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Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N2
Molecular Weight 244.3758
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XYLOMETAZOLINE

SMILES

Cc1cc(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)

HIDE SMILES / InChI

Description
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).

Originator

Sources: Archiv fuer Experimentelle Pathologie und Pharmakologie Volume 196, Pages 408-30,

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
91.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Otrivin

Approved Use

Xylometazoline 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.
Primary
Otrivin

Approved Use

Xylometazoline 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.
Primary
Otrivin

Approved Use

Xylometazoline 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.
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The influence of alpha-adrenergic drugs on catalepsy induced by haloperidol or fluphenazine in rats.
1978 Sep-Oct
Central action of narcotic analgesics. Part IV. Noradrenergic influences on the activity of analgesics in rats.
1978 Sep-Oct
Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
1994 Nov
Decongestant effects of nasal xylometazoline and mometasone furoate in persistent allergic rhinitis.
2005 Dec
Hospital-acquired sinusitis is a common cause of fever of unknown origin in orotracheally intubated critically ill patients.
2005 Oct 5
Comparison of decongestive capacity of xylometazoline and pseudoephedrine with rhinomanometry and MRI.
2005 Sep
Prevention of nosocomial maxillary sinusitis in the ICU: the effects of topically applied alpha-adrenergic agonists and corticosteroids.
2006 Apr
Radiofrequency for inferior turbinate hypertrophy: could its long-term effect be predicted with a preoperative topical vasoconstrictor drop test?
2006 Jan-Feb
[Ultrastructural changes in human nasal mucosa in rhinitis medicamentosa].
2006 Oct
Immunology and homeopathy. 4. Clinical studies-part 1.
2006 Sep
Effects on nasal nitric oxide production of 2 mechanisms of vasoconstriction.
2007
A case series of xylometazoline overdose in children.
2007
Comparison of optical rhinometry and active anterior rhinomanometry using nasal provocation testing.
2007 Apr
Optical rhinometry: application on children and adolescents for nasal provocation tests.
2007 Aug
Negative pressure pulmonary oedema.
2007 Dec
Trapping of adrenergic decongestant drugs into cellular endomembrane compartments: toxicological and pharmacological consequences.
2007 Dec 20
Diurnal variation of prescribing pattern of primary care doctors in Bahrain.
2007 Feb
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
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
Drug management in chronic rhinosinusitis: identification of the needs.
2007 Mar
Effects of an external nasal dilator strip (ENDS) compared to xylometazolin nasal spray.
2007 Nov
Oxymetazoline plus dexpanthenol in nasal congestion.
2008 Dec
Misuse of xylometazoline nasal drops by inhalation.
2008 Dec
Does nasal decongestion improve obstructive sleep apnea?
2008 Dec
[The influence of different alpha-sympathomimetic drugs and benzalkoniumchlorid on the ciliary beat frequency of in vitro cultured human nasal mucosa cells].
2008 Jan
Sinusitis (acute).
2008 Mar 10
The value of herbal medicines in the treatment of acute non-purulent rhinosinusitis. Results of a double-blind, randomised, controlled trial.
2008 Nov
Drug use in children: cohort study in three European countries.
2008 Nov 24
Miscellaneous.
2008 Oct
The nasal decongestant effect of xylometazoline in the common cold.
2008 Sep-Oct
[Misuse of substances theoretically without abuse potential--case series].
2009
Efficacy and safety of intranasal xylometazoline and ipratropium in patients with common cold.
2009 Apr
OTC use of a topical nasal spray solution containing xylometazoline plus ipratropium in patients with common cold.
2009 Dec
Anaesthetic consideration in macroglossia due to lymphangioma of tongue: a case report.
2009 Feb
Xylometazoline hydrochloride 0.1 per cent versus physiological saline in nasal surgical aftercare: a randomised, single-blinded, comparative clinical trial.
2009 Jan
Central serous chorioretinopathy after dacryocystorhinostomy operation on the same side.
2009 Jan-Feb
A comparison of xylometazoline (Otrivine) and phenylephrine/lignocaine mixture (Cophenylcaine) for the purposes of rigid nasendoscopy: a prospective, double-blind, randomised trial.
2009 Jun
Numerical simulation and nasal air-conditioning.
2010
Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses.
2010
Effects of intranasal xylometazoline, alone or in combination with ipratropium, in patients with common cold.
2010 Apr
Treatment of congestion in upper respiratory diseases.
2010 Apr 8
Case report: unilateral mydriasis following nasal cautery.
2010 Dec
Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline.
2010 Dec
Influence of intranasal sterile isotonic sea water applications on xylometazoline administration: an experimental study in pigs.
2010 Feb
Retrograde intubation in a case of ankylosing spondylitis posted for correction of deformity of spine.
2010 Jan
Comments on: Central serous chorioretinopathy after dacryocystorhinostomy operation on the same side.
2010 Mar-Apr
A randomized trial of topical anesthesia comparing lidocaine versus lidocaine plus xylometazoline for unsedated transnasal upper gastrointestinal endoscopy.
2010 May
Prognostic value of anterior rhinomanometry in diode laser turbinoplasty.
2010 Oct
Xylometazoline pretreatment reduces nasotracheal intubation-related epistaxis in paediatric dental surgery.
2010 Oct
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
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.
Name Type Language
XYLOMETAZOLINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
1H-IMIDAZOLE, 2-((4-(1,1-DIMETHYLETHYL)-2,6-DIMETHYLPHENYL)METHYL)-4,5-DIHYDRO-
Systematic Name English
XYLOMETAZOLINE [INN]
Common Name English
XYLOMETAZOLINE [WHO-DD]
Common Name English
2-(4-TERT-BUTYL-2,6-DIMETHYLBENZYL)-2-IMIDAZOLINE
Systematic Name English
XYLOMETAZOLINE [MI]
Common Name English
XYLOMETAZOLINE [VANDF]
Common Name English
BALMINIL
Brand Name English
Classification Tree Code System Code
WHO-VATC QS01GA03
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 28
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-ATC R01AB06
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-ATC R01AA07
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-VATC QR01AB06
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-ATC S01GA53
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-VATC QR01AA07
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-VATC QS01GA53
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
WHO-ATC S01GA03
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
NCI_THESAURUS C29709
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
Code System Code Type Description
IUPHAR
517
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
MESH
C009695
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
DRUG BANK
DB06694
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
NCI_THESAURUS
C87749
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
RXCUI
39841
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
208-390-6
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
WIKIPEDIA
XYLOMETAZOLINE
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
MERCK INDEX
M11554
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY Merck Index
CAS
526-36-3
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
PUBCHEM
5709
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
EVMPD
SUB00122MIG
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
EPA CompTox
526-36-3
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL312448
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
FDA UNII
WPY40FTH8K
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
INN
809
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY
DRUG CENTRAL
3658
Created by admin on Sat Jun 26 11:35:44 UTC 2021 , Edited by admin on Sat Jun 26 11:35:44 UTC 2021
PRIMARY