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)
Molecular Formula | C16H24N2 |
Molecular Weight | 244.3752 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats. | 1978 Sep-Oct |
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Comparison of cefuroxime with or without intranasal fluticasone for the treatment of rhinosinusitis. The CAFFS Trial: a randomized controlled trial. | 2001 Dec 26 |
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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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Comparison of the clinical efficacy of standard and mucoadhesive-based nasal decongestants. | 2002 Jan |
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The effect of topical xylometazoline on the mucosal temperature of the nasal septum. | 2002 Jul-Aug |
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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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[The protective effect of dexpanthenol in nasal sprays. First results of cytotoxic and ciliary-toxic studies in vitro]. | 2003 Mar |
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[The tolerability of nasal drugs with special regard to preservatives and physico-chemical parameters]. | 2003 Nov |
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Hospital-acquired sinusitis is a common cause of fever of unknown origin in orotracheally intubated critically ill patients. | 2005 Oct 5 |
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Comparison of decongestive capacity of xylometazoline and pseudoephedrine with rhinomanometry and MRI. | 2005 Sep |
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Immunology and homeopathy. 4. Clinical studies-part 1. | 2006 Sep |
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Negative pressure pulmonary oedema. | 2007 Dec |
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Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC). | 2007 Feb |
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Oxymetazoline plus dexpanthenol in nasal congestion. | 2008 Dec |
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Does nasal decongestion improve obstructive sleep apnea? | 2008 Dec |
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Sinusitis (acute). | 2008 Mar 10 |
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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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Miscellaneous. | 2008 Oct |
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OTC use of a topical nasal spray solution containing xylometazoline plus ipratropium in patients with common cold. | 2009 Dec |
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Anaesthetic consideration in macroglossia due to lymphangioma of tongue: a case report. | 2009 Feb |
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Numerical simulation and nasal air-conditioning. | 2010 |
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Treatment of congestion in upper respiratory diseases. | 2010 Apr 8 |
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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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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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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.
Substance Class |
Chemical
Created
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Record UNII |
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Record Status |
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C29578
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C29709
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