Chemistry:Xylometazoline

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Short description: Nasal decongestant
Xylometazoline
Xylometazoline.svg
Clinical data
Pronunciation/ˌzaɪloʊˌmɛtəˈzoʊliːn/
ZY-lo-MET-ə-ZOH-leen
Trade namesOtrivin, Otrivine, others
AHFS/Drugs.comMonograph
MedlinePlusa608026
License data
Pregnancy
category
  • C
Dependence
liability		Moderate
Routes of
administration		intranasal (spray or drops)
Drug classα1 and α2 adrenergic receptor agonist
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life>10 seconds
ExcretionUrinary
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC16H24N2
Molar mass244.382 g·mol−1
3D model (JSmol)
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Xylometazoline, also spelled xylomethazoline, is a medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis.[1] Use is not recommended for more than seven days.[2] Use is also not recommended in those less than three months of age and some say not less than 6 years of age.[2][3] It is used directly in the nose as a spray or drops.[2]

Side effects include trouble sleeping, irritation of the nose, nausea, nosebleed (3%), period pain (10%) and headache (3%).[4][1][2] Long term use (> 10 days) is not recommended due to a rhinitis medicamentosa when stopped.[4][5] Use is not recommended during pregnancy.[1] Xylometazoline is in the decongestant and alpha-adrenergic agonist families of medication.[5][6]

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.[7]

Xylometazoline was patented in 1956 and came into medical use in 1959.[8][9] It is on the World Health Organization's List of Essential Medicines.[3][10] Xylometazoline is available as a generic medication.[2]

Mechanism of action

The drug works by stimulating adrenergic receptors on the lamina propria of 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 α1 and α2 adrenergic receptors[11] in the nasal mucosa. 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.[12] 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]

Society and culture

Brand names

The most common name for over-the-counter products containing xylometazoline internationally is "Otrivin" (used in Australia,[13] Canada, Estonia, Greece, Hungary, India,[14] Israel, Jordan, Netherlands, New Zealand, Norway, Poland, South Africa, Sweden, Vietnam, Hong Kong), "Otrivine" (United Kingdom, Ireland, Turkey, Belgium), or "Otriven" (Germany). A product marketed as "Otrivin Oxy" contains oxymetazoline instead of xylometazoline.

Other product names used include Antazol (Square, in Bangladesh), Xylomet (Opsonin, Bangladesh), Cirovin, Klarigen (in Denmark), Nasolin, Neo-Rinoleina, Novorin, Olynth, Otrinoz, Galazolin[15] (Russia, Ukraine, Belarus), Nasomist-X, Otrix, Rhinoset, Zenfresh, Naphthyzinium, Xymelyn (in Latvia), Sinutab Nasal Spray, Snup akut, Sudafed, Xylo-COMOD, Xylolin (in UAE), Xylovit, Olynth (in Serbia 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 (Italy), nasa Rhinathiol (Belgium) and Zolinol,[16] Nasorhinathiol[17] and Vibrocil[18] (Portugal).

As of 2021, a number of consumer products containing xylometazoline are marketed in the United States.[19]

Formulations

The standard adult solution strength is 0.1% w/v xylometazoline (or 1 mg per 1 mL solution), and the dose for children under 12 is usually 0.05% (0.5 mg/mL).[20]

See also

References

  1. ↑ 1.0 1.1 1.2 "Otrivine Adult Measured Dose Sinusitis Spray - Summary of Product Characteristics (SPC) - (eMC)". 13 April 2016. https://www.medicines.org.uk/emc/medicine/21058. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 786. ISBN 9780857111562. 
  3. ↑ 3.0 3.1 World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 2019. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO. 
  4. ↑ 4.0 4.1 "Effects of intranasal xylometazoline, alone or in combination with ipratropium, in patients with common cold". Current Medical Research and Opinion 26 (4): 889–899. April 2010. doi:10.1185/03007991003648015. PMID 20151787. 
  5. ↑ 5.0 5.1 "Rhinitis medicamentosa: aspects of pathophysiology and treatment". Allergy 52 (40 Suppl): 28–34. 1997. doi:10.1111/j.1398-9995.1997.tb04881.x. PMID 9353558. 
  6. ↑ "Xylometazoline nasal medical facts from Drugs.com". https://www.drugs.com/mtm/xylometazoline-nasal.html. 
  7. ↑ Proudman, Richard G. W.; Akinaga, Juliana; Baker, Jillian G. (October 2022). "The signaling and selectivity of α‐adrenoceptor agonists for the human α2A , α2B and α2C ‐adrenoceptors and comparison with human α1 and β‐adrenoceptors" (in en). Pharmacology Research & Perspectives 10 (5). doi:10.1002/prp2.1003. ISSN 2052-1707. PMID 36101495. PMC 9471048. https://bpspubs.onlinelibrary.wiley.com/doi/10.1002/prp2.1003. 
  8. ↑ (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 552. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA552. 
  9. ↑ , Albrecht"2-(γ-TERT-BUTYL-O,O'-DIMETHYL-PHENYL-METHYL)-IMIDAZOLINE AND SALTS" US patent 2868802A, issued 1959-01-13, assigned to Ciba Pharmaceutical Products Inc., Summit, N. J.
  10. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  11. ↑ "Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline". Fundamental & Clinical Pharmacology 24 (6): 729–739. December 2010. doi:10.1111/j.1472-8206.2009.00805.x. PMID 20030735. 
  12. ↑ Gold Standard Clinical Pharmacology
  13. ↑ "xylometazoline". https://www.healthdirect.gov.au/medicines/medicinal-product/aht,21627/xylometazoline. 
  14. ↑ "Otrivin | GSK Consumer Healthcare INDIA" (in en-GB). https://india-consumer.gsk.com/en-in/products/otrivin/. 
  15. ↑ "Галазолин (Galazolin) - инструкция по применению, состав, аналоги препарата, дозировки, побочные действия". https://www.rlsnet.ru/tn_index_id_7788.htm. 
  16. ↑ "Zolinol® - Edol". https://edol.pt/en/produto/zolinol/. 
  17. ↑ "Nasorhinathiol, 0,5 mg/mL-15 mL x 1 sol pulv nasal". https://www.farmaciasportuguesas.pt/nasorhinathiol-0-5-mg-ml-15-ml-x-1-sol-pulv-nasal-9679720.html. 
  18. ↑ "Vibrocil Actilong Mentol". https://www.vibrocil.pt/produtos-vibrocil/vibrocil-actilong-mentol-descongestionante-nasal.html. 
  19. ↑ "FDA Drug Safety Communication: Serious adverse events from accidental ingestion by children of over-the-counter eye drops and nasal sprays". FDA. July 2021. https://www.fda.gov/Drugs/DrugSafety/ucm325257.htm. 
  20. ↑ "Xylometazoline nasal Uses, Side Effects & Warnings". https://www.drugs.com/mtm/xylometazoline-nasal.html. 

External links



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