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Details

Stereochemistry ACHIRAL
Molecular Formula C21H23NO3
Molecular Weight 337.413
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLOPATADINE

SMILES

CN(C)CC/C(/[H])=C\1/c2ccccc2COc3ccc(cc13)CC(=O)O

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 337.413
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

8.5086719E11
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

1.20821763E12
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
Comparative effects of topical ocular anti-allergy drugs on human conjunctival mast cells.
1997 Dec
[Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride' (olopatadine), an antiallergic drug].
2001 Jul
Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug.
2002 Apr
Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug.
2004
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Histamine-induced vasodilation and vasoconstriction in the mesenteric resistance artery of the rat.
2006 Jan 4
Repeated pre-treatment with antihistamines suppresses [corrected] transcriptional up-regulations of histamine H(1) receptor and interleukin-4 genes in toluene-2,4-diisocyanate-sensitized rats.
2008 Dec
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.
2008 Mar
Comprehensive review of olopatadine: the molecule and its clinical entities.
2010 Mar-Apr
Identification of old drugs as potential inhibitors of HIV-1 integrase - human LEDGF/p75 interaction via molecular docking.
2012 Dec
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 Jun 26 10:38:02 UTC 2021
Edited
by admin
on Sat Jun 26 10:38:02 UTC 2021
Record UNII
D27V6190PM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLOPATADINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
OLOPATADINE [WHO-DD]
Common Name English
OLOPATADINE [VANDF]
Common Name English
OLOPATADINE [INN]
Common Name English
OPATANOL
Brand Name English
OLOPATADINE [MI]
Common Name English
11-((Z)-3-(DIMETHYLAMINO)PROPYLIDENE)-6,11-DIHYDRODIBENZ(B,E)OXEPIN-2-ACETIC ACID
Systematic Name English
AL-4943A
Code English
DIBENZ(B,E)OXEPIN-2-ACETIC ACID, 11-(3-(DIMETHYLAMINO)PROPYLIDENE)-6,11-DIHYDRO-, (Z)-
Common Name English
Classification Tree Code System Code
WHO-ATC R01AC08
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
NDF-RT N0000175519
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
WHO-VATC QS01GX09
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
NCI_THESAURUS C29578
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
NDF-RT N0000000190
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
WHO-VATC QR01AC08
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
WHO-ATC S01GX09
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
NDF-RT N0000175628
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
Code System Code Type Description
EVMPD
SUB09431MIG
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
PUBCHEM
5281071
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
WIKIPEDIA
OLOPATADINE
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
MERCK INDEX
M8204
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00768
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
IUPHAR
7249
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
EPA CompTox
113806-05-6
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
FDA UNII
D27V6190PM
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
ChEMBL
CHEMBL1189432
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
LACTMED
Olopatadine
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
DRUG CENTRAL
1986
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
INN
7257
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
RXCUI
135391
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY RxNorm
CAS
113806-05-6
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
MESH
C074921
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
NCI_THESAURUS
C61866
Created by admin on Sat Jun 26 10:38:02 UTC 2021 , Edited by admin on Sat Jun 26 10:38:02 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE -> PARENT
MINOR
METABOLITE LESS ACTIVE -> PARENT
primarily catalyzed by FMO1 and FMO3
MINOR
METABOLITE ACTIVE -> PARENT
N-desmethyl olopatadine (Ml) formation was catalyzed mainly by CYP3A4
MAJOR
METABOLITE LESS ACTIVE -> PARENT
MINOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC