Details
Stereochemistry | ACHIRAL |
Molecular Formula | C16H24N2.ClH |
Molecular Weight | 280.836 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1=CC(=CC(C)=C1CC2=NCCN2)C(C)(C)C
InChI
InChIKey=YGWFCQYETHJKNX-UHFFFAOYSA-N
InChI=1S/C16H24N2.ClH/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);1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
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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Detection of particles within the nasal airways before and after nasal decongestion. | 2001 Aug |
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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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The effect of intranasal budesonide spray on mucosal blood flow measured with laser Doppler flowmetry. | 2001 Mar |
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The effect of topical xylometazoline on the mucosal temperature of the nasal septum. | 2002 Jul-Aug |
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[Advance in therapy of acute rhinitis--comparison of efficacy and safety of xylometazoline in combination xylometazoline-dexpanthenol in patients with acute rhinitis]. | 2003 Apr |
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[The tolerability of nasal drugs with special regard to preservatives and physico-chemical parameters]. | 2003 Nov |
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The cavernous body of the human efferent tear ducts contributes to regulation of tear outflow. | 2003 Nov |
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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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[Treatment of inflammatory diseases of the upper respiratory tract -- comparison of a homeopathic complex remedy with xylometazoline]. | 2005 Feb |
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The value of Ems Mineral Salts in the treatment of rhinosinusitis in children. Prospective study on the efficacy of mineral salts versus xylometazoline in the topical nasal treatment of children. | 2005 Oct |
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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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Radiofrequency for inferior turbinate hypertrophy: could its long-term effect be predicted with a preoperative topical vasoconstrictor drop test? | 2006 Jan-Feb |
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A case series of xylometazoline overdose in children. | 2007 |
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Comparison of optical rhinometry and active anterior rhinomanometry using nasal provocation testing. | 2007 Apr |
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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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Drug management in chronic rhinosinusitis: identification of the needs. | 2007 Mar |
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Effects of an external nasal dilator strip (ENDS) compared to xylometazolin nasal spray. | 2007 Nov |
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Misuse of xylometazoline nasal drops by inhalation. | 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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Drug use in children: cohort study in three European countries. | 2008 Nov 24 |
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Miscellaneous. | 2008 Oct |
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[Misuse of substances theoretically without abuse potential--case series]. | 2009 |
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Efficacy and safety of intranasal xylometazoline and ipratropium in patients with common cold. | 2009 Apr |
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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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Relation of nasal air flow to nasal cavity dimensions. | 2009 Jun |
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Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses. | 2010 |
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Case report: unilateral mydriasis following nasal cautery. | 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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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
by
admin
on
Edited
Fri Dec 15 15:35:14 GMT 2023
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on
Fri Dec 15 15:35:14 GMT 2023
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Record UNII |
X5S84033NZ
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 341.20
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C29709
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C29578
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C87583
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m11554
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SUB05152MIG
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
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ACTIVE MOIETY |