symptoms of allergic rhinoconjunctivitis in children. Documented clinical experience". Rev Alerg Mex 52 (6): 221–5. PMID 16568706.
Theunissen E, Vermeeren A, van Oers A, van Maris I, Ramaekers J (2004). "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 34 (2): 250–8. doi:10.1111/j.1365-2222.2004.01874.x. PMID 14987305.
Nakamura K, Yokoi T, Kodama T, Inoue K, Nagashima K, Shimada N, Shimizu T, Kamataki T (1998). "Oxidation of histamine H1 antagonist mequitazine is catalyzed by cytochrome P450 2D6 in human liver microsomes.". J Pharmacol Exp Ther 284 (2): 437–42. PMID 9454781.
Persi L, Dupin O, Arnaud B, Trinquand C, Michel F, Bousquet J (1997). "Efficacy of mequitazine in comparison with placebo assessed by ocular challenge with allergen in allergic conjunctivitis.". Allergy 52 (4): 451–4. doi:10.1111/j.1398-9995.1997.tb01028.x. PMID 9188930.

English Journal

Asymmetric synthesis of (+)-mequitazine from quinine.

Leroux S, Larquetoux L, Nicolas M, Doris E.SourceCEA, iBiTecS, Service de Chimie Bioorganique et de Marquage, 91191 Gif-sur-Yvette, France.
Organic letters.Org Lett.2011 Jul 1;13(13):3549-51. Epub 2011 Jun 9.
The first asymmetric synthesis of the antihistaminic drug mequitazine is reported. Our approach started from quinine, a Cinchona alkaloid, whose chiral information was exploited for setting up the stereogenic center of (+)-mequitazine.
PMID 21657243

Expedient synthesis of mequitazine an antihistaminic drug by palladium catalyzed allylic alkylation of sodium phenothiazinate.

Gonnot V, Nicolas M, Mioskowski C, Baati R.SourceFaculty of Pharmacy, University of Strasbourg, CNRS-UMR 7199, 74 route du Rhin, 67401 Illkirch, France.
Chemical & pharmaceutical bulletin.Chem Pharm Bull (Tokyo).2009 Nov;57(11):1300-2.
A short and straightforward synthesis of the antihistaminic drug mequitazine is reported, based on an efficient palladium catalyzed allylic alkylation of 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate using sodium phenothiazinate in mild conditions.
PMID 19881287

Japanese Journal

Expedient Synthesis of Mequitazine an Antihistaminic Drug by Palladium Catalyzed Allylic Alkylation of Sodium Phenothiazinate

Gonnot Vanessa,Nicolas Marc,Mioskowski Charles,Baati Rachid
CHEMICAL & PHARMACEUTICAL BULLETIN 57(11), 1300-1302, 2009
… A short and straightforward synthesis of the antihistaminic drug mequitazine is reported, based on an efficient palladium catalyzed allylic alkylation of 1-aza-bicyclo[2.2.2]oct-2-en-3-ylmethyl acetate using sodium phenothiazinate in mild conditions. …
NAID 130000124828

Intact Cell Binding for In Vitro Prediction of Sedative and Non-sedative Histamine H_1-Receptor Antagonists Based on Receptor Internalization

HISHINUMA Shigeru,SATO Yuko,KOBAYASHI Yusuke,KOMAZAKI Hiroshi,SAITO Masaki
Journal of pharmacological sciences 107(1), 66-79, 2008-05-20
… In contrast, the displacement curves for non-sedative H1-receptor antagonists (mequitazine, bepotastine, olopatadine, epinastine, carebastine, desloratadine and fexofenadine) were changed by histamine pretreatment: two types of changes, i.e. a rightward shift in the monophasic curve or an increase in the proportion of the low affinity component of the biphasic curve, were prevented under hypertonic conditions, in which clathrin-mediated receptor internalization is known to be inhibited. …
NAID 10024320504

「メキタジン」

Mequitazine
Systematic (IUPAC) name
	10-(4-azabicyclo[2.2.2] oct-7-ylmethyl) phenothiazine
Clinical data
Trade names	Primalan
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Registry Number	29216-28-2
ATC code	R06AD07
PubChem	CID 4066
DrugBank	DB01071
ChemSpider	3926
UNII	Y463242LY2
KEGG	D01324
Chemical data
Formula	C20H22N2S
Molecular mass	322.468 g/mol
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　　[★]

英: mequitazine
商: アリマン、キタゼミン、シークナロン、ゼスラン、ニポラジン、ハレムニン、ヒスポラン、ベナンザール、メキタゼノン、メキタミン
関: 抗ヒスタミン薬

第二世代抗ヒスタミン薬
フェノチアジン系。持続性ヒスタミンH1受容体拮抗薬
中枢作用弱い。鎮静作用弱い。
拮抗作用

ヒスタミン、アセチルコリン、ロイコトリエン、セロトニンなどの化学伝達物質

遊離抑制作用

ヒスタミン、ロイコトリエン

匿名

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案内

案内

mequitazine