Xylometazoline

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.  ?
Legal status  ?
Routes Intranasal spray or drops
Pharmacokinetic data
Half-life very short
Identifiers
CAS number 526-36-3 YesY
ATC code R01AA07 S01GA03
PubChem CID 5709
IUPHAR ligand 517
DrugBank DB06694
ChemSpider 5507 YesY
UNII WPY40FTH8K N
KEGG D08684 YesY
ChEMBL CHEMBL312448 YesY
Chemical data
Formula C16H24N2 
Mol. mass 244.37516 g/mol
SMILES eMolecules & PubChem
 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 dose being 0.1% w/v xylometazoline, and the dose for children under 12 being 0.05%.[citation needed]

Contents

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.[2] 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.[3] 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.

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, Sinutab Nasal Spray, Snup akut, Sudafed, Xylo-COMOD, Xylovit, Zolynd (in Serbia), Xynosine (in Pakistan), Xymelin and Zymelin.

Chemistry

Xylometazoline synthesis.png

See also

References

  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. ^ 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
  3. ^ Gold Standard Clinical Pharmacology

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Look at other dictionaries:

  • xylometazoline — noun A drug used as a topical nasal decongestant that works by constricting the blood vessels in the nose. Syn: xylomethazoline …   Wiktionary

  • xylometazoline — xy·lo·met·a·zo·line .zī lə .met ə zō .lēn n a sympathomimetic agent with vasoconstrictive activity that is used in the form of its hydrochloride C16H24N2·HCl esp. as a topical nasal decongestant * * * n. a sympathomimetic drug that constricts… …   Medical dictionary

  • xylometazoline — n. a sympathomimetic drug that constricts blood vessels (see vasoconstrictor). It is applied topically (in the form of drops or a spray) as a nasal decongestant for the relief of the common cold and sinusitis. Toxic effects are rare, but the… …   The new mediacal dictionary

  • xylometazoline hydrochloride — A sympathomimetic drug used as a nasal decongestant. * * * xy·lo·met·a·zo·line hy·dro·chlo·ride (zi″lo met″ə zoґlēn) [USP] an adrenergic used topically as a vasoconstrictor to reduce swelling and congestion of the nasal… …   Medical dictionary

  • Oxymetazoline — Systematic (IUPAC) name 3 (4,5 dihydro 1H …   Wikipedia

  • Pseudoephedrine — Systematic (IUPAC) name ( …   Wikipedia

  • Ephedrine — Systematic (IUPAC) name (R*,S*) 2 (methylamino) 1 phenylpro …   Wikipedia

  • Adrenergic receptor — Epinephrine Norepinephrine The adrenergic receptors (or adrenoceptors) are a class of met …   Wikipedia

  • Topical decongestant — Topical decongestants are decongestants applied directly to the nasal cavity. By applying them directly to the site of action, topical decongestants relieve nasal congestion while reducing the side effects associated with systemically acting… …   Wikipedia

  • Cathine — Not to be confused with caffeine, a compound found in coffee and tea. Cathine Systematic ( …   Wikipedia


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