U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N2O
Molecular Weight 260.3752
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYMETAZOLINE

SMILES

Cc1cc(c(c(C)c1CC2=NCCN2)O)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 260.3752
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

6.0721922E11
Primary
OCUCLEAR

Approved Use

Relief of redness of eye due to minor eye irritations

Launch Date

5.17795185E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60.5 pg/mL
20 mg single, topical
dose: 20 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
OXYMETAZOLINE unknown
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 unknown
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
895 pg × h/mL
20 mg single, topical
dose: 20 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
OXYMETAZOLINE unknown
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 unknown
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 unknown
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
n = 1
Health Status: unhealthy
Age Group: 4 years
Sex: M
Population Size: 1
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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
Condition: Erythema
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
n = 1
Health Status: unhealthy
Age Group: 4 years
Sex: M
Population Size: 1
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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)
n = 440
Health Status: unhealthy
Condition: Erythema
Age Group: 53.1 years (range: 19–81 years)
Sex: M+F
Population Size: 440
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
Microphysiometric analysis of human alpha1a-adrenoceptor expressed in Chinese hamster ovary cells.
1999 Jun
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.
1999 May
The effect of inferior turbinate hypertrophy on nasal spray distribution to the middle meatus.
2001 Dec
Receptor reserve analysis of the human alpha(2C)-adrenoceptor using.
2001 Jan 12
Frequency dependent alpha(2)-adrenoceptor mediated modulation of excitatory junction potentials in guinea-pig mesenteric artery.
2001 Jan 5
Involvement of the opioid system in the central antisecretory action of alpha-2 adrenoceptor agonists in rat.
2001 Jan-Dec
Prejunctional actions of methylenedioxymethamphetamine in vas deferens from wild-type and alpha(2A/D)-adrenoceptor knockout mice.
2001 Jul 6
Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists.
2001 Jul 6
Analysis of ligand activation of alpha 2-adrenoceptor subtypes under conditions of equal G alpha protein stoichiometry.
2001 May
Intranasal application of the alpha2-adrenoceptor agonist BHT-920 produces decongestion in the cat.
2001 Nov-Dec
Renal actions of the alpha2-adrenoceptor agonist, xylazine, in the anaesthetised rat.
2001 Oct
A study of the effect of nasal steroid sprays in perennial allergic rhinitis patients with rhinitis medicamentosa.
2001 Sep
Endothelial inhibitory modulation on the contractile responses to alpha 2-adrenergic agonists.
2002
Hypertonic saline nasal provocation and acoustic rhinometry.
2002 Apr
Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline.
2002 Feb
Involvement of central K(ATP) channels in the gastric antisecretory action of alpha2-adrenoceptor agonists and beta-endorphin in rats.
2002 Jan 25
Acute exudative inflammation and nasally exhaled nitric oxide are two independent phenomena.
2002 Jan-Feb
Segmental analysis of nasal cavity compliance by acoustic rhinometry.
2002 Jul
Improved strategies and new treatment options for allergic rhinitis.
2002 Jun
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Pertussis toxin converts hyperpolarizations caused by alpha(2)-adrenoceptor agonists containing an imidazoline moiety into depolarizations in MIN 6 cells.
2002 Sep
Stimulation of interleukin-12 production in mouse macrophages via activation of p38 mitogen-activated protein kinase by alpha2-adrenoceptor agonists.
2003 Apr 25
Evidence for the role of alpha1D- and alpha1A-adrenoceptors in contraction of the rat mesenteric artery.
2003 Feb
5-HT7 receptor-mediated relaxation of the oviduct in nonpregnant proestrus pigs.
2003 Feb 14
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens.
2003 Jul
[Tolerance and effectiveness of oxymetazoline and xylometazoline in treatment of acute rhinitis].
2003 Oct
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
Chromatography studies on bio-affinity of nine ligands of alpha1-adrenoceptor to alpha1D subtypes overexpressed in cell membrane.
2004 Aug
Behavioral effects of serotonin and serotonin agonists in two crayfish species, Procambarus clarkii and Orconectes rusticus.
2004 Dec
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
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
Characterisation of alpha2-adrenoceptor subtypes involved in gastric emptying, gastric motility and gastric mucosal defence.
2005 Dec 28
Oxymetazoline is equivalent to ciprofloxacin in preventing postoperative otorrhea or tympanostomy tube obstruction.
2005 Feb
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
In situ gelling, bioadhesive nasal inserts for extended drug delivery: in vitro characterization of a new nasal dosage form.
2006 Jan
Human breast cell lines exhibit functional alpha2-adrenoceptors.
2006 Jul
Simultaneous determination of triamcinolone acetonide and oxymetazoline hydrochloride in nasal spray formulations by HPLC.
2006 Mar 18
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 Sat Jun 26 00:25:23 UTC 2021
Edited
by admin
on Sat Jun 26 00:25:23 UTC 2021
Record UNII
8VLN5B44ZY
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OXYMETAZOLINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NASACON
Brand Name English
AFRIN
Brand Name English
OXYMETAZOLINE [WHO-DD]
Common Name English
OPERIL
Brand Name English
OXYMETAZOLINE [VANDF]
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 Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
WHO-ATC S01GA04
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
WHO-ATC R01AB07
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
NDF-RT N0000192562
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
WHO-VATC QR01AB07
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
NCI_THESAURUS C29709
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
WHO-ATC R01AA05
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
WHO-VATC QS01GA04
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
216-079-1
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
DRUG CENTRAL
2032
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
ChEMBL
CHEMBL762
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
NCI_THESAURUS
C61871
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
HSDB
3143
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
MERCK INDEX
M8335
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY Merck Index
MESH
D010109
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
RXCUI
7812
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00935
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
EPA CompTox
1491-59-4
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
EVMPD
SUB09567MIG
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
IUPHAR
124
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
NDF-RT
N0000011304
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY Imidazolines [Chemical/Ingredient]
PUBCHEM
4636
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
LACTMED
Oxymetazoline
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
FDA UNII
8VLN5B44ZY
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
NDF-RT
N0000009908
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY Vasoconstriction [PE]
INN
1400
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
CAS
1491-59-4
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
WIKIPEDIA
OXYMETAZOLINE
Created by admin on Sat Jun 26 00:25:24 UTC 2021 , Edited by admin on Sat Jun 26 00:25:24 UTC 2021
PRIMARY
Related Record Type Details
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SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> NON-SUBSTRATE
METABOLIC ENZYME -> NON-SUBSTRATE
METABOLIC ENZYME -> NON-SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> NON-SUBSTRATE
METABOLIC ENZYME -> NON-SUBSTRATE
TARGET -> AGONIST
SHORT-ACTING
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