Xylometazoline

Xylometazoline
Clinical data
Pronunciation	/ˌzaɪloʊˌmɛtəˈzoʊliːn/; ZY-lo-MET-ə-ZOH-leen
Trade names	Otrivin, Otrivine, others
AHFS/Drugs.com	Monograph
MedlinePlus	a608026
License data	US DailyMed: Xylometazoline;
Pregnancy; category	C;
Dependence; liability	Moderate
Routes of; administration	intranasal (spray or drops)
Drug class	α1 and α2 adrenergic receptor agonist
ATC code	R01AA07 (WHO) S01GA03 (WHO);
Legal status
Legal status	In general: Over-the-counter (OTC);
Pharmacokinetic data
Elimination half-life	>10 seconds
Excretion	Urinary
Identifiers
	IUPAC name 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-; 4,5-dihydro-1H-imidazole;
CAS Number	526-36-3 ;
PubChem CID	5709;
IUPHAR/BPS	517;
DrugBank	DB06694 ;
ChemSpider	5507 ;
UNII	WPY40FTH8K;
KEGG	D08684 ;
ChEMBL	ChEMBL312448 ;
CompTox Dashboard (EPA)	DTXSID8046957 ;
ECHA InfoCard	100.007.629
Chemical and physical data
Formula	C16H24N2
Molar mass	244.382 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:HUCJFAOMUPXHDK-UHFFFAOYSA-N ;
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Xylometazoline, also spelled xylomethazoline, is a medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis. Use is not recommended for more than seven days. Use is also not recommended in those less than three months of age and some say not less than 6 years of age. It is used directly in the nose as a spray or drops.

Side effects include trouble sleeping, irritation of the nose, nausea, nosebleed (3%), period pain (10%) and headache (3%). Long term use (> 10 days) is not recommended due to a rhinitis medicamentosa when stopped. Use is not recommended during pregnancy. Xylometazoline is in the decongestant and alpha-adrenergic agonist families of medication.

One study classified it with selectivity ratios in alpha 2 adrenergic receptors of 151 for a2A vs a2B, 4.5 a2A vs a2C, and 33.9 a2B vs a2C. Making it a highly selective a2A agonist.

Xylometazoline was patented in 1956 and came into medical use in 1959. It is on the World Health Organization's List of Essential Medicines. Xylometazoline is available as a generic medication.

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