Olopatadine

HCID 5281071

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Basic information

CAS
113806-05-6
Standard SMILES
CN(C)CC/C=C1/c2ccccc2COc2ccc(CC(=O)O)cc21
InChIKey
JBIMVDZLSHOPLA-LSCVHKIXSA-N
Molecular formula
C21H23NO3
Average molar mass
337.4 g/mol
Monoisotopic mass
337.1677936

Overview

2-[11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid is a heterotricyclic compound.

Names & identifiers

Preferred name
Olopatadine
IUPAC
2-[(11Z)-11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid

Names & synonyms

Olopatadine113806-05-6Opatanol2-[(11Z)-11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acidOlopatadinaAL-4943AD27V6190PM11-((Z)-3-(Dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin-2-acetic acidDTXSID3023390Olopatadinum2-((11Z)-11-(3-(dimethylamino)propylidene)-6H-benzo(c)(1)benzoxepin-2-yl)acetic acid2-((2Z)-2-(3-(dimethylamino)propylidene)-9-oxatricyclo(9.4.0.0^(3,8))pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl)acetic acid
Show more names
2-[(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-5-yl]acetic acidRefChem:56799DTXCID603390R01AC08S01GX092-((2Z)-2-(3-(dimethylamino)propylidene)-9-oxatricyclo(9.4.0.03,8)pentadeca-1(15),3(8),4,6,11,13-hexaen-5-yl)acetic acidPatanolOlopatadine (INN)

Database identifiers

CAS
113806-05-6
PubChem CID
5281071
DTXSID
DTXSID3023390
ChEMBL
CHEMBL1189432
ChEBI
CHEBI:94593
UNII
D27V6190PM
EC Number
601-282-3
Nikkaji
J3.342.980K、J485.528K

Properties

Computed structural propertiesFilling in

XLogP
1.5
Topological polar surface area
49.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
25

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP3.4
Solubility3.13e-02 g/L
Human Drugs · 2 items

Breast Feeding; Lactation; Anti-Allergic Agents; Antihistamines;

EMA approved medicines: Human medicine

Melting Point248 °C
Physical DescriptionSolid

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P316, P318, P321, P330, P391, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Exposure RoutesOphthalmic use of olopatadine usually does not produce measurable plasma concentrations.
Toxicity Summary · 1 item

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.

Signs and Symptoms · 1 item

Its side effects may include headaches (7% of occurrence) burning and stinging (5%), dry eye, foreign body sensation, hyperemia, keratitis, lid edema, pruritus, asthenia, cold syndrome, pharyngitis, rhinitis, sinusitis, and taste perversion. [Wikipedia]

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Olopatadine

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation · 2 items

◉ Summary of Use during Lactation

◈ What is olopatadine?

Chemistry & industry

Pharmacology

ATC Code · 5 items

S01GX09

S - Sensory organs

R - Respiratory system

QS - Sensory organs

QR - Respiratory system

Protein BindingAbout 55% of total olopatadine is bound to human serum proteins, with serum albumin being the primary protein of binding.
Pharmacodynamics · 1 item

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. Olopatadine is an anti-allergenic molecule and mast cell stabilizer that inhibits the _in vivo_ type 1 immediate hypersensitivity reaction. 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. Olopatadine also demonstrated dose-dependent inhibition of immunologically-stimulated release of histamine from rat basophilic leukemia cells and human conjunctival mast cells _in vitro_. 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. While olopatadine is a non-sedating antihistamine agent, there have been reports of somnolence in some patients taking nasal olopatadine during clinical trials. 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. In clinical trials, there was no evidence of any effect of olopatadine on QT prolongation was observed following intranasal administration.

Mechanism of Action · 1 item

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. 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. 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. 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. 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. It also decreases chemotaxis and inhibits eosinophil activation. _In vitro_, olopatadine was shown to inhibit epithelial cell intercellular adhesion molecule-1 (ICAM-1), which promotes the recruitment of migrating pro-inflammatory mediators.

Biological Half-LifeFollowing 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.
Metabolism/Metabolites · 3 items

Olopatadine undergoes hepatic metabolism in a non-extensive manner. Based on oral pharmacokinetic studies, there are at least 6 circulating metabolites in human plasma. Following topical ocular application of olopatadine, olopatadine N-oxide is formed by metabolism catalyzed by flavin-containing monooxygenase (FMO) 1 and 3 and was detected in the plasma after 4 hours post-dosing in less than 10% of the total plasma in half of the patients. Mono-desmethyl olopatadine, or N-desmethyl olopatadine, is formed by CYP3A4 and may be detected in minimal levels.

Olopatadine has known human metabolites that include N-monodemethylolopatadine.

The mono-desmethyl and the N-oxide metabolites have been detected at low concentrations in the urine. Route of Elimination: Elimination was predominantly through renal excretion. Half Life: 3 hours

Uses & manufacturing

Uses · 2 items

Use (kg) in USA (2002): 18

For the treatment of ocular itching associated with allergic conjunctivitis. Used as an antihistamine. [Wikipedia]

Related reactions

2 records

Compound notes

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