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Identification
NameOxymetazoline
Accession NumberDB00935  (APRD01158)
Typesmall molecule
Groupsapproved
Description

A direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1251)

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(4-Tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazolineNot AvailableNot Available
3-[(4,5-dihydro-1H-Imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenolNot AvailableNot Available
6-t-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolNot AvailableNot Available
6-Tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolNot AvailableNot Available
OximetazolinumNot AvailableNot Available
OxymetazolinaNot AvailableNot Available
OxymetazolinumNot AvailableNot Available
OxymethazolineNot AvailableNot Available
OxymetozolineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Oxymetazoline hydrochloride
Thumb
  • InChI Key: BEEDODBODQVSIM-UHFFFAOYSA-N
  • Monoisotopic Mass: 296.165541139
  • Average Mass: 296.836
DBSALT000821
Brand names
NameCompany
AfrinNot Available
Dristan 12-HourNot Available
Duramist PlusNot Available
Genasal Nasal Spray Up to 12 Hour ReliefNot Available
IliadinNot Available
Mucinex Full ForceNot Available
Mucinex Moisture SmartNot Available
Neo-Synephrine 12 Hour SprayNot Available
NezerilNot Available
Nostrilla 12 Hour Nasal DecongestantNot Available
OcuClearNot Available
Vicks Sinex 12 Hour Nasal SprayNot Available
Vicks Sinex 12 Hour Ultra Fine Mist for Sinus ReliefNot Available
Visine L.R.Not Available
Brand mixturesNot Available
Categories
CAS number1491-59-4
WeightAverage: 260.3746
Monoisotopic: 260.1888634
Chemical FormulaC16H24N2O
InChI KeyWYWIFABBXFUGLM-UHFFFAOYSA-N
InChI
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)
IUPAC Name
6-tert-butyl-3-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethylphenol
SMILES
CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C
Mass Specshow(10.5 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassPrenol Lipids
SubclassMonoterpenes
Direct parentAromatic Monoterpenes
Alternative parentsCumenes; Ortho Cresols; Para Cresols; Toluenes; Enols; Polyamines; Carboxamidines
Substituentsp-cresol; o-cresol; toluene; phenol derivative; benzene; amidine; polyamine; enol; carboxylic acid amidine; organonitrogen compound
Classification descriptionThis compound belongs to the aromatic monoterpenes. These are monoterpenes containing at least one aromatic ring.
Pharmacology
IndicationFor treatment of nasal congestion and redness associated with minor irritations of the eye
PharmacodynamicsOxymetazoline a adrenergic alpha-agonists, direct acting sympathomimetic used as a vasoconstrictor to relieve nasal congestion The sympathomimetic action of oxymetazoline constricts the smaller arterioles of the nasal passages, producing a prolonged (up to 12 hours), gentle and decongesting effect. Oxymetazoline elicits relief of conjunctival hyperemia by causing vasoconstriction of superficial conjunctival blood vessels. The drug's action has been demonstrated in acute allergic conjunctivitis and in chemical (chloride) conjunctivitis.
Mechanism of actionOxymetazoline 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9761
Blood Brain Barrier - 0.5388
Caco-2 permeable - 0.567
P-glycoprotein substrate Substrate 0.8858
P-glycoprotein inhibitor I Non-inhibitor 0.9477
P-glycoprotein inhibitor II Non-inhibitor 0.6585
Renal organic cation transporter Inhibitor 0.6039
CYP450 2C9 substrate Non-substrate 0.7585
CYP450 2D6 substrate Non-substrate 0.5707
CYP450 3A4 substrate Non-substrate 0.5394
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8931
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.854
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682
Ames test Non AMES toxic 0.7951
Carcinogenicity Non-carcinogens 0.8923
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 4.4155 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8402
hERG inhibition (predictor II) Non-inhibitor 0.7432
Pharmacoeconomics
Manufacturers
  • Schering plough healthcare products inc
  • Johnson and johnson group consumer companies
Packagers
Dosage forms
FormRouteStrength
LiquidNasal
SolutionNasal
SolutionRespiratory (inhalation)
Solution / dropsOphthalmic
SprayNasal
Prices
Unit descriptionCostUnit
Oxymetazoline hcl powder84.42USDg
Afrin 0.05% nose spray0.62USDml
Drixoral cold & allergy tablet sa0.4USDtablet
Afrin no drip sinus pump mist0.38USDml
Oxymetazoline 0.05% spray0.38USDml
Anefrin 0.05% nasal spray0.37USDml
Afrin sinus spray0.33USDml
Dristan long lasting mist0.32USDml
Neo-synephrine 12 hour spray0.28USDml
Visine long lasting eye drops0.27USDml
12 hour nasal relief spray0.24USDml
Dristan cold multi-symp tablet0.23USDtablet
Ocuclear eye drops0.23USDml
CVS Pharmacy nasal spray 0.05%0.22USDml
No drip 0.05% nasal spray0.13USDml
Nasal spray 0.05%0.06USDml
Sinus nasal spray0.06USDml
Nasal decongestant 0.05% spray0.03USDml
Pv nasal spray 0.05%0.03USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point182 °CPhysProp
logP3.4Not Available
Predicted Properties
PropertyValueSource
water solubility5.15e-02 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 area44.62ChemAxon
rotatable bond count3ChemAxon
refractivity79.8ChemAxon
polarizability30.64ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07363
PubChem Compound4636
PubChem Substance46505622
ChemSpider4475
BindingDB50027075
Therapeutic Targets DatabaseDAP000235
PharmGKBPA164748840
IUPHAR124
Guide to Pharmacology124
Drug Product Database2245578
Drugs.comhttp://www.drugs.com/cdi/oxymetazoline-solution.html
WikipediaOxymetazoline
ATC CodesR01AA05R01AB07S01GA04
AHFS Codes
  • 52:32.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(74.6 KB)
Interactions
Drug Interactions
Drug
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Oxymetazoline. Concomitant therapy should be avoided.
Food InteractionsNot Available

Targets

1. Alpha-1A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details

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
  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
  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
  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
  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

2. Alpha-2A adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-2A adrenergic receptor P08913 Details

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
  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
  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

3. Alpha-2C adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Alpha-2C adrenergic receptor P18825 Details

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.×. Pubmed

4. Alpha-2B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Alpha-2B adrenergic receptor P18089 Details

References:

  1. Uhlen S, Wikberg JE: Delineation of rat kidney alpha 2A- and alpha 2B-adrenoceptors with [3H]RX821002 radioligand binding: computer modelling reveals that guanfacine is an alpha 2A-selective compound. Eur J Pharmacol. 1991 Sep 17;202(2):235-43. Pubmed
  2. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. Pubmed

5. Alpha-1B adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Alpha-1B adrenergic receptor P35368 Details

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.×. Pubmed
  2. Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. Pubmed
  3. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. Pubmed

6. Alpha-1D adrenergic receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Alpha-1D adrenergic receptor P25100 Details

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.×. Pubmed
  2. Akinaga J, Lima V, Kiguti LR, Hebeler-Barbosa F, Alcantara-Hernandez R, Garcia-Sainz JA, Pupo AS: Differential phosphorylation, desensitization, and internalization of alpha1A-adrenoceptors activated by norepinephrine and oxymetazoline. Mol Pharmacol. 2013 Apr;83(4):870-81. doi: 10.1124/mol.112.082313. Epub 2013 Jan 30. Pubmed
  3. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP: ChEMBL: a large-scale bioactivity database for drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1100-7. doi: 10.1093/nar/gkr777. Epub 2011 Sep 23. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12