General
Preferred name
olopatadine
Synonyms
OLOPATADINE HYDROCHLORIDE ()
KW4679 ()
ALO4943A ()
Olopatadine HCl ()
Olopatadine (hydrochloride) ()
ALO4943A,KW4679 ()
ALO-4943A ()
Pataday ()
KW-4679 ()
Patanase ()
Pazeo ()
Pataday once daily relief ()
Allelock ()
Patanol ()
Pataday twice daily relief ()
Olopatadine (as hydrochloride) ()
Opatanol ()
AL-4943A ()
P&D ID
PD009730
CAS
113806-05-6
140462-76-6
Tags
natural product
drug
available
Approved by
FDA
First approval
1996
Drug Status
approved
Drug indication
Anti-Allergic
Ocular allergy
Allergic conjunctivitis
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE Olopatadine is mainly eliminated through urinary excretion. Following oral administration, about 70% and 17% of the total dose was recovered in the urine and feces, respectively.[L6784]
HALF-LIFE Following ocular administration, the elimination half-life of olopatadine was 3.4 ± 1.2 hours. In oral pharmacokinetics study, the elimination half-life was reported to be 8 to 12 hours.[L6787]
INDICATION Olopatadine is indicated for the symptomatic treatment of ocular itching associated with allergic conjunctivitis as ophthalmic solution.[L6781]; ; In nasal spray, olopatadine is indicated for the symptomatic relief of seasonal allergic rhinitis in patients 12 years of age and older.[L6784]
TOXICITY Based on the findings of an acute toxicity study in animals, the oral LD50 of olopatadine was >1150 mg/kg in mice and >3870 mg/kg in rats.[L6790] The Lowest published toxic dose via the oral route was 20 mg/kg in rat and 0.1 mg/kg in mouse.[MSDS]; ; There are no known reports on overdosage following oral, ophthalmic, or intranasal administration of olopatadine. Likely symptoms of antihistamine overdose may include drowsiness in adults and, initially, agitation and restlessness, followed by drowsiness in children. In case of suspected overdose, supportive and symptomatic treatment is recommended.[L6784]
METABOLISM Olopatadine undergoes hepatic metabolism in a non-extensive manner.[L6784,L6787] Based on oral pharmacokinetic studies, there are at least 6 circulating metabolites in human plasma.[L6784] Following topical ocular application of olopatadine, olopatadine N-oxide is formed by metabolism catalyzed by flavin-containing monooxygenase (FMO) 1 and 3 [L6784] and was detected in the plasma after 4 hours post-dosing in less than 10% of the total plasma in half of the patients.[L6781] Mono-desmethyl olopatadine, or N-desmethyl olopatadine, is formed by CYP3A4 [L6784] and may be detected in minimal levels.[L6781]
ABSORPTION Ocular administration of olopatadine in healthy subjects resulted in the Cmax of 1.6 ± 0.9 ng/mL, which was reached after about 2.0 hours. The AUC was 9.7 ± 4.4 ngxh/mL.[L6781] ; ; The average absolute bioavaiability of intranasal olopatadine is about 57%. Following intranasal administration in healthy subjects, the Cmax of 6.0 ± 8.99 ng/mL at steady-state was reached between 30 minutes to 1 hour after twice daily intranasal administration. The average AUC was 66.0 ± 26.8 ng·h/mL. In patients with seasonal allergic rhinitis, the Cmax of 23.3 ± 6.2 ng/mL at steady-state was reached between 15 minutes and 2 hours post-dosing and the average AUC was 78.0 ± 13.9 ng·h/mL.[L6784]
DESCRIPTION Olopatadine is an antihistamine.
Marketed formulations may contain olopatadine hydrochloride (PubChem CID 5282402). (GtoPdb)
PHARMACODYNAMICS Inflammatory reactions in response to various stimuli are mediated by endogenous mediators and other pro-inflammatory factors. Histamine receptor activation and mast cell degranulation are primary mechanisms that cause inflammatory reactions such as ocular itching, hyperemia, chemosis, eyelid swelling, and tearing of seasonal allergic conjunctivitis.[A179704] Olopatadine is an anti-allergenic molecule and mast cell stabilizer that inhibits the _in vivo_ type 1 immediate hypersensitivity reaction.[L6790] By blocking the effects of histamine, olopatadine works to reduce the symptoms of allergies and inflammation at various sites of administration, including the eyes and nose. It has shown to exert antihistaminic effects in isolated tissues, animal models, and humans.[L6784] Olopatadine also demonstrated dose-dependent inhibition of immunologically-stimulated release of histamine from rat basophilic leukemia cells and human conjunctival mast cells _in vitro_.[A179704] Olopatadine has a relatively rapid onset of action and prolonged duration, where it was shown to mediate anti-histaminic effects at 5 minutes to 24 hours post-administration.[A179704]; ; While olopatadine is a non-sedating antihistamine agent, there have been reports of somnolence in some patients taking nasal olopatadine during clinical trials.[L6784] Temporary blurred vision or other visual disturbances were observed following ophthalmic administration. Olopatadine has negligible effects on alpha-adrenergic, dopamine, muscarinic type 1 and 2, and serotonin receptors.[L6790] In clinical trials, there was no evidence of any effect of olopatadine on QT prolongation was observed following intranasal administration.[L6784]
MOA Histamine is a biogenic vasoactive amine that binds to its receptors, which are G-protein coupled receptors. Signaling through the histamine H1 receptor is thought to primarily promote the activation of inflammatory reactions, such as allergy, asthma, and autoimmune diseases.[A179731] H1 receptor signaling activates the intracellular transcription factors, such as IP3, PLC, PKC, DAG, and intracellular calcium ions, which all work to activate further downstream cascades. Activated downstream cascades lead to the production of cytokines, the release of mast cell inflammatory mediators, synthesis of prostacyclins, activation of platelet factor, as well as the synthesis of nitric oxide, arachidonic acid, and thromboxane, which all contribute to inflammatory reactions.[A179731] ; ; Olopatadine is an anti-allergic molecule that works via several mechanisms. As a mast cell stabilizer, it stabilizes rodent basophils and human conjunctival mast cells and inhibits the immunologically-stimulated release of histamine.[A179704] Olopatadine acts as an antagonist at the histamine H1 receptors with high selectivity, which is explained by a unique receptor binding pocket that consists of the aspartate residue in the third transmembrane helix and other sites in the H1 receptor.[A1170] Upon binding, olopatadine blocks the H1 receptor signaling pathway, inhibiting the release of inflammatory mediators, such as tryptase, prostaglandin D2, TNF-alpha, as well as pro-inflammatory cytokines.[L6790] It also decreases chemotaxis and inhibits eosinophil activation.[L6781] _In vitro_, olopatadine was shown to inhibit epithelial cell intercellular adhesion molecule-1 (ICAM-1), which promotes the recruitment of migrating pro-inflammatory mediators.[A179704]
DESCRIPTION MCH1 antagonist (Tocris Bioactive Compound Library)
DESCRIPTION H1 antagonist; ocular antiallergic agent (Tocriscreen Plus)
DESCRIPTION This active molecular is an antihistamine, anticholinergic and mast cell stabilizer. Olopatadine blocks the action of endogenous histamine. It is used to treat itching associated with allergic conjunctivitis (eye allergies). In Dec 2014, Alcon Research planed a phase III trial for Allergic conjunctivitis in China.In Jan 2015,Registered for Allergic conjunctivitis in USA was completed (Ophthalmic, 0.7%). In Oct 2015, Alcon Research completeD phase III trial in Allergic conjunctivitis in China. (BOC Sciences Bioactive Compounds)
Compound Sets
24
BOC Sciences Bioactive Compounds
olopatadine-cas-113806-05-6-item-81891
Cayman Chemical Bioactives
11999
ChEMBL Approved Drugs
CHEMBL1719
CHEMBL1189432
ChEMBL Drugs
CHEMBL1719
CHEMBL1189432
Drug Repurposing Hub
DrugBank
DB00768
DrugBank Approved Drugs
DB00768
DrugCentral
1986
DrugCentral Approved Drugs
1986
DrugMAP
DMKMWQG
DrugMAP Approved Drugs
DMKMWQG
Guide to Pharmacology
7249
JUMP-Target 1 Compound Set
25271818
MedChem Express Bioactive Compound Library
HY-B0426A
NCATS Inxight Approved Drugs
D27V6190PM
NIH Clinical Collections (NCC)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Olopatadine-hydrochloride(Opatanol)
TargetMol Bioactive Compound Library
T1170
The Spectrum Collection
Tocris Bioactive Compound Library
4241
Tocriscreen Plus
4241
External IDs
61
Properties
(calculated by RDKit )
Molecular Weight
337.17
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
3
Aromatic Ring Count
2
cLogP
3.59
TPSA
49.77
Fraction CSP3
0.29
Chiral centers
0.0
Largest ring
7.0
QED
0.91
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
7-TM Receptors
Pathway
GPCR/G protein
Neuroscience
Immunology/Inflammation
Metabolic Enzyme/Protease
Neuronal Signaling
Target
HT
HRH1, S100A1, S100A12, S100A13, S100A2, S100B
S100B
Endogenous Metabolite
Histamine Receptor
Primary Target
Histamine H1 Receptors
MOA
Antagonist
Histamine Receptor antagonist
Indication
conjunctivitis
Therapeutic Class
Antiallergic Agents
Solubility
Soluble in DMSO
Source data