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 Date1989 |
|||
Primary | OCUCLEAR Approved UseRelief of redness of eye due to minor eye irritations Launch Date1986 |
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 |
---|---|---|
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 |
|
Potent alpha(2A)-adrenoceptor-mediated vasoconstriction by brimonidine in porcine ciliary arteries. | 2001 Aug |
|
The effect of inferior turbinate hypertrophy on nasal spray distribution to the middle meatus. | 2001 Dec |
|
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 |
|
Reduced baroreceptor sensitivity during hypotension in ANP-knockout mice. | 2001 Mar |
|
Inhibition of synovial plasma extravasation by preemptive administration of an antiinflammatory irrigation solution in the rat knee. | 2001 May |
|
[Excitatory effect of noradrenaline on rat airway parasympathetic ganglion neurons]. | 2001 Nov |
|
Renal actions of the alpha2-adrenoceptor agonist, xylazine, in the anaesthetised rat. | 2001 Oct |
|
Endothelial G protein beta-subunits trigger nitric oxide-but not endothelium-derived hyperpolarizing factor-dependent dilation in rabbit resistance arteries. | 2001 Oct 12 |
|
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 stability of oxymetazoline hydrochloride in aqueous solution. | 2002 Jan-Feb |
|
[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 |
|
Pertussis toxin converts hyperpolarizations caused by alpha(2)-adrenoceptor agonists containing an imidazoline moiety into depolarizations in MIN 6 cells. | 2002 Sep |
|
Topical nasal anesthesia for transnasal fiberoptic laryngoscopy: a prospective, double-blind, cross-over study. | 2003 Apr |
|
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 |
|
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 |
|
5-HT7 receptor-mediated relaxation of the oviduct in nonpregnant proestrus pigs. | 2003 Feb 14 |
|
Topical nasal anesthesia and laryngopharyngeal sensory testing: a prospective, double-blind crossover study. | 2003 Jan |
|
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 |
|
Oxymetazoline nasal spray three times daily for four weeks in normal subjects is not associated with rebound congestion or tachyphylaxis. | 2003 Sep |
|
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 |
|
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 |
|
Safety review of benzalkonium chloride used as a preservative in intranasal solutions: an overview of conflicting data and opinions. | 2004 Jan |
|
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 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 |
|
Pharmacological characterization of postjunctional alpha-adrenoceptors in human nasal mucosa. | 2005 Sep-Oct |
|
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
Sat Dec 16 16:48:33 GMT 2023
by
admin
on
Sat Dec 16 16:48:33 GMT 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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Code System | Code | Type | Description | ||
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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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PRIMARY | Merck Index | ||
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D010109
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7862
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7812
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PRIMARY | RxNorm | ||
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DB00935
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100000083285
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DTXSID3040691
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SUB09567MIG
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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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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 |
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METABOLIC ENZYME -> SUBSTRATE |
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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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TARGET -> AGONIST |
IC50
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Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE -> PARENT |
IN VITRO
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METABOLITE REACTIVE TYPE->PARENT |
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METABOLITE -> PARENT |
IN VITRO
|
Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |
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