You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:11 UTC
HMDB IDHMDB0015070
Secondary Accession Numbers
  • HMDB15070
Metabolite Identification
Common NameOxymetazoline
DescriptionOxymetazoline is only found in individuals that have used or taken this drug. It is a direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)Oxymetazoline is a direct acting sympathomimetic amine, which acts on alpha-adrenergic receptors in the arterioles of the conjunctiva and nasal mucosa. It produces vasoconstriction, resulting in decreased conjunctival congestion in ophthalmic. In nasal it produces constriction, resulting in decreased blood flow and decreased nasal congestion.
Structure
Thumb
Synonyms
ValueSource
2-(4-Tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazolineChEBI
3-[(4,5-dihydro-1H-Imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenolChEBI
6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolChEBI
6-Tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolChEBI
OxymetazolinaChEBI
OxymetazolinumChEBI
OximetazolinumHMDB
Oxymetazoline hydrochloride crystallineHMDB
OxymethazolineHMDB
OxymetozolineHMDB
Hydrochloride, oxymetazolineMeSH
Oxymetazoline hydrochlorideMeSH
Chemical FormulaC16H24N2O
Average Molecular Weight260.3746
Monoisotopic Molecular Weight260.1888634
IUPAC Name6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
Traditional Nameoxymetazoline
CAS Registry Number1491-59-4
SMILES
CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C
InChI Identifier
InChI=1S/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)
InChI KeyWYWIFABBXFUGLM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as xylenols. These are aromatic compounds that contain a xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups, and at least one hydroxyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassXylenes
Direct ParentXylenols
Alternative Parents
Substituents
  • Xylenol
  • Phenylpropane
  • M-xylene
  • O-cresol
  • P-cresol
  • Phenol
  • 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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen 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 Point182 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.052 g/LNot Available
LogP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP3.7ALOGPS
logP3.03ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)10.91ChemAxon
pKa (Strongest Basic)10.15ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.8 m³·mol⁻¹ChemAxon
Polarizability30.64 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004m-3970000000-ee2ec321a55bc78173e1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01di-9847000000-0444f6bbf25ec5a41405View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-c488f3b0f9552a4b7dfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1290000000-a18cdab404c55b4e4497View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-7960000000-1c8f2a11df7638b325dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0090000000-fd2fa239fe46b8ca41c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1090000000-0e91b1578606ee50752fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01r6-4890000000-3e6c50f85057e4ad43d2View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00935 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00935 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00935
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4475
KEGG Compound IDC07363
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxymetazoline
METLIN IDNot Available
PubChem Compound4636
PDB IDNot Available
ChEBI ID7862
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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. MacKinnon AC, Kilpatrick AT, Kenny BA, Spedding M, Brown CM: [3H]-RS-15385-197, a selective and high affinity radioligand for alpha 2-adrenoceptors: implications for receptor classification. Br J Pharmacol. 1992 Aug;106(4):1011-8. [PubMed:1327384 ]
  2. Mitrani P, Srinivasan M, Dodds C, Patel MS: Role of the autonomic nervous system in the development of hyperinsulinemia by high-carbohydrate formula feeding to neonatal rats. Am J Physiol Endocrinol Metab. 2007 Apr;292(4):E1069-78. Epub 2006 Dec 12. [PubMed:17164433 ]
  3. Lepretre N, Mironneau J: Alpha 2-adrenoceptors activate dihydropyridine-sensitive calcium channels via Gi-proteins and protein kinase C in rat portal vein myocytes. Pflugers Arch. 1994 Dec;429(2):253-61. [PubMed:7892112 ]
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. Deplanne V, Galzin AM: Functional characterization of alpha-1-adrenoceptor subtypes in the prostatic urethra and trigone of male rabbit. J Pharmacol Exp Ther. 1996 Aug;278(2):527-34. [PubMed:8768700 ]
  3. Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [PubMed:11774707 ]
  4. Furukawa K, Rosario DJ, Smith DJ, Chapple CR, Uchiyama T, Chess-Williams R: Alpha 1A-adrenoceptor-mediated contractile responses of the human vas deferens. Br J Pharmacol. 1995 Sep;116(1):1605-10. [PubMed:8564226 ]
  5. Gonzalez-Espinosa C, Romero-Avila MT, Mora-Rodriguez DM, Gonzalez-Espinosa D, Garcia-Sainz JA: Molecular cloning and functional expression of the guinea pig alpha(1a)-adrenoceptor. Eur J Pharmacol. 2001 Aug 31;426(3):147-55. [PubMed:11527538 ]