Olopatadine hydrochloride

Base Information

• Chemical Name: Olopatadine hydrochloride
• CAS No.: 140462-76-6
• Molecular Formula: C21H23NO3·HCl
• Molecular Weight: 373.879
• Hs Code.: 29329990
• European Community (EC) Number: 604-185-4
• UNII: 2XG66W44KF
• DSSTox Substance ID: DTXSID0046486
• Wikidata: Q27255766
• NCI Thesaurus Code: C61867
• RXCUI: 236599
• ChEMBL ID: CHEMBL1719
• Mol file: 140462-76-6.mol

Synonyms:11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin-2-acetic acid;4679, KW;Hydrochloride, Olopatadine;KW 4679;KW 4943A;KW-4679;KW-4943A;KW4943A;olopatadine;olopatadine hydrochloride;Patanol

Chemical Property of Olopatadine hydrochloride

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 9.65E-13mmHg at 25°C
• Melting Point: 242-245 °C
• Boiling Point: 523 °C at 760 mmHg
• Flash Point: 270.1 °C
• PSA: 49.77000
• Density: ==
• LogP: 4.39150
• Storage Temp.: Refrigerator
• Solubility.: H2O: ≥20mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 373.1444713
• Heavy Atom Count: 26
• Complexity: 488

Purity/Quality:

99%, ^*data from raw suppliers

Olopatadine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 45-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC=C1C2=CC=CC=C2COC3=C1C=C(C=C3)CC(=O)O.Cl
• Isomeric SMILES: CN(C)CC/C=C\1/C2=CC=CC=C2COC3=C1C=C(C=C3)CC(=O)O.Cl
• Recent ClinicalTrials: Clinical Efficacy of PRO-118 Compared With Olopatadine Hydrochloride Ophthalmic Solution in Allergic Conjunctivitis
• Recent NIPH Clinical Trials: Evaluation of the efficacy and safety of anti-allergic ophthalmic solution for the treatment of allergic conjunctivitis.
• Description: Olopatadine hydrochloride is an ophthalmic antihistamine that inhibits release of histamine from mast cells and is a relatively selective histamine H1 antagonist. It inhibits type 1 immediate hypersensitivity reactions. Olopatadine hydrochloride is indicated in the temporary relief of itching caused by allergic conjunctivitis. H1 antagonists have an established and valued place in the symptomatic treatment of various immediate hypersensitivity reactions. In addition, the central properties of some of the series are of therapeutic value for suppressing motion sickness or for sedation.
• Uses: Olopatadine hydrochloride is a potent, selective antagonist of the H1 histamine receptor (Ki = 16-41.1 nM), with much lower affinities for the H2 and H3 receptors (Ki = 43.4 and 172 μM, respectively). It blocks histamine-induced phosphoinositide turnover in isolated cells (IC50 = 9.5-39.9 nM) and prevents passive cutaneous anaphylaxis in rats (ED50 = 49 μg/kg) and anaphylactic bronchoconstriction in guinea pigs (ID50 = 30 μg/kg). Olopatadine is effective in treating allergic rhinitis and conjunctivitis. It also suppresses itch in patients with well-controlled chronic urticaria. In humans, this antihistamine does not cause cognitive or psychomotor impairment at therapeutic doses.[Cayman Chemical] Dual acting histamine H1-receptor antagonist and mast cell stabilizer. Antiallergic; antihistaminic.

Technology Process of Olopatadine hydrochloride

There total 52 articles about Olopatadine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid benzyl ester (60548-16-5) + anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide (27710-82-3) → (E )-11-[ 3-(dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid hydrochloride (949141-22-4) + olopatadine hydrochloride (140462-76-6)

Guidance literature:

anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide; With sodium hydride; In tetrahydrofuran; for 3h; Heating / reflux;

(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid benzyl ester; In tetrahydrofuran; at 0 - 30 ℃; for 3h;

With hydrogenchloride; water; In di-isopropyl ether; pH=2;

Reference yield: 95.6%

olopatadine (113806-05-6) → olopatadine hydrochloride (140462-76-6)

Guidance literature:

With hydrogenchloride; In water; acetone; at 5 - 25 ℃; for 2 - 15h; Product distribution / selectivity;

Reference yield: 90.5%

isoxepac (55453-87-7) + N-(3-chloropropyl)-N,N-dimethylamine hydrochloride → olopatadine hydrochloride (140462-76-6)

Guidance literature:

N-(3-chloropropyl)-N,N-dimethylamine hydrochloride; With potassium bromide; for 1h; Inert atmosphere;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In dimethyl sulfoxide; for 2h; Reflux;

isoxepac; In dimethyl sulfoxide; at 20 ℃; for 1h; Reagent/catalyst; Solvent;

upstream raw materials:

olopatadine

(11-oxo-6,11-dihydro-dibenzo[b,e]oxepin-2-yl)-acetic acid benzyl ester

anhydrous 3-(dimethylamino)propyltriphenylphosphonium bromide hydrobromide

(Z)-11-(3-dimethylaminopropylidene)-6,11-dihydrodibenz[b,e] oxepin-2-acetic acid ethyl ester

Refernces

• 1、 -. "A preparation method of olopatadine hydrochloride (by machine translation)". Paragraph 0012; 0023. . Retrieved 2019/10/29.
• 2、 -. "Preparation technique of olopatadine hydrochloride". Paragraph 0056; 0057. . Retrieved 2016/10/27.