Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H24N2 |
Molecular Weight | 244.3752 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(=CC(C)=C1CC2=NCCN2)C(C)(C)C
InChI
InChIKey=HUCJFAOMUPXHDK-UHFFFAOYSA-N
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)
DescriptionSources: https://www.drugs.com/mtm/xylometazoline-nasal.htmlCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19085441 | https://clinicaltrials.gov/ct2/show/NCT00630474 | https://clinicaltrials.gov/ct2/show/NCT00452270 | https://www.ncbi.nlm.nih.gov/pubmed/20151787
Sources: https://www.drugs.com/mtm/xylometazoline-nasal.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19085441 | https://clinicaltrials.gov/ct2/show/NCT00630474 | https://clinicaltrials.gov/ct2/show/NCT00452270 | https://www.ncbi.nlm.nih.gov/pubmed/20151787
Xylometazoline, also spelled xylomethazoline, is a medication which is used to improve symptoms of nasal congestion, allergic rhinitis, and sinusitis. Xylometazoline was patented in 1956 and came into medical use in 1959. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. 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. 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).
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15324890 |
91.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Otrivin Approved UseXylometazoline is indicated for the temporary relief of nasal congestion due to colds , sinusitis, hay fever , other upper respiratory allergies (allergic rhinitis) and for headache, tubal block, and serious otitis media associated with nasal congestion. |
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Primary | Otrivin Approved UseXylometazoline is indicated for the temporary relief of nasal congestion due to colds , sinusitis, hay fever , other upper respiratory allergies (allergic rhinitis) and for headache, tubal block, and serious otitis media associated with nasal congestion. |
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Primary | Otrivin Approved UseXylometazoline is indicated for the temporary relief of nasal congestion due to colds , sinusitis, hay fever , other upper respiratory allergies (allergic rhinitis) and for headache, tubal block, and serious otitis media associated with nasal congestion. |
PubMed
Title | Date | PubMed |
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The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats. | 1978 Sep-Oct |
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Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats. | 1978 Sep-Oct |
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Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes. | 1994 Nov |
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Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion. | 2001 Nov |
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Nasal mucociliary transport: new evidence for a key role of ciliary beat frequency. | 2002 Mar |
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Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs. | 2003 Feb |
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[Tolerance and effectiveness of oxymetazoline and xylometazoline in treatment of acute rhinitis]. | 2003 Oct |
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Immediate effect of benzalkonium chloride in decongestant nasal spray on the human nasal mucosal temperature. | 2004 Aug |
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Evaluation of protective and therapeutic effects of dexpanthenol on nasal decongestants and preservatives: results of cytotoxic studies in vitro. | 2004 Sep-Oct |
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Decongestant effects of nasal xylometazoline and mometasone furoate in persistent allergic rhinitis. | 2005 Dec |
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[Ultrastructural changes in human nasal mucosa in rhinitis medicamentosa]. | 2006 Oct |
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Immunology and homeopathy. 4. Clinical studies-part 1. | 2006 Sep |
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Efficacy and safety of topical combinations of ipratropium and xylometazoline for the treatment of symptoms of runny nose and nasal congestion associated with acute upper respiratory tract infection. | 2007 Jan-Feb |
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Oxymetazoline plus dexpanthenol in nasal congestion. | 2008 Dec |
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[The influence of different alpha-sympathomimetic drugs and benzalkoniumchlorid on the ciliary beat frequency of in vitro cultured human nasal mucosa cells]. | 2008 Jan |
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The value of herbal medicines in the treatment of acute non-purulent rhinosinusitis. Results of a double-blind, randomised, controlled trial. | 2008 Nov |
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Drug use in children: cohort study in three European countries. | 2008 Nov 24 |
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Xylometazoline hydrochloride 0.1 per cent versus physiological saline in nasal surgical aftercare: a randomised, single-blinded, comparative clinical trial. | 2009 Jan |
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Central serous chorioretinopathy after dacryocystorhinostomy operation on the same side. | 2009 Jan-Feb |
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Relation of nasal air flow to nasal cavity dimensions. | 2009 Jun |
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Effects of topical drops and sprays on mucociliary transport time and nasal air flow. | 2009 Nov |
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Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses. | 2010 |
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Effects of intranasal xylometazoline, alone or in combination with ipratropium, in patients with common cold. | 2010 Apr |
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Treatment of congestion in upper respiratory diseases. | 2010 Apr 8 |
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Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. | 2010 Dec |
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Influence of intranasal sterile isotonic sea water applications on xylometazoline administration: an experimental study in pigs. | 2010 Feb |
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Retrograde intubation in a case of ankylosing spondylitis posted for correction of deformity of spine. | 2010 Jan |
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Comments on: Central serous chorioretinopathy after dacryocystorhinostomy operation on the same side. | 2010 Mar-Apr |
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A randomized trial of topical anesthesia comparing lidocaine versus lidocaine plus xylometazoline for unsedated transnasal upper gastrointestinal endoscopy. | 2010 May |
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Prognostic value of anterior rhinomanometry in diode laser turbinoplasty. | 2010 Oct |
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Xylometazoline pretreatment reduces nasotracheal intubation-related epistaxis in paediatric dental surgery. | 2010 Oct |
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Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
Usual adult and adolescent dose Intranasal, 1 to 3 drops or sprays of a 0.1% solution into each nostril every eight to ten hours as needed. Maxiumum of 3 doses per day.
Usual pediatric dose: Intranasal, 1 to 2 sprays of a 0.05% solution into in each nostril every 8 to 10 hours not to exceed 3 doses daily. Do not use for more than 3 days.
Route of Administration:
Nasal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2568628
Agarose plates, containing the Xylometazoline (2.5-200mg/l), were prepared with six series of three wells in each. The addition of the Xylometazoline did not change the pH of the agarose. The leucocytes (107/ml) were preincubated for 30 min. with the Xylometazoline in Parker’s 199 medium and then adjusted to a final concentration of 10’ leucocytes/ml and added to the middle wells. The inner wells were tilled with tissue culture medium and the outer wells with a chemotactically active E. coli culture supernatant. Incubation was carried out for 3 hr in humidified air with 10% CO, or in ordinary air. After fixation the directed migration was measured, i.e. the enlarged projection of distances of migration from the middle wells towards the outer wells.
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WHO-VATC |
QS01GA03
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NCI_THESAURUS |
C29578
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WHO-ESSENTIAL MEDICINES LIST |
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R01AB06
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NCI_THESAURUS |
C29709
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208-390-6
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XYLOMETAZOLINE
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)