OLOPATADINE HYDROCHLORIDE

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 Search

SMILES

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

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/20688slr016_patanol_lbl.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
Histamine H1 receptor 316 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1350797	Antagonist 2849		16.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic conjunctivitis 101 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/20688slr016_patanol_lbl.pdf	Primary		Approved 8583	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
Seasonal allergic rhinitis 64 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021861s011lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
1.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206276s000lbl.pdf	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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206276s000lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.4 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2015/206276s000lbl.pdf	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: https://pubmed.ncbi.nlm.nih.gov/17803435/	healthy, 3-17 Health Status: healthy Age Group: 3-17 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/17803435/	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: https://pubmed.ncbi.nlm.nih.gov/17803435/
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: https://pubmed.ncbi.nlm.nih.gov/28435218/	healthy, 32.4 Health Status: healthy Age Group: 32.4 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/28435218/	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: https://pubmed.ncbi.nlm.nih.gov/28435218/
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: https://pubmed.ncbi.nlm.nih.gov/12462286/	unhealthy, 33 years (range: 4-77 years) Health Status: unhealthy Age Group: 33 years (range: 4-77 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12462286/	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: https://pubmed.ncbi.nlm.nih.gov/12462286/
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: https://pubmed.ncbi.nlm.nih.gov/18167176/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/18167176/	Sources: https://pubmed.ncbi.nlm.nih.gov/18167176/

AEs

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA0009O6	https://www.aablocks.com/goods/Goods/detail?id=AA0009O6
Aaron Chemicals	AR000AFY	http://www.aaronchem.com/113806-05-6
Achemtek	0104-016465	http://www.achemtek.com/113806-05-6
AHH Chemical co.,ltd	MT-01127	http://www.ahhchemical.com/product/MT-01127.html
Alichem	19095690	http://www.alichem.com/en/products/113806-05-6.html
Ambinter	Amb19795461	http://www.ambinter.com/reference/19795461
Ambinter	Amb20239432	http://www.ambinter.com/reference/20239432
Ambinter	Amb20243193	http://www.ambinter.com/reference/20243193
Ambinter	Amb22729271	http://www.ambinter.com/reference/22729271
Aurora Fine Chemicals LLC	A12.866.664	http://online.aurorafinechemicals.com/info?ID=A12.866.664
AvaChem Scientific	2975B	http://www.avachem.com/productSearch.asp?2975B
BioChemPartner	BCP12203	http://www.biochempartner.com/113806-05-6-BCP12203
BLD Pharm	BD146191	http://www.bldpharm.com/products/113806-05-6.html
Chem Scene	CS-0053963	http://www.chemscene.com/113806-05-6.html
ChemMol	49421387	http://www.chemmol.com/chemmol/49421387.html
Chemspace	CSSB00020675518	https://chem-space.com/CSSB00020675518
DC Chemicals	DC31787	http://www.dcchemicals.com//product_show-Olopatadine.html
eNovation Chemicals	D675149	https://www.enovationchem.com/ProductDetails.asp?ProductID=D675149
iChemical	EBD48084	http://www.ichemical.com/chemicals/cas-113806-05-6
Lab Network	LN01300671	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01300671
Matrix Scientific	124926	https://www.matrixscientific.com/124926.html
OChem	3517	http://www.ocheminc.com/index.php?act=psearch&pid=806O056
Smolecule	S538046	http://www.smolecule.com/products/s538046
Synblock Inc	SB10717	http://www.synblock.com/product/113806-05-6.html
THE BioTek	bt-277358	https://www.thebiotek.com/product/inhibitors/bt-277358
Yuhao Chemical	JZ1725	http://www.chemyuhao.com/113806-05-6.html

PubMed

Title	Date	PubMed
Identification of old drugs as potential inhibitors of HIV-1 integrase - human LEDGF/p75 interaction via molecular docking.	2012-12	22733274
Comprehensive review of olopatadine: the molecule and its clinical entities.	2010-04-22	20406593
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	19075512
Progress in allergy signal research on mast cells: up-regulation of histamine signal-related gene expression in allergy model rats.	2008-03	18360087
Histamine-induced vasodilation and vasoconstriction in the mesenteric resistance artery of the rat.	2006-01-04	16337938
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug.	2004	15646365
Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug.	2002-04	12046981
[Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride' (olopatadine), an antiallergic drug].	2001-07	11496828
Comparative effects of topical ocular anti-allergy drugs on human conjunctival mast cells.	1997-12	9433371
The in vitro and in vivo ocular pharmacology of olopatadine (AL-4943A), an effective anti-allergic/antihistaminic agent.	1996	8951675

Patents

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).

Name

Type

Language

OLOPATADINE HYDROCHLORIDE

Official Name

English

ALLELOCK

Preferred Name

English

OLOPATADINE HYDROCHLORIDE [USP-RS]

Common Name

English

KW-4679

Code

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 [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)