2-(4-TERT-BUTYL-2,6-DIMETHYL-BENZYL)-4,5-DIHYDRO-1H-IMIDAZOLE

Absorption

No information is available on xylometazoline pharmacokinetics.

Toxicity

The oral LD50 is 230 mg/kg in rats and 75 mg/kg in mice. The subcutaneous LD50 is 90 mg/kg in rats and 53 mg/kg in mice. The intraperitoneal LD50 is 43 mg/kg in rats.
Xylometazoline poisoning is documented in three pediatric patients who were exposed to a drug concentration 40 times above the adequate dosage for children due to a compounding error: these patients experienced bradypnea and sinus bradycardia with supraventricular extrasystoles and were managed with fluid management.

The Uses of 2-(4-TERT-BUTYL-2,6-DIMETHYL-BENZYL)-4,5-DIHYDRO-1H-IMIDAZOLE

Adrenergic (vasoconstrictor).

The Uses of 2-(4-TERT-BUTYL-2,6-DIMETHYL-BENZYL)-4,5-DIHYDRO-1H-IMIDAZOLE

Xylometazoline is used for rhinitis, laryngitis, sinusitis, inflammation of antrum of Highmore, and allergic illnesses of the nasal cavity and throat.

Background

Xylometazoline is an imidazoline derivative with sympathomimetic and nasal decongestant activity. Xylometazoline works by binding to alpha (α)-adrenergic receptors to cause vasoconstriction of nasal blood vessels.
Xylometazoline is available in over-the-counter (OTC) nasal sprays or drops to temporarily relieve nasal congestion due to cold, hay fever or other respiratory allergies. In some countries, it is available as combination products with ipratropium, domiphen, or dexpanthenol.

Indications

Xylometazoline is indicated for the temporary relief of nasal congestion due to cold, hay fever or other respiratory allergies.

Definition

ChEBI: Xylometazoline is an alkylbenzene.

brand name

Neo-Synephrine II (Sterling Winthrop); Otrivin Hydrochloride (Ciba-Geigy).

Pharmacokinetics

Xylometazoline is a sympathomimetic agent that causes vasoconstriction of the nasal mucosa. In one study comprising subjects with nasal congestion associated with the common cold, the median time of onset of subjective relief of nasal congestion was about 1.7 minutes and the time of subjective peak relief of nasal congestion was 30 minutes. Previous studies reported rebound swelling, rebound nasal congestion, rhinitis medicamentosa, and shorter duration of decongestant effect from the long-term use of xylometazoline in healthy volunteers, suggesting that the drug is most effective if used temporarily.
An early in vitro study demonstrated xylometazoline to exert anti-oxidant actions, where it inhibited microsomal lipid peroxidation and mediated hydroxyl radical scavenging activity. This suggests that xylometazoline has a beneficial effect against oxidants, which play a role in tissue damage in inflammation.

Synthesis

Xylometazoline, 2-(4-tert-butyl-2,6-dimethylbenzyl)-2-imidazoline (11.1.40), is also synthesized in a single reaction by cyclocondensation of 4-tert-butyl-2,6- dimethylbenzylcyanide with ethylendiamine [43,44].

Metabolism

No information is available on xylometazoline pharmacokinetics.