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Details

Stereochemistry ACHIRAL
Molecular Formula C21H23NO3
Molecular Weight 337.4122
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLOPATADINE, (E)-

SMILES

CN(C)CC\C=C1/C2=CC=CC=C2COC3=CC=C(CC(O)=O)C=C13

InChI

InChIKey=JBIMVDZLSHOPLA-QGMBQPNBSA-N
InChI=1S/C21H23NO3/c1-22(2)11-5-8-18-17-7-4-3-6-16(17)14-25-20-10-9-15(12-19(18)20)13-21(23)24/h3-4,6-10,12H,5,11,13-14H2,1-2H3,(H,23,24)/b18-8+

HIDE SMILES / InChI

Molecular Formula C21H23NO3
Molecular Weight 337.4122
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB00768 | https://www.drugs.com/cdi/olopatadine-drops.html | http://reference.medscape.com/drug/patanase-olopatadine-intranasal-999491 | http://reference.medscape.com/drug/pataday-patanol-olopatadine-ophthalmic-343635 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021861s011lbl.pdf

Olopatadine is an antihistamine (as well as anticholinergic and mast cell stabilizer) used to treat itching associated with allergic conjunctivitis (eye allergies). Olopatadine is a selective histamine H1 antagonist that binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine. Olopatadine is devoid of effects on alpha-adrenergic, dopamine and muscarinic type 1 and 2 receptors. Some known side effects include a headache (7% of occurrence), eye burning and/or stinging (5%), blurred vision, dry eyes, foreign body sensation, hyperemia, keratitis, eyelid edema, pruritus, asthenia, sore throat (pharyngitis), rhinitis, sinusitis, and taste perversion.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
16.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PATANOL

Approved Use

INDICATIONS & USAGE SECTION PAZEO is indicated for the treatment of ocular itching associated with allergic conjunctivitis. PAZEO is a mast cell stabilizer indicated for the treatment of ocular itching associated with allergic conjunctivitis. (1)

Launch Date

1996
Primary
PATANASE

Approved Use

INDICATIONS AND USAGE. PATANASE Nasal Spray is an H1 receptor antagonist indicated for the relief of the symptoms of seasonal allergic rhinitis in adults and children 6 years of age and older.

Launch Date

2008
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.6 ng/mL
1 drop 1 times / day steady-state, ocular
dose: 1 drop
route of administration: Ocular
experiment type: STEADY-STATE
co-administered:
OLOPATADINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
9.7 ng × h/mL
1 drop 1 times / day steady-state, ocular
dose: 1 drop
route of administration: Ocular
experiment type: STEADY-STATE
co-administered:
OLOPATADINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.4 h
1 drop 1 times / day steady-state, ocular
dose: 1 drop
route of administration: Ocular
experiment type: STEADY-STATE
co-administered:
OLOPATADINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 3-17
n = 88
Health Status: healthy
Condition: asymptomatic eyes
Age Group: 3-17
Sex: M+F
Population Size: 88
Sources:
Other AEs: Conjunctivitis viral, Hyperemia...
Other AEs:
Conjunctivitis viral (1.1%)
Hyperemia (2.3%)
Eyes tearing (1.1%)
Eye discomfort (1.1%)
Corneal staining (1.1%)
Sources:
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Other AEs: Vision blurred, Dry eye...
Other AEs:
Vision blurred (4.8%)
Dry eye (3.3%)
Abnormal sensation in eye (2.1%)
Corneal staining (2.4%)
Conjunctival staining (1.8%)
Eye pruritus (1.5%)
Eye irritation (0.3%)
Headache (1.5%)
Dysgeusia (2.4%)
Upper respiratory tract infection (1.8%)
Nasopharyngitis (1.8%)
Ligament sprain (0.3%)
Cough (0.3%)
Sources:
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33 years (range: 4-77 years)
n = 91
Health Status: unhealthy
Condition: conjunctivitis, seasonal allergic
Age Group: 33 years (range: 4-77 years)
Sex: M+F
Population Size: 91
Sources:
Other AEs: Eye discharge, Stinging...
Other AEs:
Eye discharge (4 patients)
Stinging (4 patients)
Blurred vision (4 patients)
Dry nose (2 patients)
Taste perversion (2 patients)
Sources:
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, adult
n = 25
Health Status: unhealthy
Condition: ocular allergy | dry eye, mild-to-moderate
Age Group: adult
Sex: M+F
Population Size: 25
Sources:
AEs

AEs

AESignificanceDosePopulation
Conjunctivitis viral 1.1%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 3-17
n = 88
Health Status: healthy
Condition: asymptomatic eyes
Age Group: 3-17
Sex: M+F
Population Size: 88
Sources:
Corneal staining 1.1%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 3-17
n = 88
Health Status: healthy
Condition: asymptomatic eyes
Age Group: 3-17
Sex: M+F
Population Size: 88
Sources:
Eye discomfort 1.1%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 3-17
n = 88
Health Status: healthy
Condition: asymptomatic eyes
Age Group: 3-17
Sex: M+F
Population Size: 88
Sources:
Eyes tearing 1.1%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 3-17
n = 88
Health Status: healthy
Condition: asymptomatic eyes
Age Group: 3-17
Sex: M+F
Population Size: 88
Sources:
Hyperemia 2.3%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 3-17
n = 88
Health Status: healthy
Condition: asymptomatic eyes
Age Group: 3-17
Sex: M+F
Population Size: 88
Sources:
Cough 0.3%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Eye irritation 0.3%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Ligament sprain 0.3%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Eye pruritus 1.5%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Headache 1.5%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Conjunctival staining 1.8%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Nasopharyngitis 1.8%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Upper respiratory tract infection 1.8%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Abnormal sensation in eye 2.1%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Corneal staining 2.4%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Dysgeusia 2.4%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Dry eye 3.3%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Vision blurred 4.8%
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
healthy, 32.4
n = 330
Health Status: healthy
Age Group: 32.4
Sex: M+F
Population Size: 330
Sources:
Dry nose 2 patients
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33 years (range: 4-77 years)
n = 91
Health Status: unhealthy
Condition: conjunctivitis, seasonal allergic
Age Group: 33 years (range: 4-77 years)
Sex: M+F
Population Size: 91
Sources:
Taste perversion 2 patients
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33 years (range: 4-77 years)
n = 91
Health Status: unhealthy
Condition: conjunctivitis, seasonal allergic
Age Group: 33 years (range: 4-77 years)
Sex: M+F
Population Size: 91
Sources:
Blurred vision 4 patients
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33 years (range: 4-77 years)
n = 91
Health Status: unhealthy
Condition: conjunctivitis, seasonal allergic
Age Group: 33 years (range: 4-77 years)
Sex: M+F
Population Size: 91
Sources:
Eye discharge 4 patients
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33 years (range: 4-77 years)
n = 91
Health Status: unhealthy
Condition: conjunctivitis, seasonal allergic
Age Group: 33 years (range: 4-77 years)
Sex: M+F
Population Size: 91
Sources:
Stinging 4 patients
1 drop 1 times / day multiple, ophthalmic
Recommended
Dose: 1 drop, 1 times / day
Route: ophthalmic
Route: multiple
Dose: 1 drop, 1 times / day
Sources:
unhealthy, 33 years (range: 4-77 years)
n = 91
Health Status: unhealthy
Condition: conjunctivitis, seasonal allergic
Age Group: 33 years (range: 4-77 years)
Sex: M+F
Population Size: 91
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The in vitro and in vivo ocular pharmacology of olopatadine (AL-4943A), an effective anti-allergic/antihistaminic agent.
1996 Winter
Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug.
2002 Apr
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Comprehensive review of olopatadine: the molecule and its clinical entities.
2010 Mar-Apr
Patents

Sample Use Guides

0.1% solution (Patanol): 1 gtt BID in affected eye(s) at an interval of 6-8 hr 0.2% solution (Pataday): 1 gtt in affected eye(s) qDay 0.7% (Pazeo): 1 gtt in affected eye(s) qDay
Route of Administration: Topical
The migration of THP-1 monocytes was studied using a Chemotaxicell 24-well disposable chamber with 5 μm pores (Kurabo Industries Ltd, Osaka, Japan). Cultured cells were harvested and washed three times with Hank’s balanced salt solution and then resuspended in assay medium (RPMI 1640 with 0.5 vol% heat-inactivated FBS, 10 mmol/L N-(2-hydroxyethyl)piperazine-N’-(4-butanesulfonic acid), pH 7.4). Olopatadine and stimulant were premixed in the assay medium and incubated at 37◦C for 30min. Then 0.05mL of the mixture was placed into the lower chamber contained 0.45 mL/well of the assay medium. Then 0.2mL of cell suspension (6 x 10^5 cells) was added to the upper chamber and incubated for 3 h at 37◦C in 5% CO2. Cells passing through the membrane were collected from the lower well and counted with the EPICS XL/MCL flow cytometry system (Beckman Coulter, Fullerton, Calif, USA) followed by mixing of a predetermined number of flow-count fluorospheres (Beckman Coulter).
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:03:03 GMT 2023
Edited
by admin
on Sat Dec 16 10:03:03 GMT 2023
Record UNII
KU3MJP076O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLOPATADINE, (E)-
Common Name English
OLOPATADINE HYDROCHLORIDE IMPURITY, OLOPATADINE E-ISOMER- [USP IMPURITY]
Common Name English
DIBENZ(B,E)OXEPIN-2-ACETIC ACID, 11-(3-(DIMETHYLAMINO)PROPYLIDENE)-6,11-DIHYDRO-, (11E)-
Systematic Name English
OLOPATADINE E-ISOMER
Common Name English
11-((E)-3-(DIMETHYLAMINO)PROPYLIDENE)-6,11-DIHYDRODIBENZ(B,E)OXEPIN-2-ACETIC ACID
Systematic Name English
Code System Code Type Description
FDA UNII
KU3MJP076O
Created by admin on Sat Dec 16 10:03:04 GMT 2023 , Edited by admin on Sat Dec 16 10:03:04 GMT 2023
PRIMARY
PUBCHEM
5284599
Created by admin on Sat Dec 16 10:03:04 GMT 2023 , Edited by admin on Sat Dec 16 10:03:04 GMT 2023
PRIMARY
CAS
113806-06-7
Created by admin on Sat Dec 16 10:03:04 GMT 2023 , Edited by admin on Sat Dec 16 10:03:04 GMT 2023
PRIMARY
EPA CompTox
DTXSID20150556
Created by admin on Sat Dec 16 10:03:04 GMT 2023 , Edited by admin on Sat Dec 16 10:03:04 GMT 2023
PRIMARY
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