Grundinformationen
- Standard-SMILES
CN(C)CC/C=C1/c2ccccc2COc2ccc(CC(=O)O)cc21- InChIKey
JBIMVDZLSHOPLA-LSCVHKIXSA-N- Summenformel
- C21H23NO3
- Durchschnittliche Molmasse
- 337,4 g/mol
- Monoisotopische Masse
- 337,1677936
Überblick
2-[11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid is a heterotricyclic compound.
Namen und Bezeichner
- Bevorzugter Name
- Olopatadine
- IUPAC
- 2-[(11Z)-11-[3-(dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- 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
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,5
- Polarare Oberfläche (TPSA)
- 49,8 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 25
- Formalladung
- 0
- Komplexität
- 488
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Anti-Allergic Agents; Antihistamines;
EMA approved medicines: Human medicine
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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.
Gefahrenhinweise
Toxikologische Informationen
Toxicity Summary
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
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]
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Olopatadine
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
◈ What is olopatadine?
Chemie und Industrie
Pharmakologische Informationen
ATC Code
S01GX09
S - Sensory organs
R - Respiratory system
QS - Sensory organs
QR - Respiratory system
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. 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
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.
Metabolism/Metabolites
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
FDA Pharmacological Classification
D27V6190PM
OLOPATADINE
Physiologic Effects [PE] - Decreased Histamine Release
Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists
Established Pharmacologic Class [EPC] - Histamine-1 Receptor Inhibitor
Established Pharmacologic Class [EPC] - Mast Cell Stabilizer
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment.
Absorption, Distribution and Excretion
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. 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.
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.
In an open-label study consisting of healthy Chinese subjects receiving oral administration of olopatadine, the mean apparent volume of distribution was 133.83 L.
In an open-label study consisting of healthy Chinese subjects receiving oral administration of olopatadine, the mean apparent oral clearance (CL/F) was 23.45 L/h.
Verwendung und Herstellung
Uses
Use (kg) in USA (2002): 18
For the treatment of ocular itching associated with allergic conjunctivitis. Used as an antihistamine. [Wikipedia]
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