Xylometazoline

Xylometazoline
Clinical data

Pronunciation	ZY-low-met-AH-zoh-leen
Trade names	Otrivin, Otrivine, others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	C
Dependence liability	Moderate
Routes of administration	Intranasal spray or drops, oral (capsules)
ATC code	R01AA07 (WHO) S01GA03 (WHO)
Legal status
Legal status	OTC
Pharmacokinetic data
Biological half-life	>10 seconds
Excretion	Urinary
Identifiers
IUPAC name 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]- 4,5-dihydro-1H-imidazole
CAS Number	526-36-3^N
PubChem (CID)	5709
IUPHAR/BPS	517
DrugBank	DB06694^Y
ChemSpider	5507^Y
UNII	WPY40FTH8K^Y
KEGG	D08684^Y
ChEMBL	CHEMBL312448^Y
ECHA InfoCard	100.007.629
Chemical and physical data
Formula	C₁₆H₂₄N₂
Molar mass	244.37516 g/mol
3D model (Jmol)	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)^Y Key:HUCJFAOMUPXHDK-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Xylometazoline, also known as xylomethazoline, and marketed under many brand names, is a medication which is used as a topical nasal decongestant.^[1] It is applied directly into the nose, either as a spray or as drops.

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).^[2] It should not be used for too long a period of time, or rebound effect may occur after discontinuation (see: rhinitis medicamentosa).

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[3]

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^[4] 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.^[5] 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.

Brand names

Xylometazoline is sold under a number of brand names worldwide, including: Antazol (Square,in Bangladesh), Xylomet (Opsonin, Bangladesh) Cirovin, Klarigen (in Denmark), Nasolin, Neo-Rinoleina, Novorin, Olynth, Otrinoz, Otriven, Otrivin (South Africa, Sweden, Norway, Netherlands, Vietnam), Otrivine, Otrix, Rhinoset,Zenfresh, Otrivin, Nasomist-X (in India), Naphthyzinium, Xymelyn (in Latvia), Sinutab Nasal Spray, Snup akut, Sudafed, Xylo-COMOD, Xylolin (in UAE), Xylovit, Olynth (in Serbia), Xynosine (in Pakistan, Afghanistan, Kyrgyzstan and Kazakhstan), Xymelin, Zymelin, Xylostar, Xylorin (in Poland), Nasobol, Xylo Mepha and others (Switzerland), and Decozal (in Jordan).

References

↑ Eccles, R.; Eriksson, M.; Garreffa, S.; Chen, S. (2008). "The nasal decongestant effect of xylometazoline in the common cold". American journal of rhinology. 22 (5): 491–496. doi:10.2500/ajr.2008.22.3202. PMID 18655753.
↑ http://www.drugs.com/mtm/xylometazoline-nasal.html
↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
↑ Haenisch, B.; Walstab, J.; Herberhold, S.; Bootz, F.; Tschaikin, M.; Ramseger, R.; Bönisch, H. (2009). "Alpha-adrenoceptor Agonistic Activity of Oxymetazoline and Xylometazoline". Fundamental & Clinical Pharmacology. 24 (6): 729–39. doi:10.1111/j.1472-8206.2009.00805.x. PMID 20030735.
↑ Gold Standard Clinical Pharmacology

Adrenergic receptor modulators

α₁

Agonists 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline

Antagonists Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone) Benoxathian Buflomedil Bunazosin Carvedilol Corynanthine Dapiprazole Domesticine Doxazosin Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride) Etoperidone Eugenodilol Fenspiride Hydroxyzine Indoramin Ketanserin L-765,314 Labetalol mCPP Mepiprazole Metazosin Monatepil Moxisylyte Naftopidil Nantenine Nefazodone Neldazosin Niaprazine Nicergoline Niguldipine Pardoprunox Pelanserin Phendioxan Phenoxybenzamine Phentolamine Piperoxan Prazosin Quinazosin Ritanserin Silodosin Spiperone Talipexole Tamsulosin Terazosin Tiodazosin Tolazoline Trazodone Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine) Trimazosin Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Urapidil WB-4101 Zolertine

α₂

Agonists (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rilmenidine Romifidine Talipexole Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil XP21279 Xylazine Xylometazoline

Antagonists 1-PP Adimolol Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine) Azapirones (e.g., buspirone, tandospirone) BRL-44408 Buflomedil Cirazoline Efaroxan Esmirtazapine Fenmetozole Fluparoxan Idazoxan mCPP Mianserin Mirtazapine NAN-190 Olanzapine Pardoprunox Phentolamine Phenoxybenzamine Piperoxan Piribedil Rauwolscine Rotigotine SB-269970 Setiptiline Spiroxatrine Sunepitron Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine

Agonists Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol

Antagonists Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

See also: Dopaminergics

Melatonergics

Serotonergics

Monoamine reuptake and release modulators

Monoamine metabolism modulators

Monoamine neurotoxins

Decongestants and other nasal preparations (R01)

Topical

Sympathomimetics, plain	Cyclopentamine Ephedrine Epinephrine Fenoxazoline Levomethamphetamine Metizoline Naphazoline Oxymetazoline Phenylephrine Propylhexedrine Tetryzoline Tramazoline Tuaminoheptane Tymazoline Xylometazoline

Antiallergic agents, excluding corticosteroids	Spaglumic acid histamine antagonists (Levocabastine Antazoline Thonzylamine) mast cell stabilizer (some are also antihistamines) (Cromoglicic acid Nedocromil Azelastine Olopatadine Lodoxamide)

Corticosteroids	Beclometasone dipropionate Betamethasone Budesonide Ciclesonide Dexamethasone Flunisolide Fluticasone Mometasone furoate Prednisolone Tixocortol Triamcinolone

Other nasal preparations	Cafaminol Calcium hexamine thiocyanate Eucalyptus oil Framycetin Hexamidine Hyaluronan Ipratropium bromide Mupirocin Retinol Ritiometan Saline water

Systemic use:
Sympathomimetics

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Xylometazoline

Mechanism of action

Brand names

See also

References