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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxymetazoline Hydrochloridespray, metered.5 mg/mLnasalRebel Distributors Corp2008-12-11Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Visine L.R.liquid.25 mg/mLophthalmicJohnson & Johnson Healthcare Products Inc., Division Of Mc Neil Ppc, Inc.2010-04-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mucinex Full Forcesolution.05 g/100mLnasalReckitt Benckiser LLC2011-10-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mucinex Moisture Smartsolution.05 g/100mLnasalReckitt Benckiser LLC2011-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Mucinex Full Forcesolution.05 g/100mLnasalReckitt Benckiser LLC2011-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxymetazoline Hydrochloridespray, metered.2 mg/.4mLnasalDynamic Pharmaceuticals2009-11-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxymetazoline Hydrochloridespray, metered.2 mg/.4mLnasalDynamic Pharmaceuticals2009-11-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxymetazoline Hydrochloridespray, metered.5 mg/mLnasalCadila Healthcare Limited2009-09-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Oxymetazoline Hydrochloridespray, metered.5 mg/mLnasalZydus Pharmaceuticals (USA) Inc.2009-09-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
International Brands
NameCompany
AfrinNot Available
Dristan 12-HourNot Available
Duramist PlusNot Available
Genasal Nasal Spray Up to 12 Hour ReliefNot Available
IliadinNot 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
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Oxymetazoline hydrochloride
Thumb
  • InChI Key: BEEDODBODQVSIM-UHFFFAOYSA-N
  • Monoisotopic Mass: 296.165541139
  • Average Mass: 296.836
DBSALT000821
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
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
  • P-cresol
  • O-cresol
  • Phenol
  • 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
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9761
Blood Brain Barrier-0.5388
Caco-2 permeable-0.567
P-glycoprotein substrateSubstrate0.8858
P-glycoprotein inhibitor INon-inhibitor0.9477
P-glycoprotein inhibitor IINon-inhibitor0.6585
Renal organic cation transporterInhibitor0.6039
CYP450 2C9 substrateNon-substrate0.7585
CYP450 2D6 substrateNon-substrate0.5707
CYP450 3A4 substrateNon-substrate0.5394
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateInhibitor0.8931
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-inhibitor0.854
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.7951
CarcinogenicityNon-carcinogens0.8923
BiodegradationNot ready biodegradable1.0
Rat acute toxicity4.4155 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8402
hERG inhibition (predictor II)Non-inhibitor0.7432
Pharmacoeconomics
Manufacturers
  • Schering plough healthcare products inc
  • Johnson and johnson group consumer companies
Packagers
Dosage forms
FormRouteStrength
Liquidophthalmic.25 mg/mL
Solutionnasal.05 g/100mL
Spray, meterednasal.2 mg/.4mL
Spray, meterednasal.5 mg/mL
Prices
Unit descriptionCostUnit
Oxymetazoline hcl powder84.42USD g
Afrin 0.05% nose spray0.62USD ml
Drixoral cold & allergy tablet sa0.4USD tablet
Afrin no drip sinus pump mist0.38USD ml
Oxymetazoline 0.05% spray0.38USD ml
Anefrin 0.05% nasal spray0.37USD ml
Afrin sinus spray0.33USD ml
Dristan long lasting mist0.32USD ml
Neo-synephrine 12 hour spray0.28USD ml
Visine long lasting eye drops0.27USD ml
12 hour nasal relief spray0.24USD ml
Dristan cold multi-symp tablet0.23USD tablet
Ocuclear eye drops0.23USD ml
CVS Pharmacy nasal spray 0.05%0.22USD ml
No drip 0.05% nasal spray0.13USD ml
Nasal spray 0.05%0.06USD ml
Sinus nasal spray0.06USD ml
Nasal decongestant 0.05% spray0.03USD ml
Pv nasal spray 0.05%0.03USD ml
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 Solubility0.0515 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.8 m3·mol-1ChemAxon
Polarizability30.64 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (10.5 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesR01AA05R01AB07S01GA04
AHFS Codes
  • 52:32.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74.6 KB)
Interactions
Drug Interactions
Drug
AcebutololMay enhance the adverse/toxic effect of other Sympathomimetics.
AminophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ArformoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
armodafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
ArticaineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineAtoMOXetine may enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
CaffeineMay enhance the adverse/toxic effect of other Sympathomimetics.
ChlorphentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
ClenbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
CocaineMay enhance the adverse/toxic effect of other Sympathomimetics.
DexmethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
DextroamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DiethylpropionMay enhance the adverse/toxic effect of other Sympathomimetics.
DihydrocodeineMay enhance the adverse/toxic effect of other Sympathomimetics.
DipivefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DoxapramMay enhance the adverse/toxic effect of other Sympathomimetics.
DronabinolCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
EpinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
FentanylAlpha1-Agonists may decrease the serum concentration of FentaNYL. Specifically, fentanyl nasal spray serum concentrations may decrease and onset of effect may be delayed.
Fluticasone furoateMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IndacaterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IobenguaneMay diminish the therapeutic effect of Iobenguane I 123.
Ipratropium bromideMay enhance the adverse/toxic effect of other Sympathomimetics.
IsomethepteneMay enhance the adverse/toxic effect of other Sympathomimetics.
IsoprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
LabetalolMay enhance the adverse/toxic effect of other Sympathomimetics.
LevonordefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidLinezolid may enhance the hypertensive effect of Sympathomimetics.
LisdexamfetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MephentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
MetaraminolMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethoxamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
ModafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
NabiloneCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhendimetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PheniramineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenmetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylpropanolamineMay enhance the adverse/toxic effect of other Sympathomimetics.
PirbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
PropylhexedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PseudoephedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
RitodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalbutamolMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Tedizolid PhosphateTedizolid may enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TheophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
TriprolidineMay enhance the adverse/toxic effect of other Sympathomimetics.
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