xylometazoline

キシロメタゾリン

関

xylometazoline hydrochloride

同

Otrivin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/12 21:15:03」(JST)

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Xylometazoline

Systematic (IUPAC) name
2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]- 4,5-dihydro-1H-imidazole
Clinical data
Trade names	Otrivin
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	C
Legal status	Not known
Routes	Intranasal spray or drops, oral (capsules)
Pharmacokinetic data
Half-life	>10 seconds
Excretion	Urinary
Identifiers
CAS number	526-36-3 N
ATC code	R01AA07 S01GA03
PubChem	CID 5709
IUPHAR ligand	517
DrugBank	DB06694
ChemSpider	5507 Y
UNII	WPY40FTH8K Y
KEGG	D08684 Y
ChEMBL	CHEMBL312448 Y
Chemical data
Formula	C16H24N2
Mol. mass	244.37516 g/mol
SMILES N\1=C(\NCC/1)Cc2c(cc(cc2C)C(C)(C)C)C
InChI InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18) Y Key:HUCJFAOMUPXHDK-UHFFFAOYSA-N Y
N (what is this?)  (verify)

Xylometazoline (also known as xylomethazoline) is a drug which is used as a topical nasal decongestant. It is applied directly into the nose, either as a spray or as drops.

Xylometazoline is marketed under many brand names (see below), with the typical adult solution strength being 0.1% w/v xylometazoline, and the dose for children under 12 being 0.05%.^{[citation needed]}

It should not be used for too long a period of time, or rebound effect may occur after discontinuation (see: Rhinitis medicamentosa).

Mechanism of action

The drug works by constricting the blood vessels in the nose. The vasoconstriction means that there is less pressure in the capillaries and less water can filter out, thus less discharge is made. (If the colour of the nasal passage is observed, it is visibly paler after dosage.)

Xylometazoline is an imidazole derivative which is designed to mimic the molecular shape of adrenaline. It binds to alpha-adrenergic receptors in the nasal mucosa. Due to its sympathomimetic effects, it should not be used by people with high blood pressure, or other heart problems.

Extended usage of xylometazoline can result in decreased effectiveness or a build up of tolerance against the drug. The number of receptors decreases, and when the administration of the drug is ceased, chronic congestion can occur; this is called rhinitis medicamentosa, commonly referred to as rebound congestion. Moreover long-term overdosing can cause degenerative changes in nasal mucous membranes that pose another health problem^{[citation needed]}.

Brand names

Xylometazoline is sold under a number of brand names worldwide, including: Xylomet(Opsonin,BD)Cirovin, Klarigen (in Denmark), Nasolin, Neo-Rinoleina, Novorin, Olynth, Otrinoz, Otriven, Otrivin, Otrivine, Otrix, Rhinoset, Nosikind (in India), Sinutab Nasal Spray, Snup akut, Sudafed, Xylo-COMOD, Xylovit, Zolynd (in Serbia), Xynosine (in Pakistan, Afghanistan, Kyrighistan and Kazakhistan), Xymelin,and Zymelin.In India it is marketed by Intas under the trade name 'Xylostar'.

Chemistry

• H. Albrecht, U.S. Patent 2,868,802 (1959).
• H. Albrecht, DE 1049387  (1957).

See also

• Oxymetazoline

References

UpToDate Contents

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• Dexpanthenol: An Overview of its Contribution to Symptom Relief in Acute Rhinitis Treated with Decongestant Nasal Sprays.

• Mösges R1, Shah-Hosseini K1, Hucke HP2, Joisten MJ3.
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• Fathy ME1, Abo El Abass Mohamed S1, Elmansi H2, Belal F1.
• Journal of chromatographic science.J Chromatogr Sci.2017 Jan;55(1):14-22. Epub 2016 Sep 12.
• PMID 27621136

Japanese Journal

• A comparison of the effect of xylometazoline on nasal airflow, and on blood flux as measured by laser doppler flowmetry

• WRIGHT RG
• Acta Otolaryngol (Stockh) 108, 284-289, 1989
• NAID 30033841113

• 2-(4'-tert.-Butyl-2'4'-dimethl-phenyl-methyl)-imidazoline Hydrichloride (Xylometazoline) に関する薬理学的研究

• 森本 史郎,田中 宏
• 大阪市医学会雑誌 18(3/4), 211-220, 1969-04
• NAID 110001799266

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