U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N2O
Molecular Weight 260.3746
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYMETAZOLINE

SMILES

CC1=C(CC2=NCCN2)C(C)=C(O)C(=C1)C(C)(C)C

InChI

InChIKey=WYWIFABBXFUGLM-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C16H24N2O
Molecular Weight 260.3746
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/monograph/oxymetazoline-hydrochloride.html

Oxymetazoline is an adrenergic alpha-agonist, 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. Oxymetazoline is self-medication for temporary relief of nasal congestion associated with the common cold, hay fever, or other upper respiratory allergies. Oxymetazoline is available over-the-counter as a topical decongestant in the form of oxymetazoline hydrochloride in nasal sprays such as Afrin, Operil, Dristan, Dimetapp, oxyspray, Facimin, Nasivin, Nostrilla, Sudafed OM, Vicks Sinex, Zicam, SinuFrin, and Mucinex Full Force. Due to its vasoconstricting properties, oxymetazoline is also used to treat nose bleeds and eye redness.

CNS Activity

Curator's Comment: Oxymetazoline does not cross the blood brain barrier

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Oxymetazoline Hydrochloride

Approved Use

Temporary relief of nasal congestion (due to a cold, hay fever, or other upper respiratory allergies) and sinus congestion/pressure.

Launch Date

1989
Primary
OCUCLEAR

Approved Use

Relief of redness of eye due to minor eye irritations

Launch Date

1986
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60.5 pg/mL
3 mg single, topical
dose: 3 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
OXYMETAZOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.78 ng/mL
0.3 mg single, nasal
dose: 0.3 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: Tetracaine
OXYMETAZOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
895 pg × h/mL
3 mg single, topical
dose: 3 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
OXYMETAZOLINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.24 ng × h/mL
0.3 mg single, nasal
dose: 0.3 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: Tetracaine
OXYMETAZOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.23 h
0.3 mg single, nasal
dose: 0.3 mg
route of administration: Nasal
experiment type: SINGLE
co-administered: Tetracaine
OXYMETAZOLINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.05 % single, intranasal
Dose: 0.05 %
Route: intranasal
Route: single
Dose: 0.05 %
Sources:
unhealthy, 4 years
Health Status: unhealthy
Age Group: 4 years
Sex: M
Sources:
Other AEs: Hypertensive crisis...
Other AEs:
Hypertensive crisis (1 patient)
Sources:
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Disc. AE: Application site dermatitis, Application site erythema...
AEs leading to
discontinuation/dose reduction:
Application site dermatitis (1.4%)
Application site erythema (0.5%)
Application site pain (0.5%)
Application site dryness (0.2%)
Hypoesthesia (0.2%)
Paresthesia (0.2%)
Rash (0.2%)
Urticaria (0.2%)
Photosensitivity reaction (0.2%)
Sources:
1.5 % 2 times / day multiple, topical
Highest studied dose
Dose: 1.5 %, 2 times / day
Route: topical
Route: multiple
Dose: 1.5 %, 2 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertensive crisis 1 patient
0.05 % single, intranasal
Dose: 0.05 %
Route: intranasal
Route: single
Dose: 0.05 %
Sources:
unhealthy, 4 years
Health Status: unhealthy
Age Group: 4 years
Sex: M
Sources:
Application site dryness 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Hypoesthesia 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Paresthesia 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Photosensitivity reaction 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Rash 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Urticaria 0.2%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Application site erythema 0.5%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Application site pain 0.5%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
Application site dermatitis 1.4%
Disc. AE
1 % 1 times / day multiple, topical
Dose: 1 %, 1 times / day
Route: topical
Route: multiple
Dose: 1 %, 1 times / day
Sources:
unhealthy, 53.1 years (range: 19–81 years)
Health Status: unhealthy
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Sources:
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
no (co-administration study)
Comment: concomitant oral moderate CYP2C19 inhibitors (e.g., esomeprazole, fluoxetine, and omeprazole): the results did not indicate an increase in oxymetazoline exposure associated with coadministration of oral moderate CYP2C19 inhibitors
Page: 7.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Vasocontractile effects of alpha 2-adrenergic agonists associated with intracellular calcium release.
2002
Endothelial inhibitory modulation on the contractile responses to alpha 2-adrenergic agonists.
2002
[The relationship between ostial patency and medical treatment in acute maxillary sinusitis: an experimental study].
2002 Jul-Aug
Contractile responses of the rat vas deferens after epithelium removal.
2002 May 3
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Topical nasal anesthesia for transnasal fiberoptic laryngoscopy: a prospective, double-blind, cross-over study.
2003 Apr
Stimulation of interleukin-12 production in mouse macrophages via activation of p38 mitogen-activated protein kinase by alpha2-adrenoceptor agonists.
2003 Apr 25
Pharmacological characterization of alpha 2-adrenoceptor-mediated responses in pig nasal mucosa.
2003 Aug
alpha 2B-Adrenoceptor levels govern agonist and inverse agonist responses in PC12 cells.
2003 Aug 15
Evidence for nonadrenoceptor responses to imidazoline derivatives in the porcine isolated rectal artery.
2003 Dec
Alpha(2A)-adrenergic versus imidazoline receptor controversy in rilmenidine's action: alpha(2A)-antagonism in humans versus alpha(2A)-agonism in rabbits.
2003 Dec
Evidence for the role of alpha1D- and alpha1A-adrenoceptors in contraction of the rat mesenteric artery.
2003 Feb
Transdermal penetration of vasoconstrictors--present understanding and assessment of the human epidermal flux and retention of free bases and ion-pairs.
2003 Feb
5-HT7 receptor-mediated relaxation of the oviduct in nonpregnant proestrus pigs.
2003 Feb 14
Contractile actions of imidazoline alpha-adrenoceptor agonists and effects of noncompetitive alpha1-adrenoceptor antagonists in human vas deferens.
2003 Feb 21
Topical nasal anesthesia and laryngopharyngeal sensory testing: a prospective, double-blind crossover study.
2003 Jan
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens.
2003 Jul
Central serous chorioretinopathy associated with administration of sympathomimetic agents.
2003 Jul
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.
2003 Jul
Alpha 2 adrenoceptor-mediated presynaptic inhibition of primary afferent glutamatergic transmission in rat substantia gelatinosa neurons.
2003 Mar
[The use of oxymetazoline in nasal endoscopic sinus surgery].
2003 May
[Tolerance and effectiveness of oxymetazoline and xylometazoline in treatment of acute rhinitis].
2003 Oct
Oligomerization of the alpha 1a- and alpha 1b-adrenergic receptor subtypes. Potential implications in receptor internalization.
2003 Oct 10
Oxymetazoline nasal spray three times daily for four weeks in normal subjects is not associated with rebound congestion or tachyphylaxis.
2003 Sep
Alpha 2-adrenoceptors in the basal ganglia have a role in memory consolidation and reinforcement.
2003 Sep
Sympathomimetic drug allergy: cross-reactivity study by patch test.
2004
Bulk is a determinant of oxymetazoline affinity for the alpha1A-adrenergic receptor.
2004
Chronic rhinosinusitis: management for optimal outcomes.
2004
Intranasal drug delivery: an alternative to intravenous administration in selected emergency cases.
2004 Apr
Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane.
2004 Aug
Antimuscarinic action of oxymetazoline on human intraocular muscles.
2004 Aug
[Ethyl-3H]RS-79948-197 alpha2-adrenoceptor autoradiography validation in alpha2-adrenoceptor knockout mice.
2004 Aug 30
Behavioral effects of serotonin and serotonin agonists in two crayfish species, Procambarus clarkii and Orconectes rusticus.
2004 Dec
Construction and analytical applications of plastic membrane electrode for oxymetazoline hydrochloride.
2004 Feb
Human alpha1D-adrenoceptor phosphorylation and desensitization.
2004 May 15
The Janus faces of adrenoceptors: factors controlling the coupling of adrenoceptors to multiple signal transduction pathways.
2004 Nov
Thunderclap headache and reversible segmental cerebral vasoconstriction associated with use of oxymetazoline nasal spray.
2004 Sep 14
Use of mometasone furoate aqueous nasal spray in the treatment of rhinitis medicamentosa: an experimental study.
2005 Apr
Pulmonary edema following phenylephrine intranasal spray administration during the induction of general anesthesia in a child.
2005 Apr 30
Oxymetazoline solutions inhibit middle ear pathogens and are not ototoxic.
2005 Aug
Oxymetazoline is equivalent to ciprofloxacin in preventing postoperative otorrhea or tympanostomy tube obstruction.
2005 Feb
Early changes in insulin secretion and action induced by high-fat diet are related to a decreased sympathetic tone.
2005 Jan
An assessment for the presence of bacterial contamination of Venturi principle atomizers in a clinical setting.
2005 Jan-Feb
[Investigation of the effect of oxymetazoline on the duration of rhinitis].
2005 Oct 13
[Investigation of the effect of oxymetazoline on the duration of rhinitis. results of a placebo-controlled double-blind study in patients with acute rhinitis].
2005 Oct 6
[The observation of the ciliotoxicity of nasal mucosa with nasal decongestant].
2005 Sep
Pharmacological characterization of postjunctional alpha-adrenoceptors in human nasal mucosa.
2005 Sep-Oct
Oxymetazoline inhibits proinflammatory reactions: effect on arachidonic acid-derived metabolites.
2006 Feb
Nasal wall compliance in vasomotor rhinitis.
2006 Jan
Human breast cell lines exhibit functional alpha2-adrenoceptors.
2006 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Ophthalmic use or intranasal: Intranasal Administration Administer nasal solution intranasally as sprays or nasal pumps. Prior to initial use of metered sprays, prime nasal inhaler by depressing the pump firmly several times. Administer nasal spray or pump into each nostril while head is erect. Ophthalmic Administration Administer ophthalmic solution topically to the conjunctiva.
Pediatric Patients Nasal Congestion Intranasal For self-medication in children ≥6 years of age: 2 or 3 sprays of a 0.05% nasal solution in each nostril every 10–12 hours (usually in the morning and evening), up to 2 times daily. Conjunctival Congestion Ophthalmic For self-medication in children ≥6 years of age: 1 or 2 drops of a 0.025% ophthalmic solution in the affected eye(s) every 6 hours as needed. Adults Nasal Congestion Intranasal For self-medication: 2 or 3 sprays of a 0.05% nasal solution in each nostril every 10–12 hours (usually in the morning and evening), up to 2 times daily. Conjunctival Congestion Ophthalmic For self-medication: 1 or 2 drops of a 0.025% ophthalmic solution in the affected eye(s) every 6 hours as needed.
Route of Administration: Nasal
Oxymetazoline had a concentration-dependent inhibitory effect on cultured human nasal CBF from 0.25 to 2.00 g/L.
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:25:58 GMT 2025
Edited
by admin
on Wed Apr 02 08:25:58 GMT 2025
Record UNII
8VLN5B44ZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYMETAZOLINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
OPERIL
Preferred Name English
NASACON
Brand Name English
AFRIN
Brand Name English
OXYMETAZOLINE [VANDF]
Common Name English
Oxymetazoline [WHO-DD]
Common Name English
oxymetazoline [INN]
Common Name English
PHENOL, 3-((4,5-DIHYDRO-1H-IMIDAZOL-2-YL)METHYL)-6-(1,1-DIMETHYLETHYL)-2,4-DIMETHYL-
Systematic Name English
OXYMETAZOLINE [HSDB]
Common Name English
6-TERT-BUTYL-3-(2-IMIDAZOLIN-2-YLMETHYL)-2,4-DIMETHYLPHENOL
Systematic Name English
OXYMETAZOLINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QR01AA05
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
WHO-ATC S01GA04
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
WHO-ATC R01AB07
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
NDF-RT N0000192562
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
WHO-VATC QR01AB07
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
NCI_THESAURUS C29709
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
WHO-ATC R01AA05
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
WHO-VATC QS01GA04
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
216-079-1
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
DRUG CENTRAL
2032
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
ChEMBL
CHEMBL762
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
NCI_THESAURUS
C61871
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
HSDB
3143
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
MERCK INDEX
m8335
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY Merck Index
MESH
D010109
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
CHEBI
7862
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
RXCUI
7812
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB00935
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
SMS_ID
100000083285
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID3040691
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
EVMPD
SUB09567MIG
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
IUPHAR
124
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
DAILYMED
8VLN5B44ZY
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
NDF-RT
N0000011304
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY Imidazolines [Chemical/Ingredient]
PUBCHEM
4636
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
LACTMED
Oxymetazoline
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
FDA UNII
8VLN5B44ZY
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
NDF-RT
N0000009908
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY Vasoconstriction [PE]
INN
1400
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
CAS
1491-59-4
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
WIKIPEDIA
OXYMETAZOLINE
Created by admin on Wed Apr 02 08:25:58 GMT 2025 , Edited by admin on Wed Apr 02 08:25:58 GMT 2025
PRIMARY
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