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O0391 Sigma

Olopatadine hydrochloride

≥98% (HPLC)

Synonym: (11Z)-11-[3-(Dimethylamino)propylidene]-6,11-dihydrodibenz[b,e]oxepin-2-acetic acid hydrochloride, AL-4943A, KW-4679, Opatanol, Patanol

  • CAS Number 140462-76-6

  • Empirical Formula (Hill Notation) C21H23NO3·HCl

  • Molecular Weight 373.87

  •  MDL number MFCD00875716

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, O
assay   ≥98% (HPLC)
form   solid
solubility   H2O: ≥20 mg/mL
storage temp.   room temp

Description

Biochem/physiol Actions

Olopatadine is a histamine H1 receptor antagonist and mast cell stabilizer. The low level of occupancy H1 receptors in the brain explains the low sedation effect of olopatidine. It is believed that olopatidine is a substrate for P-glycoprotein, which limits its brain penetration.1

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Olopatadine hydrochloride

United States Pharmacopeia (USP) Reference Standard

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T,N
Risk Statements (Europe) 
Safety Statements (Europe) 
45-61
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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1. P-glycoprotein limits the brain penetration of olopatadine hydrochloride, H1-receptor antagonist Mimura, N., et al. Drug Metab. Pharmacokinet. 23, 106-114, (2008)

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Histamine Stimulates Interleukin-6 Production through Histamine H1 Receptors in Human Amnion Cells. Morimitsu, A., et al Gynecol. Obstet. Invest. 69, 67-72, (2009)

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Intact cell binding for in vitro prediction of sedative and non-sedative histamine H1-receptor antagonists based on receptor internalization. Hishinuma, S., et al J. Pharmacol. Sci. 107, 66-79, (2008)

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Multiple action agents and the eye: do they really stabilize mast cells? Lambiase, A., et al Curr. Opin. Allergy Clin. Immunol. 9, 454-465, (2009)

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The antagonism of histamine H1 and H4 receptors ameliorates chronic allergic dermatitis via anti-pruritic and anti-inflammatory effects in NC/Nga mice. Ohsawa Y and Hirasawa N Allergy 67(8), 1014-22, (2012)

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Advantages of histamine H4 receptor antagonist usage with H1 receptor antagonist for the treatment of murine allergic contact dermatitis. Matsushita A, Seike M, Okawa H, et al. Exp. Dermatol. 21(9), 714-5, (2012)

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[A 10-week safety and efficacy evaluation of olopatadine, 0.2% instilled twice-daily in patients with allergic conjunctivitis in Japan]. Ohno S and Ando M Nippon Ganka Gakkai Zasshi 116(9), 869-79, (2012)

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[Pharmacological profile and clinical efficacy of olopatadine hydrochloride ophthalmic solution (Patanol 0.1% ophthalmic solution)]. Watanabe M, Kodama H, Hasegawa K, et al. Nippon. Yakurigaku Zasshi. 130(3), 221-31, (2007)

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Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug. Ohmori K, Hayashi K, Kaise T, et al. Jpn. J. Pharmacol. 88(4), 379-97, (2002)

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Effects of single therapeutic doses of promethazine, fexofenadine and olopatadine on psychomotor function and histamine-induced wheal- and flare-responses: a randomized double-blind, placebo-controlled study in healthy volunteers. Kamei H, Isaji A, Noda Y, et al. Arch. Dermatol. Res. 304(4), 263-72, (2012)

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Pre-seasonal treatment with topical olopatadine suppresses the clinical symptoms of seasonal allergic conjunctivitis. Shimura M, Yasuda K, Miyazawa A, et al. Am. J. Ophthalmol. 151(4), 697-702.e2, (2011)

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Impairment of fear memory consolidation and expression by antihistamines. Nonaka A, Masuda F, Nomura H, et al. Brain Res. 1493, 19-26, (2013)

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Comparison of effects of alcaftadine and olopatadine on conjunctival epithelium and eosinophil recruitment in a murine model of allergic conjunctivitis. Ono SJ and Lane K Drug Des. Devel. Ther. 5, 77-84, (2011)

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Olopatadine 0.6% nasal spray protects from vasomotor challenge in patients with severe vasomotor rhinitis. Smith PK and Collins J Am. J. Rhinol. Allergy 25(4), e149-52, (2011)

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Stereoselective syntheses of the antihistaminic drug olopatadine and its E-isomer. Bosch J, Bachs J, Gómez AM, et al. J. Org. Chem. 77(14), 6340-4, (2012)

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Two-week comparison study of olopatadine hydrochloride nasal spray 0.6% versus azelastine hydrochloride nasal spray 0.1% in patients with vasomotor rhinitis. Lieberman P, Meltzer EO, LaForce CF, et al. Allergy Asthma Proc. 32(2), 151-8, (2011)

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Effect of intranasal fluticasone furoate and intraocular olopatadine on nasal and ocular allergen-induced symptoms. Baroody FM, Logothetis H, Vishwanath S, et al. Am. J. Rhinol. Allergy 27(1), 48-53, (2013)

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Loteprednol etabonate suspension 0.2% administered QID compared with olopatadine solution 0.1% administered BID in the treatment of seasonal allergic conjunctivitis: a multicenter, randomized, investigator-masked, parallel group study in Chinese patients. Gong L, Sun X, Qu J, et al. Clin. Ther. 34(6), 1259-1272.e1, (2012)

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Comprehensive report of olopatadine 0.6% nasal spray as treatment for children with seasonal allergic rhinitis. Meltzer EO, Blaiss M, and Fairchild CJ Allergy Asthma Proc. 32(3), 213-20, (2011)

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Double dose of cetirizine hydrochloride is effective for patients with urticaria resistant: a prospective, randomized, non-blinded, comparative clinical study and assessment of quality of life. Okubo Y, Shigoka Y, Yamazaki M, et al. J. Dermatolog. Treat. 24(2), 153-60, (2013)

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A rapid and sensitive liquid chromatography-tandem mass spectrometry method for determination of olopatadine concentration in human plasma. Zhu P, Wen YG, Fan XP, et al. J. Anal. Toxicol. 35(2), 113-8, (2011)

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Pharmacokinetic evaluation of olopatadine for the treatment of allergic rhinitis and conjunctivitis. Nickels AS, Dimov V, and Wolf R Expert Opin. Drug Metab. Toxicol. 7(12), 1593-9, (2011)

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Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug. Ohmori K, Hasegawa K, Tamura T, et al. Arzneimittelforschung 54(12), 809-29, (2004)

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The effect of antihistamines on seizures induced by increasing-current electroshocks: ketotifen, but not olopatadine, promotes the seizures in infant rats. Yamada K, Takizawa F, Tamura T, et al. Biol. Pharm. Bull. 35(5), 693-7, (2012)

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Stability-indicating high-performance column liquid chromatography and high-performance thin-layer chromatography methods for the determination of olopatadine hydrochloride in tablet dosage form. Varghese SJ, Kumar AM, and Ravi TK J. AOAC Int. 94(6), 1815-20, (2011)

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Fixed drug eruption induced by topical olopatadine ophthalmic solution. Bilgili SG, Karadag AS, Karadag R, et al. Hum. Exp. Toxicol. 31(12), 1292-4, (2012)

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A multicenter, double-blind, randomized, noninferiority comparison of 14 days' treatment with oral olopatadine 10 mg or cetirizine 10 mg in Chinese adults with cutaneous pruritus. Wang T, Liu Y, Yin J, et al. Pharmacology 91(1-2), 117-22, (2013)

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Olopatadine hydrochloride inhibits capsaicin-induced flare response in humans. Shindo M, Yoshida Y, and Yamamoto O Pharmacology 87(3-4), 152-4, (2011)

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Histamine H1-receptor antagonistic drug olopatadine suppresses TSLP in atopic dermatitis model mice. Higashi M, Ohsawa I, Oda F, et al. Allergol. Int. 62(1), 137-8, (2013)

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Dermatitis induced by estrogen and progesterone: dual positive results on the intradermal skin test. Park JS, Chung KH, Lee MJ, et al. Dermatitis 22(6), 354-7, (2011)

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Olopatadine suppresses the late phase reaction in parthenium dermatitis. Raj A, Lakshmi C, and Srinivas CR Indian J. Dermatol. Venereol. Leprol. 77(6), 711-3, (2011)

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Thermal angiooedema induced by hot water. Kobayashi A, Uhara H, Ashida A, et al. Acta Derm. Venereol. 91(3), 343-4, (2011)

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Merck 14,6840

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