U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C21H23NO3.ClH
Molecular Weight 373.873
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLOPATADINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=HVRLZEKDTUEKQH-NOILCQHBSA-N
InChI=1S/C21H23NO3.ClH/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);1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug.
2004
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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 Fri Dec 15 15:41:47 UTC 2023
Edited
by admin
on Fri Dec 15 15:41:47 UTC 2023
Record UNII
2XG66W44KF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLOPATADINE HYDROCHLORIDE
EMA EPAR   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
OLOPATADINE HYDROCHLORIDE [USP-RS]
Common Name English
KW-4679
Code English
ALLELOCK
Brand Name English
OLOPATADINE HYDROCHLORIDE [JAN]
Common Name English
ALO-4943A
Code English
OLOPATADINE HYDROCHLORIDE [MI]
Common Name English
OLOPATADINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
OLOPATADINE HYDROCHLORIDE [USAN]
Common Name English
OLOPATADINE HYDROCHLORIDE COMPONENT OF RYALTRIS
Brand Name English
OLOPATADINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PAZEO
Brand Name English
DIBENZ(B,E)OXEPIN-2-ACETIC ACID, 11-(3-(DIMETHYLAMINO)PROPYLIDENE)-6,11-DIHYDRO-, HYDROCHLORIDE, (Z)-
Common Name English
KW4679
Code English
OLOPATADINE HCL
Common Name English
PATANASE
Brand Name English
OLOPATADINE (AS HYDROCHLORIDE)
Common Name English
OLOPATADINE HYDROCHLORIDE [EMA EPAR]
Common Name English
ALO4943A
Code English
PATANOL
Brand Name English
PATADAY
Brand Name English
OLOPATADINE HYDROCHLORIDE [MART.]
Common Name English
Olopatadine hydrochloride [WHO-DD]
Common Name English
RYALTRIS COMPONENT OLOPATADINE HYDROCHLORIDE
Brand Name English
OLOPATADINE HYDROCHLORIDE [VANDF]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS OPATANOL (AUTHORIZED: CONJUNCTIVITIS, ALLERGIC)
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
EMA ASSESSMENT REPORTS OPATANOL (AUTHORIZED: CONJUNCTIVITIS, ALLERGIC )
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
Code System Code Type Description
CAS
140462-76-6
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
RS_ITEM_NUM
1478403
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
SMS_ID
100000092187
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
EVMPD
SUB03509MIG
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
NCI_THESAURUS
C61867
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
PUBCHEM
5282402
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
FDA UNII
2XG66W44KF
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
DAILYMED
2XG66W44KF
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
ChEMBL
CHEMBL1189432
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
EPA CompTox
DTXSID0046486
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
RXCUI
236599
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY RxNorm
DRUG BANK
DBSALT000685
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
USAN
HH-31
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY
MERCK INDEX
m8204
Created by admin on Fri Dec 15 15:41:47 UTC 2023 , Edited by admin on Fri Dec 15 15:41:47 UTC 2023
PRIMARY Merck Index
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