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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

SMILES

CN(C)CC\C=C1\C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2

InChI

InChIKey=JBIMVDZLSHOPLA-LSCVHKIXSA-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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
16.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PATANOL
Primary
PATANASE

Cmax

ValueDoseCo-administeredAnalytePopulation
1.6 ng/mL
1 drop 1 times / day steady-state, ocular
OLOPATADINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
9.7 ng × h/mL
1 drop 1 times / day steady-state, ocular
OLOPATADINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.4 h
1 drop 1 times / day steady-state, ocular
OLOPATADINE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
D27V6190PM
Record Status Validated (UNII)
Record Version