Oxymetazoline

Identification

Summary

Oxymetazoline is an alpha-1A adrenoceptor agonist used to treat nasal congestion, allergic reactions of the eye, and facial erythema associated with rosacea.

Brand Names
Afrin, Dristan 12-hour Nasal Spray, Kovanaze, Nostrilla, Rhofade, Sinex Long-acting, Upneeq, Zicam Sinus Relief
Generic Name
Oxymetazoline
DrugBank Accession Number
DB00935
Background

Oxymetazoline is an imidazole derivative and a potent, direct-acting alpha (α)-adrenergic agonist with affinity to both α1- and α2-adrenoceptors.1 Oxymetazoline is available in various formulations with a wide variety of clinical implications. The topical formulation of the drug is used to treat persistent facial redness in adults.14 As an effective decongestant, oxymetazoline is available in over-the-counter intranasal sprays used to relieve nasal and sinus congestion caused by a wide variety of conditions, such as common cold, hay fever, and upper respiratory allergies.3,17 In dentistry, oxymetazoline and tetracaine combination intranasal spray (Kovanaze) is used for regional anesthesia during dental procedures in children and adults.13 In July 2020, the FDA approved the use of an ophthalmic formulation of oxymetazoline (Upneeq) in adults with acquired blepharoptosis, or ptosis, making it the first FDA-approved medical treatment for this medical condition.12,15

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 260.3746
Monoisotopic: 260.1888634
Chemical Formula
C16H24N2O
Synonyms
  • 2-(4-tert-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoline
  • 3-[(4,5-dihydro-1H-imidazol-2-yl)methyl]-6-(1,1-dimethylethyl)-2,4-dimethylphenol
  • 6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
  • 6-tert-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol
  • Oximetazolinum
  • Oxymetazolina
  • Oxymetazoline
  • Oxymétazoline
  • Oxymetazolinum
  • Oxymethazoline
  • Oxymetozoline

Pharmacology

Indication

Oxymetazoline is indicated for the topical treatment of persistent facial erythema associated with rosacea in adults.14

Ophthalmic oxymetazoline is indicated for the treatment of acquired blepharoptosis in adults.15

When used in combination with tetracaine intranasally, oxymetazoline is indicated for regional anesthesia when performing a restorative procedure on Teeth 4-13 and A-J in adults and children who weigh 40 kg or more.13

Oxymetazoline can be found in over-the-counter nasal products as a nasal decongestant.17

For off-label uses, oxymetazoline has been used during nasal intubation and during ear, nose, and throat surgery to improve visualization of the airway and to minimize post-operative bleeding.1

Pharmacology
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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Oxymetazoline is an adrenergic α1- and α2-agonist and a direct-acting sympathomimetic drug. By stimulating adrenergic receptors, oxymetazoline causes vasoconstriction of dilated arterioles and reduces blood flow.13 In a radioligand competition study, oxymetazoline displayed higher affinity at α1A-adrenoceptors compared to α2B-adrenoceptors, but with higher potency at α2B-adrenoceptors.5 When sprayed intranasally, oxymetazoline relieved relief nasal congestion and improved nasal airflow in patients with acute coryzal rhinitis for up to 12 hours following a single dose.10

An early in vitro study demonstrated oxymetazoline to exert anti-oxidant actions, where it inhibited microsomal lipid peroxidation and mediated hydroxyl radical scavenging activity. This suggests that oxymetazoline has a beneficial effect against oxidants, which play a role in tissue damage in inflammation.11

Mechanism of action

Oxymetazoline binds to α1- and α2-adrenoceptors, which are Gq-protein-coupled receptors that promote vascular smooth muscle contraction by increasing intracellular calcium levels in response to ligand activation.18

Rosacea is a condition characterized by transient and persistent facial erythema. By stimulating α1A-adrenoceptors and causing vasoconstriction, oxymetazoline is believed to diminish the symptoms of erythema.8 In blepharoptosis, it is hypothesized that oxymetazoline works by stimulating α-adrenergic receptors on the Müller muscle that elevates the upper eyelid, causing muscle contraction.9 Oxymetazoline is used in combination with tetracaine for local anesthesia in dentistry. Such combination use adds beneficial effects: the vasoconstrictor counteracts the local anesthetic agent's vasodilatory action, thereby constricting dilated arterioles and reducing blood flow to the application area.2,13 Oxymetazoline relieves nasal congestion by vasoconstricting the respiratory microvasculature, in both resistance and capacitance blood vessels on the human nasal mucosa, leading to decreased nasal mucosal blood flow, edema, and airflow resistance.4,18

TargetActionsOrganism
AAlpha-1A adrenergic receptor
partial agonist
Humans
AAlpha-2A adrenergic receptor
agonist
partial agonist
Humans
AAlpha-2B adrenergic receptor
agonist
Humans
UAlpha-2C adrenergic receptor
agonist
Humans
UAlpha-1B adrenergic receptor
agonist
Humans
UAlpha-1D adrenergic receptor
agonist
Humans
U5-hydroxytryptamine receptor 1A
agonist
Humans
U5-hydroxytryptamine receptor 1B
agonist
Humans
U5-hydroxytryptamine receptor 1D
agonist
Humans
U5-hydroxytryptamine receptor 1C
partial agonist
Rat
Absorption

Imidazole derivatives such as oxymetazoline are readily absorbed across mucosal membranes, especially in children.1 In adult subjects with erythema associated with rosacea, the mean ± standard deviation (SD) Cmax was 60.5 ± 53.9 pg/mL and the AUC from time 0 to 24 hours (AUC0-24hr) was 895 ±798 pg x hr/mL following topical administration of first-dose oxymetazoline. Following once-daily topical applications for 28 days, the mean ± SD Cmax was 66.4 ± 67.1 pg/mL and the AUC0-24hr was 1050 ± 992 pg x hr/mL. Following twice-daily applications for 28 days, the mean ± SD Cmax was 68.8 ± 61.1 pg/mL and the AUC0-24hr was 1530 ± 922 pg x hr/mL.14

Following single-drop ocular administration of oxymetazoline in healthy adult subjects, the mean ± SD Cmax was 30.5 ± 12.7 pg/mL and the area under the concentration-time curve (AUCinf) was 468 ± 214 pg x hr/mL. The median Tmax was 2 hours, ranging from 0.5 to 12 hours.15

Following nasal administration of an 0.6 mL combination product containing tetracaine and oxymetazoline in adult subjects, the maximum concentrations of oxymetazoline were reached within approximately 10 minutes. The mean Cmax was 1.78 ng/mL and the AUC0-inf value was 4.24 ng x h/mL, with a median Tmax of 5 minutes.13

Volume of distribution

There is limited information on the volume of distribution of oxymetazoline.

Protein binding

In vitro, oxymetazoline is 56.7% to 57.5% bound to human plasma proteins.14

Metabolism

In vitro, oxymetazoline was minimally metabolized by human liver enzymes to produce mono-oxygenated and dehydrogenated metabolites. About 95.9% of the total dose of oxymetazoline remained as an unchanged parent compound after a 120-minute incubation with human liver microsomes.14,15 When incubated in rat, rabbit, and human liver post-mitochondrial supernatant fraction from homogenized tissue (S9) fractions, oxymetazoline was more efficiently metabolized by rabbit liver S9 fractions (~65%) than by rat (~20%) or human (~10%) liver S9 fractions. At concentrations (50 μM) at least 130-fold greater than the usual therapeutic intranasal dose (400 nM), CYP2C19 was suggested to be involved in the oxidation of oxymetazoline following intranasal administration; however, metabolites in humans have not been fully characterized up to date and remain speculated based on in vitro studies using rat and rabbit liver S9 fractions and microsomes.6 The O-glucuronide metabolite catalyzed by UGT1A9 has been identified in vitro.7,13

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Route of elimination

While the excretion of oxymetazoline following nasal, topical, or ophthalmic administration of oxymetazoline has not been fully characterized in humans, it is believed that the predominant route of elimination at clinically relevant concentrations of oxymetazoline is renal excretion.13

Half-life

Following ocular administration in healthy adults, the mean terminal half-life was 8.3 hours, ranging from 5.6 to 13.9 hours.15

The terminal half-life of oxymetazoline following nasal administration of the combination product containing tetracaine and oxymetazoline in adult subjects is approximately 5.2 hours.13

Clearance

There is limited information on the clearance rate of oxymetazoline.

Adverse Effects
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Toxicity

In rats, the oral LD50 is 680 ug/kg and the subcutaneous LD50 is 1630 ug/kg. In mice, the oral LD50 is 4700 ug/kg, the intraperitoneal LD50 is 48 mg/kg, and the subcutaneous LD50 is 34 mg/kg.16

Case reports have documented unintended overdose in both children and adults: overdose has led to dizziness, chest pain, headaches, myocardial infarction, stroke, visual disturbances, arrhythmia, hypertension, or hypotension.13 Accidental ingestion of topical solutions of imidazoline derivatives, including oxymetazoline, in children has resulted in serious adverse events requiring hospitalization, such as nausea, vomiting, lethargy, tachycardia, decreased respiration, bradycardia, hypotension, hypertension, sedation, somnolence, mydriasis, stupor, hypothermia, drooling, and coma.14,15 Possible rebound nasal congestion, irritation of nasal mucosa, and adverse systemic effects (particularly in children), including serious cardiovascular adverse events, have been reported with overdosage as well as prolonged or too frequent intranasal use of oxymetazoline.13 Overdose should be responded with close monitoring, supportive care, and symptomatic treatment.13,14,15

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Oxymetazoline can be decreased when used in combination with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Oxymetazoline is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Oxymetazoline is combined with Acemetacin.
AcetyldigitoxinThe therapeutic efficacy of Acetyldigitoxin can be decreased when used in combination with Oxymetazoline.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Oxymetazoline is combined with Acetylsalicylic acid.
AclidiniumThe risk or severity of Tachycardia can be increased when Oxymetazoline is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Adenosine is combined with Oxymetazoline.
AlclofenacThe risk or severity of hypertension can be increased when Oxymetazoline is combined with Alclofenac.
AlfentanilThe risk or severity of hypertension can be increased when Alfentanil is combined with Oxymetazoline.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Oxymetazoline hydrochlorideK89MJ0S5VY2315-02-8BEEDODBODQVSIM-UHFFFAOYSA-N
International/Other Brands
Dristan 12-Hour (Pfizer) / Duramist Plus (Pfeiffer Pharmaceuticals) / Genasal Nasal Spray Up to 12 Hour Relief / Iliadin / Neo-Synephrine 12 Hour Spray / Nezeril / Nostrilla 12 Hour Nasal Decongestant / OcuClear / Vicks Sinex 12 Hour Nasal Spray / Vicks Sinex 12 Hour Ultra Fine Mist for Sinus Relief
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
RhofadeCream1 g/100gTopicalAclaris Therapeutics, Inc.2017-01-18Not applicableUS flag
RhofadeCream1 g/100gTopicalEpi Health, Llc2021-01-18Not applicableUS flag
RhofadeCream10 mg/1gTopicalAllergan, Inc.2017-01-18Not applicableUS flag
UpneeqSolution / drops1 mg/1mLOphthalmicRvl Pharmaceuticals, Inc.2020-08-21Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
12 Hour NasalSpray0.05 g/100mLNasalAltaire Pharmaceuticals Inc.2001-06-012014-02-21US flag
12 Hour NasalSpray0.05 g/100mLNasalSelect Brand Distributors2000-03-012020-04-30US flag
12 Hour NasalSpray0.05 g/100mLNasalHealthlife of Usa2018-01-02Not applicableUS flag
12 Hour NasalSpray.05 g/100mLNasalMeijer Distribution Inc2015-05-062019-08-19US flag
12 Hour Nasal Decongestant Extra MoisturizingLiquid50 mg/100mLNasalWinco Foods Llc2021-03-25Not applicableUS flag
12 Hour Original Nasal DecongestantLiquid50 mg/100mLNasalWinco Foods Llc2021-02-19Not applicableUS flag
12 Hour Original Nasal DecongestantLiquid50 mg/100mLNasalPreferred Pharmaceuticals Inc.2018-01-02Not applicableUS flag
12 Hour Original Nasal DecongestantLiquid50 mg/100mLNasalSheffield Pharmaceuticals LLC2014-05-30Not applicableUS flag
12 Hour Original Nasal DecongestantLiquid50 mg/100mLNasalNavajo Manufacturing Company Inc.2020-12-10Not applicableUS flag
7 Select NasalSpray0.05 g/100mLNasal7-Eleven2014-08-052019-10-23US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
KovanazeOxymetazoline hydrochloride (0.5 mg/1mL) + Tetracaine hydrochloride (30 mg/1mL)SprayNasalSt. Renatus2016-09-01Not applicableUS flag
Mucinex Sinus-Max Pressure, Pain and Cough and Mucinex Sinus-Max Severe Congestion Relief Clear and CoolOxymetazoline hydrochloride (0.05 g/100mL) + Acetaminophen (325 mg/1) + Dextromethorphan hydrobromide monohydrate (10 mg/1) + Guaifenesin (200 mg/1) + Phenylephrine hydrochloride (5 mg/1)Nasal; OralRB Health (US) LLC2020-08-01Not applicableUS flag

Categories

ATC Codes
S01GA04 — OxymetazolineR01AB07 — OxymetazolineR01AA05 — Oxymetazoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Xylenes
Direct Parent
Xylenols
Alternative Parents
Phenylpropanes / m-Xylenes / Para cresols / Ortho cresols / Imidolactams / Imidazolines / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Azacyclic compounds
show 3 more
Substituents
2-imidazoline / Amidine / Aromatic heteromonocyclic compound / Azacycle / Carboximidamide / Carboxylic acid amidine / Hydrocarbon derivative / Imidolactam / M-xylene / O-cresol
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
phenols, carboxamidine, imidazolines (CHEBI:7862)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
8VLN5B44ZY
CAS number
1491-59-4
InChI Key
WYWIFABBXFUGLM-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-yl)methyl]-2,4-dimethylphenol
SMILES
CC1=CC(=C(O)C(C)=C1CC1=NCCN1)C(C)(C)C

References

General References
  1. Tobias JD, Cartabuke R, Taghon T: Oxymetazoline (Afrin(R)): maybe there is more that we need to know. Paediatr Anaesth. 2014 Aug;24(8):795-8. doi: 10.1111/pan.12399. [Article]
  2. Sisk AL: Vasoconstrictors in local anesthesia for dentistry. Anesth Prog. 1992;39(6):187-93. [Article]
  3. Watanabe H, Foo TH, Djazaeri B, Duncombe P, Mackay IS, Durham SR: Oxymetazoline nasal spray three times daily for four weeks in normal subjects is not associated with rebound congestion or tachyphylaxis. Rhinology. 2003 Sep;41(3):167-74. [Article]
  4. Bende M, Loth S: Vascular effects of topical oxymetazoline on human nasal mucosa. J Laryngol Otol. 1986 Mar;100(3):285-8. doi: 10.1017/s0022215100099151. [Article]
  5. 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. [Article]
  6. Mahajan MK, Uttamsingh V, Daniels JS, Gan LS, LeDuc BW, Williams DA: In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite. Drug Metab Dispos. 2011 Apr;39(4):693-702. doi: 10.1124/dmd.110.036004. Epub 2010 Dec 21. [Article]
  7. Mahajan MK, Uttamsingh V, Gan LS, Leduc B, Williams DA: Identification and characterization of oxymetazoline glucuronidation in human liver microsomes: evidence for the involvement of UGT1A9. J Pharm Sci. 2011 Feb;100(2):784-93. doi: 10.1002/jps.22303. [Article]
  8. Patel NU, Shukla S, Zaki J, Feldman SR: Oxymetazoline hydrochloride cream for facial erythema associated with rosacea. Expert Rev Clin Pharmacol. 2017 Oct;10(10):1049-1054. doi: 10.1080/17512433.2017.1370370. Epub 2017 Aug 24. [Article]
  9. Slonim CB, Foster S, Jaros M, Kannarr SR, Korenfeld MS, Smyth-Medina R, Wirta DL: Association of Oxymetazoline Hydrochloride, 0.1%, Solution Administration With Visual Field in Acquired Ptosis: A Pooled Analysis of 2 Randomized Clinical Trials. JAMA Ophthalmol. 2020 Oct 1. pii: 2771169. doi: 10.1001/jamaophthalmol.2020.3812. [Article]
  10. Druce HM, Ramsey DL, Karnati S, Carr AN: Topical nasal decongestant oxymetazoline (0.05%) provides relief of nasal symptoms for 12 hours. Rhinology. 2018 Dec 1;56(4):343-350. doi: 10.4193/Rhin17.150. [Article]
  11. Westerveld GJ, Scheeren RA, Dekker I, Griffioen DH, Voss HP, Bast A: Anti-oxidant actions of oxymethazoline and xylomethazoline. Eur J Pharmacol. 1995 Sep 15;291(1):27-31. doi: 10.1016/0922-4106(95)90185-x. [Article]
  12. Drugs.com: FDA Approves Upneeq [Link]
  13. FDA Approved Drug Products: KOVANAZE (tetracaine HCl and oxymetazoline HCl) Nasal Spray [Link]
  14. FDA Approved Drug Products: RHOFADE (oxymetazoline hydrochloride) cream, for topical use [Link]
  15. FDA Approved Drug Products: UPNEEQ (oxymetazoline hydrochloride ophthalmic solution), 0.1%, for topical ophthalmic use [Link]
  16. Cayman Chemical: Oxymetazoline Safety Data Sheet [Link]
  17. DailyMed Label: AFRIN NO DRIP ORIGINAL PUMP MIST- oxymetazoline hydrochloride spray, metered [Link]
  18. StatPearls: Alpha 1 Receptor Agonists [Link]
Human Metabolome Database
HMDB0015070
KEGG Drug
D08322
KEGG Compound
C07363
PubChem Compound
4636
PubChem Substance
46505622
ChemSpider
4475
BindingDB
30712
RxNav
7812
ChEBI
7862
ChEMBL
CHEMBL762
ZINC
ZINC000000057435
Therapeutic Targets Database
DAP000235
PharmGKB
PA164748840
Guide to Pharmacology
GtP Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxymetazoline
MSDS
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherHealthy Controls / Major Depressive Disorder (MDD)1
4CompletedPreventionThroat Disorder1
4CompletedTreatmentAcne Rosacea1
4CompletedTreatmentAdenoidal Hypertrophy1
4CompletedTreatmentAllergic Rhinitis (AR)1
4CompletedTreatmentAllergic Rhinitis (AR) / Rhinitis Medicamentosa / Tachyphylaxis1
4CompletedTreatmentCitalopram / Major Depressive Disorder (MDD)1
4CompletedTreatmentDepression / Suicidal Thoughts1
4CompletedTreatmentEndoscopic Sinus Surgery / Polyps, Nasal1
4CompletedTreatmentNasal Obstruction Present Finding1

Pharmacoeconomics

Manufacturers
  • Schering plough healthcare products inc
  • Johnson and johnson group consumer companies
Packagers
  • Altaire Pharmaceuticals
  • Bayer Healthcare
  • Chain Drug
  • CVS Pharmacy
  • Palmetto Pharmaceuticals Inc.
  • Perrigo Co.
  • Pfizer Inc.
  • S&P Healthcare
  • Spectrum Pharmaceuticals
  • Target Corp.
  • Walgreen Co.
  • Wyeth Pharmaceuticals
Dosage Forms
FormRouteStrength
SolutionNasal0.025 %
SprayTopical0.05 g/100mL
SprayNasal0.5 g/100mL
SolutionNasal; Respiratory (inhalation)0.25 mg
SprayNasal0.05 mg / mL
Spray, meteredNasal0.5 g/1mL
Spray, meteredNasal0.05 g/100mL
Spray, meteredNasal0.05 mg/1mL
LiquidNasal0.5 mg/1mL
SolutionIntrasinal; Nasal0.25 mg
SolutionIntrasinal; Nasal0.5 mg
SprayNasal0.05 mg/100mL
SprayNasal0.2 mg/0.4mL
SprayNasal0.05 g/1mL
SolutionConjunctival; Ophthalmic0.25 mg
SprayNasal0.5 %
SprayNasal0.00050 g/1mL
Spray, meteredNasal0.05 % w/v
Solution / dropsNasal0.025 %
Solution / dropsNasal; Topical
SprayNasal
SprayNasal0.05 mg/100mg
LiquidNasal0.05 %
SolutionNasal0.05 % w/v
LiquidNasal50 mg/100mL
SolutionNasal0.05 g/100mL
SprayNasal0.05 % w/v
SolutionNasal0.05 mg/100mL
Solution / drops; sprayNasal.025 %
KitTopical0.05 g/100mL
SprayNasal5 g/100mL
Solution / dropsNasal0.05 g/100mL
LiquidTopical0.05 g/100mL
Solution / dropsNasal
SprayNasal
Solution / drops; suspension / dropsNasal
SprayNasal; Topical
SolutionIntrasinal; Nasal0.1 mg
LiquidNasal0.05 g/100mL
LiquidNasal50 mg/1mL
SprayNasal0.05 mg/1mL
Spray, meteredNasal0.0005 mL/100mL
Spray, meteredNasal0.05 mg/100mL
Solution / dropsOphthalmic.25 mg / mL
SolutionIntrasinal; Nasal50 mg
SuspensionIntrasinal; Nasal25 mg
SolutionNasal; Respiratory (inhalation)0.025 g
Spray, meteredNasal0.05 %
SolutionNasal; Respiratory (inhalation)50 mg
SolutionOral25 mg
Solution / dropsOphthalmic
SolutionNasal; Respiratory (inhalation)0.5 mg
SolutionNasal; Oral0.026 g
SolutionIntraocular; Ophthalmic0.25 mg
SprayOral0.5 mg/1mL
Spray, meteredNasal0.2 mg/0.4mL
Spray, meteredNasal0.5 mg/1mL
SprayNasal0.05 mg/1
SprayNasal0.01 %
SprayNasal0.05 %
SprayNasal50.0 mg/100.0mL
SprayNasal50 mg/100mL
JellyNasal0.05 {VP}/100{VP}
CreamTopical1 g/100g
CreamTopical10 mg/1g
SolutionNasal0.05 % w/w
LiquidNasal0.05 g/15mL
SprayNasal7.5 mg/15mL
SprayNasal0.5 mg/1mL
SprayNasal0.05 g/100mL
Solution / dropsOphthalmic1 mg/1mL
SprayNasal0.512 mg/1mL
SprayNasal0.0005 g/1mL
SprayNasal.05 %
SprayNasal0.0005055 g/1mL
SprayNasal0.0005095 g/1mL
SprayNasal0.000512 g/1mL
LiquidOphthalmic0.25 mg/1mL
LiquidOphthalmic.025 %
Solution / dropsOphthalmic0.025 %
SolutionNasal; Topical
SprayNasal.005 g/100mL
SprayNasal.05 g/100mL
LiquidNasal0.0005 g/1g
SprayNasal.5 mg/1mL
SolutionNasal0.05 %
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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8580282No2013-11-122030-04-02US flag
US6413499No2002-07-022020-03-20US flag
US9308191No2016-04-122030-04-02US flag
US8883838No2014-11-112031-12-01US flag
US7812049No2010-10-122028-05-02US flag
US8420688No2013-04-162024-08-02US flag
US9974773No2018-05-222035-06-11US flag
US8815929No2014-08-262024-01-22US flag
US10335391No2019-07-022035-06-11US flag
US8357714No2011-08-262031-08-26US flag
US9867808No2011-08-262031-08-26US flag
US10751325No2015-06-112035-06-11US flag
US10799481No2019-12-162039-12-16US flag
US10912765No2011-08-262031-08-26US flag
US10814001No2019-12-162039-12-16US flag
US10898573No2019-12-162039-12-16US flag
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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)182 °CPhysProp
logP3.4Not Available
Predicted Properties
PropertyValueSource
logP3.03ChemAxon
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (10.5 KB)
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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Partial 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. [Article]
  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. [Article]
  3. Shibata K, Taketani K: [Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. Fukuoka Igaku Zasshi. 2001 Nov;92(11):377-83. [Article]
  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. [Article]
  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. [Article]
  6. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
Partial 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. 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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. 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. [Article]
  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. [Article]
  3. 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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Schoeffter P, Hoyer D: Interaction of the alpha-adrenoceptor agonist oxymetazoline with serotonin 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D receptors. Eur J Pharmacol. 1991 Apr 17;196(2):213-6. doi: 10.1016/0014-2999(91)90432-p. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Schoeffter P, Hoyer D: Interaction of the alpha-adrenoceptor agonist oxymetazoline with serotonin 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D receptors. Eur J Pharmacol. 1991 Apr 17;196(2):213-6. doi: 10.1016/0014-2999(91)90432-p. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1D
Uniprot ID
P28221
Uniprot Name
5-hydroxytryptamine receptor 1D
Molecular Weight
41906.38 Da
References
  1. Schoeffter P, Hoyer D: Interaction of the alpha-adrenoceptor agonist oxymetazoline with serotonin 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D receptors. Eur J Pharmacol. 1991 Apr 17;196(2):213-6. doi: 10.1016/0014-2999(91)90432-p. [Article]
Kind
Protein
Organism
Rat
Pharmacological action
Unknown
Actions
Partial agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
Htr2c
Uniprot ID
P08909
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51916.005 Da
References
  1. Schoeffter P, Hoyer D: Interaction of the alpha-adrenoceptor agonist oxymetazoline with serotonin 5-HT1A, 5-HT1B, 5-HT1C and 5-HT1D receptors. Eur J Pharmacol. 1991 Apr 17;196(2):213-6. doi: 10.1016/0014-2999(91)90432-p. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Mahajan MK, Uttamsingh V, Gan LS, Leduc B, Williams DA: Identification and characterization of oxymetazoline glucuronidation in human liver microsomes: evidence for the involvement of UGT1A9. J Pharm Sci. 2011 Feb;100(2):784-93. doi: 10.1002/jps.22303. [Article]
  2. FDA Approved Drug Products: KOVANAZE (tetracaine HCl and oxymetazoline HCl) Nasal Spray [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Curator comments
At concentrations (50 μM) at least 130-fold greater than the usual therapeutic intranasal dose (400 nM), oxymetazoline underwent oxidation mediated by CYP2C19 (Mahajan et al., 2011).
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Mahajan MK, Uttamsingh V, Daniels JS, Gan LS, LeDuc BW, Williams DA: In vitro metabolism of oxymetazoline: evidence for bioactivation to a reactive metabolite. Drug Metab Dispos. 2011 Apr;39(4):693-702. doi: 10.1124/dmd.110.036004. Epub 2010 Dec 21. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 24, 2021 14:58