Xylometazoline

Structural formula
General
Non-proprietary name	Xylometazoline
other names	2 - {[4- (1,1-dimethylethyl) -2,6-dimethylphenyl] methyl} -4,5-dihydro-1 H -imidazole
Molecular formula	C 16 H 24 N 2
External identifiers / databases
CAS number 526-36-3 1218-35-5 ( monohydrochloride ) PubChem 5709 DrugBank DB06694 Wikidata Q31030
Drug information
ATC code	R01 AA07 R01 AB06 S01 GA03
Drug class	Sympathomimetic
Mechanism of action	α 1 -adrenoceptor - agonist
properties
Molar mass	244.38 g mol −1
Melting point	131-133 ° C 327–329 ° C ( hydrochloride )
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Monohydrochloride danger H and P phrases H: 301 P: 301 + 310
Toxicological data	230 mg kg −1 ( LD 50 ,  rat ,  oral , hydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Xylometazoline is a chemical compound from the group of imidazole derivatives. It is used as a medicinal substance to reduce the swelling of the nasal mucosa . As a direct α-sympathomimetic is both an α ₁ -adrenoceptor - agonist and an α ₂ -adrenoceptor - agonist and causes the contraction of smooth muscle . As a result, the locally located blood vessels in the nose are narrowed ( vasoconstriction ) and the reduced blood flow causes the mucous membranes to swell. Xylometazoline is therefore used in nasal sprays , nasal ointments and nasal drops .

Development and marketing

Xylometazoline was first synthesized by Albrecht Hüni from Basel at the pharmaceutical company CIBA AG and a patent was applied for in 1959. Grant of a patent in Switzerland took place in 1961. There are now several xylometazolinhaltige runny nose sprays and gobs as generic available. In Germany, Austria and Switzerland, xylometazoline requires pharmacy, but does not require a prescription.

effect

Xylometazoline works in a similar way to adrenaline and binds to the same receptors . After absorption through the nasal mucous membranes, it first develops local effects on the α-receptors in the blood vessels of the nasal mucous membrane (this causes the swelling) and then also has a systemic effect. For this reason, it should not be used by patients with high blood pressure or other heart problems. Respiratory depression and comatose conditions are possible in infants and young children . As far as we know today, use during pregnancy is not contraindicated within the therapeutic dose range .

Side effects

The following side effects can occur:

• Respiratory tract - often (1–10%): Xylometazoline can cause temporary mild irritation (burning sensation or dryness of the nasal mucosa), especially in sensitive patients. After its effects, the drug can lead to increased swelling of the mucous membranes (reactive hyperemia ). Prolonged or frequent use and higher doses of xylometazoline lead to tolerance development (habituation) and can lead to burning or dryness of the mucous membrane within the nose as well as reactive congestion with rhinitis medicamentosa (medicinal rhinitis ). This effect can already occur after 5 days of treatment and, after continued use, cause permanent damage to the mucous membrane with crust formation ( rhinitis sicca ).
• Nervous system - Rarely (0.01–0.1%): headache, insomnia - also fatigue.
• Heart and circulatory system: When used locally in the nose, systemic side effects such as palpitations, increased pulse rate, rise in blood pressure occur occasionally (0.1–1%).
• Effects on drivers and the operation of machines: With prolonged use or high doses of xylometazoline, systemic effects with an impact on the cardiovascular system and central nervous side effects cannot be ruled out. In these cases, the ability to drive a motor vehicle and operate machines may be impaired.

Trade names

Monopreparations
Balkis (D), GeloNasal (D), Hysan (D), Imidin (D), Nasben (CH), Nasobol (CH), Olynth (D, A), Otriven (D), Otrivin (A, CH), Rapako xylo (D), RatioSoft (A), Rhinostop (CH), Rinosedin (CH), Schnupfen Endrine (D), Snup (D), numerous generics (D, A, CH)

Combination preparations

• with dexpanthenol : Nasic (A, CH, D), NasenDuo Ratiopharm (D)
• with ipratropium bromide : Otrivin Duo (A)
• with carbocysteine : Triofan (CH)

Individual evidence

1. ↑ ^{a b c} Process for the preparation of a new nitrogen-containing, heterocyclic compound. Patent specification No. 3574401 of the Federal Office for Intellectual Property dated October 15, 1961.
2. ↑ ^{a b} Data sheet Xylometazoline hydrochloride from Sigma-Aldrich , accessed on April 25, 2011 ( PDF ).
3. ↑ Data sheet XYLOMETAZOLINE HYDROCHLORIDE CRS (PDF) at EDQM , accessed on March 8, 2009.
4. ↑ Process for the preparation of a new imidazoline. Patent specification No. 1 049 387 of the German Patent Office from July 30, 1959.
5. ↑ Coma in newborns due to decongestant nasal drops? In: Deutsches Ärzteblatt , December 15, 2006.
6. ↑ Xylometazoline. In: www.embryotox.de. Retrieved December 18, 2018 . 
7. ↑ Information for professionals, NasenSpray-ratiopharm adults. In: www.ratiopharm.de. Retrieved December 18, 2018 . 
8. ^ Peter Graf: Rhinitis Medicamentosa . In: Treatments in Respiratory Medicine . tape 4 , no. 1 , 2012, p. 21-29 , doi : 10.2165 / 00151829-200504010-00003 .

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !