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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:58 UTC
HMDB IDHMDB0015640
Secondary Accession Numbers
  • HMDB15640
Metabolite Identification
Common NameXylometazoline
DescriptionXylometazoline, also known as balminil or otrivin mentol, belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Xylometazoline is a very strong basic compound (based on its pKa). Xylometazoline is a direct acting sympathomimetic drug, which acts on alpha-adrenergic receptors in the arterioles of the nasal mucosa. Xylometazoline is a direct acting sympathomimetic adrenergic alpha-agonist used to induce systemic vasoconstriction, thereby decreasing nasal congestion. 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. The sympathomimetic action of xylometazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (8-12 hours) decongesting effect.
Structure
Data?1582753318
Synonyms
ValueSource
BalminilKegg
XylomethazolineHMDB
AmidrinHMDB
DecongestHMDB
GelonasalHMDB
NasenGel ratiopharmHMDB
NasenSpray ratiopharmHMDB
Nasengel alHMDB
RapakoHMDB
2-(4'-Tert-butyl-2',6'-dimethylphenylmethyl)imidazolineHMDB
BalkisHMDB
Chlorohist-laHMDB
NasenTropfen ratiopharmHMDB
Nasenspray alHMDB
Nasentropfen alHMDB
OtrasprayHMDB
Otrivin mentolHMDB
Xylometazoline monohydrochlorideHMDB
Idril NHMDB
NasanHMDB
StasHMDB
IdasalHMDB
ImidinHMDB
NovorinHMDB
OtradropsHMDB
OtrivenHMDB
OtrivinHMDB
SnupHMDB
Espa-rhinHMDB
Schnupfen endrineHMDB
Xylometazoline hydrochlorideHMDB
Chemical FormulaC16H24N2
Average Molecular Weight244.3752
Monoisotopic Molecular Weight244.193948778
IUPAC Name2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole
Traditional Namexylometazoline
CAS Registry Number526-36-3
SMILES
CC1=CC(=CC(C)=C1CC1=NCCN1)C(C)(C)C
InChI Identifier
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)
InChI KeyHUCJFAOMUPXHDK-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • M-xylene
  • Xylene
  • Imidolactam
  • 2-imidazoline
  • Amidine
  • Carboxylic acid amidine
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point131 - 133 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0089 g/LALOGPS
logP4.68ALOGPS
logP3.78ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity77.82 m³·mol⁻¹ChemAxon
Polarizability29.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05r0-3920000000-c6f0d063c06a4d3ad4d3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0090000000-c862fcdd09df2d7e84e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0090000000-8a168e444e92aebe729eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0190000000-fea379e1a78158c80c57Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0490000000-f84be52191db834c336aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01s2-1950000000-6ff7d495e9ab66e5291eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01ta-1920000000-4fa30a0ba8151f6081f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0190000000-060c2ca9dfe2d240b99eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2590000000-a8065812eb0874b9f1afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-6930000000-217f14ab6f9450f30df2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-4562776c5453eb7a749bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1090000000-ca34d5dc761b0014453cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ta-2930000000-18d8456eb2b8ab553c53Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06694 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06694 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06694
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5507
KEGG Compound IDC07913
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkXylometazoline
METLIN IDNot Available
PubChem Compound5709
PDB IDNot Available
ChEBI ID214810
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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 = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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 > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:
ADRA1D
Uniprot ID:
P25100
Molecular weight:
60462.2
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 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
49521.6
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 ]