Xylometazoline

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Xylometazoline
Xylometazoline Structural Formulae V 2.png
Xylometazoline ball-and-stick animation.gif
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
  • OTC
Moderate
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 YesY
UNII WPY40FTH8K YesY
KEGG D08684 YesY
ChEMBL CHEMBL312448 YesY
Chemical data
Formula C16H24N2 
Mol. mass 244.37516 g/mol
 N (what is this?)  (verify)

Xylometazoline (also known as xylomethazoline) is a drug which is used as a topical nasal decongestant.[1] 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). It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[2]

Mechanism of action[edit]

The drug works by constricting the blood vessels in the nose. The decongestant effect is due to constriction of large veins in the nose which swell up during the inflammation of any infection or allergy of the nose. The smaller arteries are also constricted and this causes the colour of the nasal epithelium to be 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.[3] 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 buildup of tolerance against the drug.[4] 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[edit]

Xylometazoline is sold under a number of brand names worldwide, including: Antazol (Square, BD), 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, Olynth (in Serbia), Xynosine (in Pakistan, Afghanistan, Kyrighistan and Kazakhistan), Xymelin, and Zymelin. In India it is marketed by Intas under the trade name Xylostar. In Switzerland: Kompendium, Decozal (in Jordan).

Chemistry[edit]

Xylometazoline synthesis.png

See also[edit]

References[edit]

  1. ^ Eccles, R.; Eriksson, M.; Garreffa, S.; Chen, S. (2008). "The nasal decongestant effect of xylometazoline in the common cold". American journal of rhinology 22 (5): 491–496. doi:10.2500/ajr.2008.22.3202. PMID 18655753.  edit
  2. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ Haenisch, B.; Walstab, J.; Herberhold, S.; Bootz, F.; Tschaikin, M.; Ramseger, R.; Bönisch, H. (2009). "Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline". Fundamental & clinical pharmacology 24 (6): 729–739. doi:10.1111/j.1472-8206.2009.00805.x. PMID 20030735.  edit
  4. ^ Gold Standard Clinical Pharmacology