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

Details

Stereochemistry ACHIRAL
Molecular Formula C16H24N2O.ClH
Molecular Weight 296.836
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OXYMETAZOLINE HYDROCHLORIDE

SMILES

Cl.CC1=CC(=C(O)C(C)=C1CC2=NCCN2)C(C)(C)C

InChI

InChIKey=BEEDODBODQVSIM-UHFFFAOYSA-N
InChI=1S/C16H24N2O.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Evidence for a non-adrenoceptor, imidazoline-mediated contractile response to oxymetazoline in the porcine isolated rectal artery.
2001 Apr
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.
2001 Feb
Reduced baroreceptor sensitivity during hypotension in ANP-knockout mice.
2001 Mar
Effects of N-(2-chloroethyl)-N-ethyl-2-bromobenzylamine (DSP4) on alpha2-adrenoceptors which regulate the synthesis and release of noradrenaline in the rat brain.
2001 Mar
Analysis of ligand activation of alpha 2-adrenoceptor subtypes under conditions of equal G alpha protein stoichiometry.
2001 May
Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee.
2001 May
Renal actions of the alpha2-adrenoceptor agonist, xylazine, in the anaesthetised rat.
2001 Oct
Increased nasal mucosal swelling in subjects with asthma.
2002 Jan
Intracellular sodium modulates the state of protein kinase C phosphorylation of rat proximal tubule Na+,K+-ATPase.
2002 Jun
Effects of oxymetazoline on the ventilation of paranasal sinuses in healthy subjects.
2002 Mar-Apr
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
alpha 2B-Adrenoceptor levels govern agonist and inverse agonist responses in PC12 cells.
2003 Aug 15
Effects of acute, repeated and chronic variable stress on in vivo tyrosine hydroxylase activity and on alpha(2)-adrenoceptor sensitivity in the rat brain.
2003 Dec
Stroke associated with sympathomimetics contained in over-the-counter cough and cold drugs.
2003 Jul
[Acute exposure to imidazoline derivatives in children].
2003 Nov-Dec
Synthesis and identification of two potential oxidation degradants of oxymetazoline.
2004
Chronic rhinosinusitis: management for optimal outcomes.
2004
Antimuscarinic action of oxymetazoline on human intraocular muscles.
2004 Aug
Behavioral effects of serotonin and serotonin agonists in two crayfish species, Procambarus clarkii and Orconectes rusticus.
2004 Dec
The Janus faces of adrenoceptors: factors controlling the coupling of adrenoceptors to multiple signal transduction pathways.
2004 Nov
Differential distribution of functional alph}1-adrenergic receptor subtypes along the rat tail artery.
2005 Aug
Is oxymetazoline really safe for middle ear use.
2005 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 Fri Dec 16 15:57:54 UTC 2022
Edited
by admin
on Fri Dec 16 15:57:54 UTC 2022
Record UNII
K89MJ0S5VY
Record Status Validated (UNII)
Record Version
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Name Type Language
OXYMETAZOLINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
OXYMETAZOLINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [MART.]
Common Name English
KOVANAZE COMPONENT OXYMETAZOLINE HYDROCHLORIDE
Brand Name English
NSC-757254
Code English
UPNEEQ
Brand Name English
AGN-199201
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [JAN]
Common Name English
VISINE L.R.
Brand Name English
SCH-9384
Code English
Oxymetazoline hydrochloride [WHO-DD]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [USAN]
Common Name English
PHENOL, 3-((4,5-DIHYDRO-1H-IMIDAZOL-2-YL)METHYL)-6-(1,1-DIMETHYLETHYL)-2,4-DIMETHYL-, MONOHYDROCHLORIDE
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [VANDF]
Common Name English
OXYMETAZOLINE HYDROCHLORIDE [MI]
Common Name English
6-tert-Butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenol monohydrochloride
Systematic Name English
OCUCLEAR
Brand Name English
OXYMETAZOLINE HCL
Common Name English
OXYMETAZOLINE HYDROCHLORIDE COMPONENT OF KOVANAZE
Brand Name English
SCH 9384
Code English
OXYMETAZOLINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
RHOFADE
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C29709
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
CFR 21 CFR 341.20
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
EU-Orphan Drug EU/3/17/1892
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
Code System Code Type Description
PUBCHEM
66259
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY
MERCK INDEX
M8335
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY Merck Index
CHEBI
7863
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PRIMARY
EPA CompTox
DTXSID80177729
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PRIMARY
ChEMBL
CHEMBL762
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PRIMARY
DAILYMED
K89MJ0S5VY
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY
NSC
757254
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PRIMARY
DRUG BANK
DBSALT000821
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PRIMARY
FDA UNII
K89MJ0S5VY
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PRIMARY
CAS
2315-02-8
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PRIMARY
RXCUI
106101
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY RxNorm
ECHA (EC/EINECS)
219-015-0
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY
NCI_THESAURUS
C29313
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY
RS_ITEM_NUM
1486004
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY
EVMPD
SUB03589MIG
Created by admin on Fri Dec 16 15:57:54 UTC 2022 , Edited by admin on Fri Dec 16 15:57:54 UTC 2022
PRIMARY
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