Xylometazoline

Xylometazoline
Clinical data
Pronunciation	/ˌzaɪloʊˌmɛtəˈzoʊliːn/; ZY-lo-MET-ə-ZOH-leen
Trade names	Otrivin, Otrivine, others
AHFS/Drugs.com	Monograph
MedlinePlus	a608026
License data	US DailyMed: Xylometazoline;
Dependence; liability	Moderate
Routes of; administration	intranasal (spray or drops)
Drug class	α1 and α2 Adrenergic receptor agonist,; Decongestant
ATC code	R01AA07 (WHO) S01GA03 (WHO);
Legal status
Legal status	UK: General sales list (GSL, OTC) ; US: OTC;
Pharmacokinetic data
Elimination half-life	2–3 hours
Excretion	Urinary
Identifiers
	IUPAC name 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-; 4,5-dihydro-1H-imidazole;
CAS Number	526-36-3 ;
PubChem CID	5709;
IUPHAR/BPS	517;
DrugBank	DB06694 ;
ChemSpider	5507 ;
UNII	WPY40FTH8K;
KEGG	D08684 ;
ChEMBL	ChEMBL312448 ;
CompTox Dashboard (EPA)	DTXSID8046957 ;
ECHA InfoCard	100.007.629
Chemical and physical data
Formula	C16H24N2
Molar mass	244.382 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N\1=C(\NCC/1)Cc2c(cc(cc2C)C(C)(C)C)C;
	InChI InChI=1S/C16H24N2/c1-11-8-13(16(3,4)5)9-12(2)14(11)10-15-17-6-7-18-15/h8-9H,6-7,10H2,1-5H3,(H,17,18) ; Key:HUCJFAOMUPXHDK-UHFFFAOYSA-N ;
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Xylometazoline, also spelled xylomethazoline, is a medication used to reduce symptoms of nasal congestion, allergic rhinitis, and sinusitis.^[3] It is used directly in the nose as a spray or drops.^[4]

Side effects include trouble sleeping, irritation of the nose, nausea, nosebleed (3%), period pain (10%) and headache (3%).^[5]^[3]^[4] Long term use (> 10 days) is not recommended due to a rhinitis medicamentosa when stopped.^[5]^[6] Use is not recommended during pregnancy.^[3] Xylometazoline is in the decongestant and alpha-adrenergic agonist families of medication.^[6]^[7]

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.^[8]

Xylometazoline was patented in 1956 and came into medical use in 1959.^[9]^[10] It is on the World Health Organization's List of Essential Medicines.^[11] Xylometazoline is available as a generic medication.^[4]

^ Fulga A, Zenovia A, Ene DC, Stan C, Firescu D, Fulga I (18 November 2021). "Fulga, Ana, Andrei Zenovia, Doriana Cristea Ene, Constantin Stan, Dorel Firescu, and Iuliu Fulga. 2021. "Addiction to Nasal Decongestants Based on Α-Adrenoceptor Agonists Case Series and Literature Review: Array". EuroEconomica 40 (2)". Euroeconomica. 40 (2).
^ https://bnf.nice.org.uk/drugs/xylometazoline-hydrochloride/medicinal-forms/#spray
^ ^a ^b ^c "Otrivine Adult Measured Dose Sinusitis Spray - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. 13 April 2016. Archived from the original on 29 December 2016. Retrieved 28 December 2016.
^ ^a ^b ^c British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 786. ISBN 978-0-85711-156-2.
^ ^a ^b Eccles R, Martensson K, Chen SC (April 2010). "Effects of intranasal xylometazoline, alone or in combination with ipratropium, in patients with common cold". Current Medical Research and Opinion. 26 (4): 889–899. doi:10.1185/03007991003648015. PMID 20151787. S2CID 34728458.
^ ^a ^b Graf P (1997). "Rhinitis medicamentosa: aspects of pathophysiology and treatment". Allergy. 52 (40 Suppl): 28–34. doi:10.1111/j.1398-9995.1997.tb04881.x. PMID 9353558. S2CID 72326981.
^ "Xylometazoline nasal medical facts from Drugs.com". www.drugs.com. Archived from the original on 29 December 2016. Retrieved 28 December 2016.
^ Proudman RG, Akinaga J, Baker JG (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". Pharmacology Research & Perspectives. 10 (5): e01003. doi:10.1002/prp2.1003. PMC 9471048. PMID 36101495.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 552. ISBN 978-3-527-60749-5. Archived from the original on 29 December 2016.
^ US patent 2868802A, Hüni, Albrecht, "2-(γ-TERT-BUTYL-O,O'-DIMETHYL-PHENYL-METHYL)-IMIDAZOLINE AND SALTS", issued 13 January 1959, assigned to Ciba Pharmaceutical Products Inc., Summit, N. J.
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

[1] Fulga A, Zenovia A, Ene DC, Stan C, Firescu D, Fulga I (18 November 2021). "Fulga, Ana, Andrei Zenovia, Doriana Cristea Ene, Constantin Stan, Dorel Firescu, and Iuliu Fulga. 2021. "Addiction to Nasal Decongestants Based on Α-Adrenoceptor Agonists Case Series and Literature Review: Array". EuroEconomica 40 (2)". Euroeconomica. 40 (2).

[2] ttps://bnf.nice.org.uk/drugs/xylometazoline-hydrochloride/medicinal-forms/#spray

[UK2016-3] "Otrivine Adult Measured Dose Sinusitis Spray - Summary of Product Characteristics (SPC) - (eMC)". www.medicines.org.uk. 13 April 2016. Archived from the original on 29 December 2016. Retrieved 28 December 2016.

[BNF69-4] British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 786. ISBN 978-0-85711-156-2.

[sideeff-5] Eccles R, Martensson K, Chen SC (April 2010). "Effects of intranasal xylometazoline, alone or in combination with ipratropium, in patients with common cold". Current Medical Research and Opinion. 26 (4): 889–899. doi:10.1185/03007991003648015. PMID 20151787. S2CID 34728458.

[Gra1997-6] Graf P (1997). "Rhinitis medicamentosa: aspects of pathophysiology and treatment". Allergy. 52 (40 Suppl): 28–34. doi:10.1111/j.1398-9995.1997.tb04881.x. PMID 9353558. S2CID 72326981.

[MTM2016-7] "Xylometazoline nasal medical facts from Drugs.com". www.drugs.com. Archived from the original on 29 December 2016. Retrieved 28 December 2016.

[8] Proudman RG, Akinaga J, Baker JG (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". Pharmacology Research & Perspectives. 10 (5): e01003. doi:10.1002/prp2.1003. PMC 9471048. PMID 36101495.

[Fis2006-9] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 552. ISBN 978-3-527-60749-5. Archived from the original on 29 December 2016.

[10] US patent 2868802A, Hüni, Albrecht, "2-(γ-TERT-BUTYL-O,O'-DIMETHYL-PHENYL-METHYL)-IMIDAZOLINE AND SALTS", issued 13 January 1959, assigned to Ciba Pharmaceutical Products Inc., Summit, N. J.

[WHO23rd-11] World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.

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