140462-76-6 Usage
Description
Olopatadine hydrochloride is an ophthalmic antihistamine that acts as a potent and selective antagonist of the H1 histamine receptor, with significantly lower affinities for the H2 and H3 receptors. It is effective in inhibiting the release of histamine from mast cells and is used to treat various allergic conditions without causing cognitive or psychomotor impairment at therapeutic doses.
Uses
Used in Pharmaceutical Industry:
Olopatadine hydrochloride is used as an antiallergic and antihistaminic agent for the treatment of allergic rhinitis, conjunctivitis, and chronic urticaria. It is particularly effective in providing temporary relief from itching caused by allergic conjunctivitis and helps in suppressing motion sickness or for sedation due to its central properties.
Used in Ophthalmology:
Olopatadine hydrochloride is used as a mast cell stabilizer and histamine H1 antagonist in the treatment of ocular allergies and conditions involving type 1 immediate hypersensitivity reactions. Its selective action on the H1 receptor and minimal impact on cognitive functions make it a valuable asset in the symptomatic treatment of various immediate hypersensitivity reactions in the eye.
Originator
Kyowa Hakko (Japan)
Preparation
Olopatadine hydrochloride can be prepared in five steps from the sodium salt of phydroxyphenylacetic acid methyl ester with phthalide.
Pharmacokinetics
Olopatadine hydrochloride was launched in the US for use in allergic conjunctivitis. It has a fast onset of action with a long duration of action (due to slow dissociation kinetics) that combines the ability to prevent human conjunctival mast cell mediator release with selective H1-receptor antangonistic activity (greater H3:H1 selectivity than H2:H1 selectivity). In addition, Olopatadine hydrochloride had no inhibition of 5-lipoxygenase, PAF acetyltransferase and thromboxane synthase while interfering with phospholipase A2. It has a presynaptic inhibition of tachykinin release and inhibits bronchial sensory nerves through activation of small conductance calcium activated potassium channels. It was more potent than ketotifen and terfenadine and was effective at inhibition of PAF, LTC4 induced conjunctivitis and TXB2 production. It does not accumulate in the CNS, has a low affinity for H1-receptors in the brain, and significantly inhibits allergen induce sneezing. Olopatadine hydrochloride was more effective in conjuctival than in corneal or the trabecuiar meshwork cells.
Veterinary Drugs and Treatments
Olopatadine HCl is a selective H1 receptor antagonist and inhibitor
of histamine release from mast cells. It is marketed for topical use
to alleviate symptoms of allergic conjunctivitis in humans and is
thought to be safe for use in children three years of age and older.
Olopatadine, upon topical application in humans, was shown to
have very limited systemic absorption. It was detectable in the milk
of nursing rats, after topical application, and like most medications
should be avoided in pregnant or nursing animals.
Check Digit Verification of cas no
The CAS Registry Mumber 140462-76-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,0,4,6 and 2 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 140462-76:
(8*1)+(7*4)+(6*0)+(5*4)+(4*6)+(3*2)+(2*7)+(1*6)=106
106 % 10 = 6
So 140462-76-6 is a valid CAS Registry Number.
InChI:InChI=1/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+;
140462-76-6Relevant articles and documents
Preparation method of olopatadine hydrochloride
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Paragraph 0039; 0044-0045, (2021/11/10)
The method comprises the following steps: [3 - (dimethylamino) propyl] triphenylphosphonium bromide hydrobromide is added into tetrahydrofuran. The sodium hydride and dimethyl sulfoxide are added 11 - oxo -6, 11 - dihydrodibenzo [b, e] oxazepine -2 - acetic acid and stirred until the reaction system forms a black brown suspension reaction. The reaction solution is quenched by a mixed solution of purified water and tetrahydrofuran, and then the aqueous phase is treated with a mixed solvent of hydrochloric acid and n-butanol. The olopatadine hydrochloride is stirred and added with hydrochloric acid to form a white turbid liquid, and then is filtered through stirring after stirring, and is dried to obtain olopatadine hydrochloride, and the prepared oxalolopatadine hydrochloride is high in yield and short in reaction route.
Preparation technique of olopatadine hydrochloride
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Paragraph 0056; 0057, (2016/10/27)
The invention relates to a preparation technique of olopatadine hydrochloride. The technique comprises the following steps: carrying out reaction on 2-(chloromethyl)benzoic acid and p-hydroxyphenylacetic acid to generate Isoxepac, and carrying out reaction on the Isoxepac and a Wittig-horner agent generated by N,N-dimethylaminochloropropane hydrochloride to generate hydrochloride, thereby obtaining the olopatadine hydrochloride. The method uses the low-cost raw materials for reaction, avoids using toxic agents in the reaction process, has the advantages of short process route, mild reaction conditions, controllable operation, short production cycle, low energy consumption, high yield, high purity and safe technique, and is suitable for industrial production.
A PROCESS FOR THE PREPARATION OF OLOPATADINE AND SYLIL INTERMEDIATES THEREOF
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Paragraph 7; 8, (2015/05/19)
The present invention refers to a new "one-pot" process for the preparation of olopatadine via intermediates of formula (III).
