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Identification
NameXylometazoline
Accession NumberDB06694
TypeSmall Molecule
GroupsApproved
Description

A nasal vasoconstricting decongestant drug which acts by binding to the same receptors as adrenaline. It is applied as a spray or as drops into the nose to ease inflammation and congestion of the nasal passageways. It binds alpha-adrenergic receptors to activate the adrenal system which causes systemic vasoconstriction, thereby easing nasal congestion.

Structure
Thumb
Synonyms
Balminil
Xylomethazoline
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
4 Way Moisturizing Reliefspray.01 L/LnasalNovartis Consumer Health, Inc.2010-01-01Not applicableUs
Aqua Maris Fast Acting Decongestantspray10 mg/10mLnasalJgl North America Llc2012-12-15Not applicableUs
Aqua Maris Kids Fast Acting Decongestantspray.05 mg/10mLnasalJgl North America Llc2010-09-27Not applicableUs
Balminil Decongestsolution0.1 %nasalTeva Canada Limited2007-12-14Not applicableCanada
Balminil Nasal Decongestantspray0.1 %nasalTeva Canada Limited1997-08-26Not applicableCanada
Certified Decongestant Nasal Spray .1%solution; spray0.1 %nasalProdemdis Enr.1996-09-192010-07-15Canada
Cold and Allergy Decongestant Nasal Sprayspray0.1 %nasalTeva Canada Limited2011-10-01Not applicableCanada
Decongest Nasalsolution0.1 %nasalTeva Canada Limited2007-12-20Not applicableCanada
Decongestant Nasal Sprayspray0.1 %nasalCrlsNot applicableNot applicableCanada
Decongestant Nasal Sprayspray0.1 %nasalJamp Pharma Corporation2005-01-31Not applicableCanada
Decongestant Nasal Sprayspray0.1 %nasalPharmascience Inc2003-02-01Not applicableCanada
Decongestant Nasal Spray - 0.10%liquid; spray.1 %nasalWes Pak Products Ltd.1998-01-142000-08-04Canada
Decongestant Nasal Spray 0.1%spray.1 %nasalTeva Canada Limited1993-12-31Not applicableCanada
Decongestant Nasal Spray 0.1%solution; spray.1 %nasalProdemdis Enr.1996-09-192008-08-08Canada
Decongestant Nasal Spray 0.1% USPspray.1 %nasalKsl Pharmaceuticals1992-12-311996-09-09Canada
Decongestant Nasal Spray 0.1% W/Vspray.1 %nasalStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1993-12-312002-07-31Canada
Decongestant Nasal Spray With Moisturizersspray0.1 %nasalJamp Pharma Corporation2005-01-31Not applicableCanada
Decongestant Nasal Spray With Moisturizersspray0.1 %nasalPharmascience Inc2003-02-01Not applicableCanada
Decongestant Nose Drops 0.1%drops0.1 %nasalLaboratoires Confab Inc1991-12-31Not applicableCanada
Nasal Decongestant Spray With Moisturizersspray0.1 %nasalCrlsNot applicableNot applicableCanada
Nasal Decongestant Spray With Moisturizersliquid0.1 %nasalLaboratoires Confab Inc2000-11-11Not applicableCanada
Otrivin Allergy and Cold Decongestant Nasal Sprayspray0.05 %nasalNovartis Consumer Health Canada Inc.1999-08-09Not applicableCanada
Otrivin Cold and Allergy Decongestant Nose Dropssolution0.1 %nasalNovartis Consumer Health Canada Inc.1960-12-31Not applicableCanada
Otrivin Cold and Allergy Reliefspray0.1 %nasalGlaxosmithkline Consumer Healthcare Inc.1961-12-31Not applicableCanada
Otrivin Cold and Allergy Relief With Moisturizersspray0.1 %nasalGlaxosmithkline Consumer Healthcare Inc.1996-10-15Not applicableCanada
Otrivin Decongestant Nose Drops 0.05%drops0.05 %nasalNovartis Consumer Health Canada Inc.1999-11-122007-03-23Canada
Otrivin Medicated Complete Nasal Carespray0.1 %nasalGlaxosmithkline Consumer Healthcare Inc.2010-08-02Not applicableCanada
Otrivin Menthol - Asp-liq 0.1%liquid; spray.1 %nasalNovartis Consumer Health Canada Inc.1994-12-312009-06-29Canada
Otrivin Pediatric Decongestant Nose Dropsdrops.05 %nasalNovartis Consumer Health Canada Inc.1960-12-312000-01-18Canada
Otrivin Pediatric Nasal Spray 0.05%spray.05 %nasalNovartis Consumer Health Canada Inc.1985-12-311999-07-21Canada
Otrivin Sinus Reliefsolution0.1 %nasalGlaxosmithkline Consumer Healthcare Inc.Not applicableNot applicableCanada
Otrivin With M-D Pumpspray.1 %nasalNovartis Consumer Health Canada Inc.1987-12-312009-06-29Canada
Sinosil Nasal Decongestantspray.015 mL/15mLnasalHerbion Pakistan Pvt Ltd2011-02-09Not applicableUs
Vaporisateur Nasal Decongestionnantsolution0.1 %nasalLaboratoires Confab Inc1991-12-31Not applicableCanada
Unapproved/Other Products Not Available
International Brands
NameCompany
OtrivenNot Available
OtrivinNot Available
OtrivineNot Available
OtrixNot Available
XylometNot Available
XylostarIntas
Brand mixtures
NameLabellerIngredients
Ophtrivin A Ophthalmic DpsCiba Vision Canada Inc
Salts
Name/CASStructureProperties
Xylometazoline hydrochloride
ThumbNot applicableDBSALT001557
Categories
UNIIWPY40FTH8K
CAS number526-36-3
WeightAverage: 244.3752
Monoisotopic: 244.193948778
Chemical FormulaC16H24N2
InChI KeyInChIKey=HUCJFAOMUPXHDK-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole
SMILES
CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Imidolactam
  • 2-imidazoline
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid amidine
  • Amidine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationIt is used for treating nasal congestion and minor inflammation due to allergies or colds.
PharmacodynamicsXylometazoline is a direct acting sympathomimetic adrenergic alpha-agonist used to induce systemic vasoconstriction, thereby decreasing nasal congestion. The sympathomimetic action of xylometazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (8-12 hours) decongesting effect.
Mechanism of actionXylometazoline is a direct acting sympathomimetic drug, which acts on alpha-adrenergic receptors in the arterioles of the nasal mucosa. This activates the adrenal system to yield systemic vasoconstrction. In producing vasoconstriction, the result is a decrease in blood flow in the nasal passages and consequently decreased nasal congestion.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9866
Blood Brain Barrier+0.7293
Caco-2 permeable-0.5133
P-glycoprotein substrateSubstrate0.8254
P-glycoprotein inhibitor INon-inhibitor0.7469
P-glycoprotein inhibitor IINon-inhibitor0.8244
Renal organic cation transporterInhibitor0.6924
CYP450 2C9 substrateNon-substrate0.7815
CYP450 2D6 substrateNon-substrate0.531
CYP450 3A4 substrateNon-substrate0.5755
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9031
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9147
Ames testNon AMES toxic0.8306
CarcinogenicityNon-carcinogens0.9124
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1884 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9218
hERG inhibition (predictor II)Non-inhibitor0.745
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Spraynasal.01 L/L
Spraynasal10 mg/10mL
Spraynasal.05 mg/10mL
Spraynasal0.1 %
Solution; spraynasal0.1 %
Solution; spraynasal.1 %
Spraynasal.1 %
Dropsnasal0.1 %
Liquidnasal0.1 %
Dropsophthalmic
Spraynasal0.05 %
Dropsnasal0.05 %
Liquid; spraynasal.1 %
Dropsnasal.05 %
Spraynasal.05 %
Spraynasal.015 mL/15mL
Solutionnasal0.1 %
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point132 °CPhysProp
logP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00893 mg/mLALOGPS
logP4.68ALOGPS
logP3.78ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.82 m3·mol-1ChemAxon
Polarizability29.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis ReferenceNot Available
General References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
External Links
ATC CodesR01AA07R01AB06S01GA03S01GA53
AHFS Codes
  • 52:32.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular Weight:
51486.005 Da
References
  1. Yang HT, Endoh M: (+/-)-tamsulosin, an alpha 1A-adrenoceptor antagonist, inhibits the positive inotropic effect but not the accumulation of inositol phosphates in rabbit heart. Eur J Pharmacol. 1996 Oct 3;312(3):281-91. [PubMed:8894610 ]
  2. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Thioesterase binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular Weight:
48956.275 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
  2. Petrusewicz J, Kaliszan R: Effect of imidazoline drugs on human blood platelet aggregation. Thromb Haemost. 1985 Dec 17;54(4):784-7. [PubMed:2868542 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Epinephrine binding
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular Weight:
49565.8 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein heterodimerization activity
Specific Function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine (PE)-stimulated ERK signaling in cardiac myocytes.
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular Weight:
56835.375 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Alpha1-adrenergic receptor activity
Specific Function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular Weight:
60462.205 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Protein homodimerization activity
Specific Function:
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name:
ADRA2C
Uniprot ID:
P18825
Molecular Weight:
49521.585 Da
References
  1. Haenisch B, Walstab J, Herberhold S, Bootz F, Tschaikin M, Ramseger R, Bonisch H: Alpha-adrenoceptor agonistic activity of oxymetazoline and xylometazoline. Fundam Clin Pharmacol. 2010 Dec;24(6):729-39. doi: 10.1111/j.1472-8206.2009.00805.x. [PubMed:20030735 ]
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Drug created on April 25, 2010 17:54 / Updated on December 03, 2015 09:51