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 |
---|---|---|---|
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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[Pharmacological and clinical evalutation of nasal obstruction: application to xylometazoline]. | 2006 Jan-Feb |
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Immunology and homeopathy. 4. Clinical studies-part 1. | 2006 Sep |
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Effects on nasal nitric oxide production of 2 mechanisms of vasoconstriction. | 2007 |
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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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Optical rhinometry: application on children and adolescents for nasal provocation tests. | 2007 Aug |
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Negative pressure pulmonary oedema. | 2007 Dec |
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Trapping of adrenergic decongestant drugs into cellular endomembrane compartments: toxicological and pharmacological consequences. | 2007 Dec 20 |
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Diurnal variation of prescribing pattern of primary care doctors in Bahrain. | 2007 Feb |
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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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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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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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Oxymetazoline plus dexpanthenol in nasal congestion. | 2008 Dec |
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Misuse of xylometazoline nasal drops by inhalation. | 2008 Dec |
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Does nasal decongestion improve obstructive sleep apnea? | 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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Health-related quality of life in a trial of acupuncture, sham acupuncture and conventional treatment for chronic sinusitis. | 2008 Jun 27 |
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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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The nasal decongestant effect of xylometazoline in the common cold. | 2008 Sep-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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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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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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A comparison of xylometazoline (Otrivine) and phenylephrine/lignocaine mixture (Cophenylcaine) for the purposes of rigid nasendoscopy: a prospective, double-blind, randomised trial. | 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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Parallel functional activity profiling reveals valvulopathogens are potent 5-hydroxytryptamine(2B) receptor agonists: implications for drug safety assessment. | 2009 Oct |
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Numerical simulation and nasal air-conditioning. | 2010 |
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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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Case report: unilateral mydriasis following nasal cautery. | 2010 Dec |
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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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Structural and functional evolution of the trace amine-associated receptors TAAR3, TAAR4 and TAAR5 in primates. | 2010 Jun 15 |
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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.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 16 17:22:48 UTC 2022
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Record UNII |
WPY40FTH8K
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Record Status |
Validated (UNII)
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Record Version |
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QS01GA03
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NCI_THESAURUS |
C29578
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WHO-ESSENTIAL MEDICINES LIST |
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S01GA53
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QR01AA07
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QS01GA53
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S01GA03
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NCI_THESAURUS |
C29709
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517
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C009695
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DB06694
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208-390-6
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XYLOMETAZOLINE
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M11554
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> AGONIST | |||
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TARGET -> AGONIST |
SHORT-ACTING
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TARGET -> AGONIST |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |