Xylometazoline, also spelled xylomethazoline, is a medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis.[
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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.
Mechanism of action
Xylometazoline works by stimulating adrenergic receptors on the lamina propria of in the nose. The decongestant effect is due to Vasoconstriction 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 α1 and α2 adrenergic receptors
Extended usage of xylometazoline can result in decreased effectiveness or a buildup of tolerance against the drug.
Society and culture
In 2021, a US FDA Drug Safety Communication stated that, while a US Consumer Product Safety Commission (CPSC) proposed rule regarding child-resistant packaging covered products containing xylometazoline, no such products were marketed in the United States at that time.
Brand names
The most common name for over-the-counter products containing xylometazoline internationally is "Otrivin" (used in Australia,
Other product names used include Antazol (Square, in Bangladesh), Xylomet (Opsonin, Bangladesh), Cirovin, Klarigen (in Denmark), Nasolin (in Finland), Neo-Rinoleina, Novorin, Olynth, Otrinoz, Galazolin (Russia, Ukraine, Belarus), Nasomist-X, Otrix, Rhinoset, Zenfresh, Naphthyzinium, Xymelyn (in Latvia), Sinutab Nasal Spray, Snup akut, Sudafed, Xylo-COMOD, Xylolin (in the United Arab Emirates), Xylovit, Olynth (in Serbia, the Czech Republic, Lithuania and Slovakia), Meralys (in Croatia) Xynosine (in Pakistan, Afghanistan, Kyrgyzstan and Kazakhstan), Xymelin, Zymelin, Xylostar, Xylorin (in Poland), Nasobol, Xylo Mepha and others (Switzerland), Decozal (in Jordan), Nasic, Orinox (Romania), Narhimed, Actifed (Italy), nasa Rhinathiol (Belgium), Zolinol, Nasorhinathiol, and Vibrocil (Portugal).
Formulations
The standard adult solution strength is 0.1% w/v xylometazoline (or 1 mg per 1 mL solution).
Synthesis
5-tert-Butyl-m-xylene is reacted with chloromethyl methyl ether in the presence of zinc chloride to form 2,6-dimethyl-4-tert-butyl-benzylchloride, which is then reacted with sodium cyanide in the presence of potassium iodide to produce 2,6-dimethyl-4-tert-butyl-benzylcyanide. This is then reacted with ethylene diamine in the presence of para-toluenesulfonic acid to form the corresponding imidazoline, this being xylometazoline.
