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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
Structure of XYLOMETAZOLINE

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)

HIDE SMILES / InChI

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

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
Comparison of cefuroxime with or without intranasal fluticasone for the treatment of rhinosinusitis. The CAFFS Trial: a randomized controlled trial.
2001 Dec 26
The effect of intranasal budesonide spray on mucosal blood flow measured with laser Doppler flowmetry.
2001 Mar
Efficacy and safety of an oral formulation of cetirizine and prolonged-release pseudoephedrine versus xylometazoline nasal spray in nasal congestion.
2001 Nov
Decongestant activity of a new formulation of xylometazoline nasal spray: a double-blind, randomized versus placebo and reference drugs controlled, dose-effect study.
2002
The effect of topical xylometazoline on the mucosal temperature of the nasal septum.
2002 Jul-Aug
Nasal mucociliary transport: new evidence for a key role of ciliary beat frequency.
2002 Mar
[Advance in therapy of acute rhinitis--comparison of efficacy and safety of xylometazoline in combination xylometazoline-dexpanthenol in patients with acute rhinitis].
2003 Apr
Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs.
2003 Feb
[The tolerability of nasal drugs with special regard to preservatives and physico-chemical parameters].
2003 Nov
[Pharmacological and clinical evalutation of nasal obstruction: application to xylometazoline].
2006 Jan-Feb
Radiofrequency for inferior turbinate hypertrophy: could its long-term effect be predicted with a preoperative topical vasoconstrictor drop test?
2006 Jan-Feb
Negative pressure pulmonary oedema.
2007 Dec
Medication administered to children from 0 to 7.5 years in the Avon Longitudinal Study of Parents and Children (ALSPAC).
2007 Feb
Drug management in chronic rhinosinusitis: identification of the needs.
2007 Mar
Oxymetazoline plus dexpanthenol in nasal congestion.
2008 Dec
The value of herbal medicines in the treatment of acute non-purulent rhinosinusitis. Results of a double-blind, randomised, controlled trial.
2008 Nov
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
Relation of nasal air flow to nasal cavity dimensions.
2009 Jun
Effects of topical drops and sprays on mucociliary transport time and nasal air flow.
2009 Nov
Numerical simulation and nasal air-conditioning.
2010
Physiology and pathophysiology of respiratory mucosa of the nose and the paranasal sinuses.
2010
Treatment of congestion in upper respiratory diseases.
2010 Apr 8
Comments on: Central serous chorioretinopathy after dacryocystorhinostomy operation on the same side.
2010 Mar-Apr
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:32:20 UTC 2023
Edited
by admin
on Fri Dec 15 15:32:20 UTC 2023
Record UNII
WPY40FTH8K
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 28
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-ATC R01AB06
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-ATC R01AA07
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-VATC QR01AB06
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-ATC S01GA53
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-VATC QR01AA07
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-VATC QS01GA53
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
WHO-ATC S01GA03
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
NCI_THESAURUS C29709
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
Code System Code Type Description
IUPHAR
517
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
MESH
C009695
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
DRUG BANK
DB06694
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
NCI_THESAURUS
C87749
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
SMS_ID
100000079363
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
RXCUI
39841
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
208-390-6
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
WIKIPEDIA
XYLOMETAZOLINE
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
MERCK INDEX
m11554
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY Merck Index
CAS
526-36-3
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
PUBCHEM
5709
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
EVMPD
SUB00122MIG
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
DAILYMED
WPY40FTH8K
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID8046957
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL312448
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
FDA UNII
WPY40FTH8K
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
INN
809
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
DRUG CENTRAL
3658
Created by admin on Fri Dec 15 15:32:20 UTC 2023 , Edited by admin on Fri Dec 15 15:32:20 UTC 2023
PRIMARY
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