Identification

Name
Xylometazoline
Accession Number
DB06694
Type
Small Molecule
Groups
Approved, Investigational
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
Product Ingredients
IngredientUNIICASInChI Key
Xylometazoline hydrochlorideX5S84033NZ1218-35-5YGWFCQYETHJKNX-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
4 Way Moisturizing ReliefSpray1 mg/1mLNasalGlaxoSmithKline Consumer Healthcare Holdings (US) LLC2010-01-012017-07-27Us
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 %NasalTeva2007-12-14Not applicableCanada
Balminil Nasal DecongestantSpray0.1 %NasalTeva1997-08-26Not applicableCanada
Certified Decongestant Nasal Spray .1%Solution; Spray0.1 %NasalProdemdis Enr.1996-09-192010-07-15Canada
Cold & Allergy ReliefSpray0.1 %NasalPharmascience Inc2003-02-01Not applicableCanada
Cold & Allergy Relief With MoisturizersSpray0.1 %NasalPharmascience Inc2003-02-01Not applicableCanada
Cold and Allergy Decongestant Nasal SpraySpray0.1 %NasalTeva2011-10-01Not applicableCanada
Decongest NasalSolution0.1 %NasalTeva2007-12-20Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ophtrivin A Ophthalmic DpsXylometazoline hydrochloride (.05 %) + Antazoline sulfate (.5 %)Solution / dropsOphthalmicCiba Vision1992-12-312000-11-08Canada
International/Other Brands
Otriven / Otrivin / Otrivine / Otrix / Xylomet / Xylostar (Intas)
Categories
UNII
WPY40FTH8K
CAS number
526-36-3
Weight
Average: 244.3752
Monoisotopic: 244.193948778
Chemical Formula
C16H24N2
InChI Key
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

Pharmacology

Indication

It is used for treating nasal congestion and minor inflammation due to allergies or colds.

Associated Conditions
Pharmacodynamics

Xylometazoline 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 action

Xylometazoline 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.

TargetActionsOrganism
AAlpha-1A adrenergic receptor
agonist
Human
AAlpha-2A adrenergic receptor
agonist
Human
AAlpha-2B adrenergic receptor
agonist
Human
UAlpha-1B adrenergic receptor
agonist
Human
UAlpha-1D adrenergic receptor
agonist
Human
UAlpha-2C adrenergic receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
MianserinThe therapeutic efficacy of Xylometazoline can be decreased when used in combination with Mianserin.
Food Interactions
Not Available

References

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
Human Metabolome Database
HMDB0015640
KEGG Compound
C07913
PubChem Compound
5709
PubChem Substance
99443248
ChemSpider
5507
BindingDB
30703
ChEBI
10082
ChEMBL
CHEMBL312448
PharmGKB
PA165958368
IUPHAR
517
Guide to Pharmacology
GtP Drug Page
Wikipedia
Xylometazoline
ATC Codes
S01GA53 — Xylometazoline, combinationsR01AB06 — XylometazolineS01GA03 — XylometazolineR01AA07 — Xylometazoline
AHFS Codes
  • 04:00.00 — Antihistamine Drugs
  • 52:32.00 — Vasoconstrictors

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Rhinitis1
4CompletedTreatmentFlexible Nasendoscopy1
4CompletedTreatmentObstructive Sleep Apnea Syndrome (OSAS) / Rhinitis1
Not AvailableCompletedNot AvailableAcute Rhinitis1
Not AvailableCompletedTreatmentBronchiolitis1
Not AvailableNot Yet RecruitingHealth Services ResearchBronchoscopy1
Not AvailableRecruitingDiagnosticNasal Obstruction / Obstructive Sleep Apnea (OSA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SprayNasal1 mg/1mL
SprayNasal10 mg/10mL
SprayNasal.05 mg/10mL
SolutionNasal0.1 %
SprayNasal0.1 %
Solution; sprayNasal0.1 %
Solution; sprayNasal.1 %
SprayNasal.1 %
Solution / dropsNasal0.1 %
Solution / dropsOphthalmic
SprayNasal0.05 %
Solution / dropsNasal0.05 %
Liquid; sprayNasal.1 %
Solution / dropsNasal.05 %
SprayNasal.05 %
SprayNasal.015 mL/15mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)132 °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 RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0090000000-c862fcdd09df2d7e84e1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0090000000-8a168e444e92aebe729e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0190000000-fea379e1a78158c80c57
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0490000000-f84be52191db834c336a
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01s2-1950000000-6ff7d495e9ab66e5291e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01ta-1920000000-4fa30a0ba8151f6081f3

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropanes
Direct Parent
Phenylpropanes
Alternative Parents
m-Xylenes / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Phenylpropane / M-xylene / Xylene / Imidolactam / 2-imidazoline / Amidine / Carboxylic acid amidine / Azacycle / Organoheterocyclic compound / Organic 1,3-dipolar compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
alkylbenzene (CHEBI:10082)

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) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
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 oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
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...
Gene Name
ADRA2B
Uniprot ID
P18089
Uniprot Name
Alpha-2B adrenergic receptor
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) prot...
Gene Name
ADRA1B
Uniprot ID
P35368
Uniprot Name
Alpha-1B adrenergic receptor
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
Uniprot Name
Alpha-1D adrenergic receptor
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
Uniprot Name
Alpha-2C adrenergic receptor
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]

Drug created on April 25, 2010 17:54 / Updated on November 14, 2018 12:54