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
SMILES
CN(C)CC\C=C1/C2=C(COC3=C1C=C(CC(O)=O)C=C3)C=CC=C2
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+
DescriptionCurator'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
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1350797 |
16.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | PATANOL Approved UseINDICATIONS & 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 Date1996 |
|||
| Primary | PATANASE Approved UseINDICATIONS 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 Date2008 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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 |
Other AEs: Conjunctivitis viral, Hyperemia... Other AEs: Conjunctivitis viral (1.1%) Sources: Hyperemia (2.3%) Eyes tearing (1.1%) Eye discomfort (1.1%) 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, 32.4 |
Other AEs: Vision blurred, Dry eye... Other AEs: Vision blurred (4.8%) Sources: 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%) |
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) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F Sources: |
Other AEs: Eye discharge, Stinging... Other AEs: Eye discharge (4 patients) Sources: Stinging (4 patients) Blurred vision (4 patients) Dry nose (2 patients) 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, adult |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F 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) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Identification of old drugs as potential inhibitors of HIV-1 integrase - human LEDGF/p75 interaction via molecular docking. | 2012-12 |
|
| Comprehensive review of olopatadine: the molecule and its clinical entities. | 2010-04-22 |
|
| 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. | 2008-12 |
|
| Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats. | 2008-03 |
|
| Histamine-induced vasodilation and vasoconstriction in the mesenteric resistance artery of the rat. | 2006-01-04 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug. | 2004 |
|
| Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug. | 2002-04 |
|
| [Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride' (olopatadine), an antiallergic drug]. | 2001-07 |
|
| Comparative effects of topical ocular anti-allergy drugs on human conjunctival mast cells. | 1997-12 |
|
| The in vitro and in vivo ocular pharmacology of olopatadine (AL-4943A), an effective anti-allergic/antihistaminic agent. | 1996 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16864903
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).
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SALT/SOLVATE (PARENT)
SUBSTANCE RECORD