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
SMILES
CC1=CC(=C(O)C(C)=C1CC2=NCCN2)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)
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 |
DescriptionSources: https://www.drugbank.ca/drugs/DB00935Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/monograph/oxymetazoline-hydrochloride.html
Sources: https://www.drugbank.ca/drugs/DB00935
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/620441 | https://www.ncbi.nlm.nih.gov/pubmed/7437906
Curator's Comment: Oxymetazoline does not cross the blood brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095203 |
4.96 null [pEC50] | ||
0.29 nM [Ki] | |||
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1678720 |
7.73 null [pEC50] | ||
Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1678720 |
7.35 null [pEC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Oxymetazoline Hydrochloride Approved UseTemporary relief of nasal congestion (due to a cold, hay fever, or other upper respiratory allergies) and sinus congestion/pressure. Launch Date6.0721922E11 |
|||
Primary | OCUCLEAR Approved UseRelief of redness of eye due to minor eye irritations Launch Date5.17795185E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 DRUG LABEL https://www.fda.gov/media/98992/download |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 DRUG LABEL https://www.fda.gov/media/98992/download |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.23 h DRUG LABEL https://www.fda.gov/media/98992/download |
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
Dose | Population | Adverse 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... |
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%) Sources: 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%) |
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
AE | Significance | Dose | Population |
---|---|---|---|
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no | |||
Page: 6.0 |
no |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/ Page: 7.0 |
no | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/; Page: 7.0 |
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 Sources: https://pubmed.ncbi.nlm.nih.gov/21177487/; Page: 7.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208552Orig1s000PharmR.pdf#page=19 Page: 19.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Differential capacities of the RGS1, RGS16 and RGS-GAIP regulators of G protein signaling to enhance alpha2A-adrenoreceptor agonist-stimulated GTPase activity of G(o1)alpha. | 2001 Aug |
|
The effect of inferior turbinate hypertrophy on nasal spray distribution to the middle meatus. | 2001 Dec |
|
Clonidine-induced nitric oxide-dependent vasorelaxation mediated by endothelial alpha(2)-adrenoceptor activation. | 2001 Nov |
|
Vasocontractile effects of alpha 2-adrenergic agonists associated with intracellular calcium release. | 2002 |
|
The effects of topical agents of fluticasone propionate, oxymetazoline, and 3% and 0.9% sodium chloride solutions on mucociliary clearance in the therapy of acute bacterial rhinosinusitis in vivo. | 2002 Feb |
|
Mechanism of vascular relaxation by cholinomimetic drugs with special reference to pilocarpine and arecoline. | 2002 Feb |
|
Increased nasal mucosal swelling in subjects with asthma. | 2002 Jan |
|
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 |
|
Naphazoline-induced neuroendocrine changes: increases in ANP and cGMP levels, but suppression of NE, 3H-NE, and cAMP levels in rabbit eyes. | 2002 Jul |
|
[The relationship between ostial patency and medical treatment in acute maxillary sinusitis: an experimental study]. | 2002 Jul-Aug |
|
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 |
|
Desensitization of alpha(2)-adrenoceptors which regulate noradrenaline synthesis and release after chronic treatment with clorgyline in the rat brain. | 2002 May |
|
Topical nasal anesthesia for transnasal fiberoptic laryngoscopy: a prospective, double-blind, cross-over study. | 2003 Apr |
|
Alpha(2A)-adrenergic versus imidazoline receptor controversy in rilmenidine's action: alpha(2A)-antagonism in humans versus alpha(2A)-agonism in rabbits. | 2003 Dec |
|
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 |
|
Functional characterisation of alpha(1)-adrenoceptors in denervated rat vas deferens. | 2003 Jul |
|
Central serous chorioretinopathy associated with administration of sympathomimetic agents. | 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 |
|
[Acute exposure to imidazoline derivatives in children]. | 2003 Nov-Dec |
|
[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 |
|
[Ethyl-3H]RS-79948-197 alpha2-adrenoceptor autoradiography validation in alpha2-adrenoceptor knockout mice. | 2004 Aug 30 |
|
Safety review of benzalkonium chloride used as a preservative in intranasal solutions: an overview of conflicting data and opinions. | 2004 Jan |
|
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 |
|
Controlling bleeding from superficial wounds by the use of topical alpha adrenoreceptor agonists spray. A randomized, masked, controlled study. | 2004 Nov |
|
Allosteric modulation of semicarbazide-sensitive amine oxidase activities in vitro by imidazoline receptor ligands. | 2004 Oct |
|
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 |
|
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 |
|
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 |
|
Is oxymetazoline really safe for middle ear use. | 2005 Jul |
|
Otic barotrauma from air travel. | 2005 May |
|
[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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18666692
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
Edited
Thu Jul 06 22:15:32 UTC 2023
by
admin
on
Thu Jul 06 22:15:32 UTC 2023
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Record UNII |
8VLN5B44ZY
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QR01AA05
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WHO-ATC |
S01GA04
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WHO-ATC |
R01AB07
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NDF-RT |
N0000192562
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WHO-VATC |
QR01AB07
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NCI_THESAURUS |
C29709
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WHO-ATC |
R01AA05
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WHO-VATC |
QS01GA04
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216-079-1
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2032
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CHEMBL762
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C61871
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3143
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M8335
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D010109
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7862
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7812
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DB00935
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100000083285
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DTXSID3040691
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SUB09567MIG
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124
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8VLN5B44ZY
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N0000011304
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PRIMARY | Imidazolines [Chemical/Ingredient] | ||
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4636
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Oxymetazoline
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8VLN5B44ZY
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N0000009908
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PRIMARY | Vasoconstriction [PE] | ||
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1400
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1491-59-4
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OXYMETAZOLINE
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> NON-SUBSTRATE |
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TARGET -> AGONIST |
Binding Assay
IC50
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TARGET -> AGONIST | |||
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METABOLIC ENZYME -> NON-SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> NON-SUBSTRATE |
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METABOLIC ENZYME -> NON-SUBSTRATE |
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TARGET -> AGONIST |
SHORT-ACTING
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METABOLIC ENZYME -> NON-SUBSTRATE |
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
|
||
|
METABOLIC ENZYME -> NON-SUBSTRATE |
|
||
|
TARGET -> AGONIST |
Binding Assay
IC50
|
||
|
METABOLIC ENZYME -> NON-SUBSTRATE |
|
||
|
TARGET -> AGONIST |
IC50
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
IN VITRO
|
||
|
METABOLITE -> PARENT |
IN VITRO
|
||
|
METABOLITE -> PARENT |
IN VITRO
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|