Olopatadine HCl | CAS#140462-76-6 | histamine H1 antagonist

MedKoo Cat#: 562842 | Name: Olopatadine HCl

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Olopatadine HCl is a relatively selective histamine H1 antagonist. Olopatadine HCl acts by inhibiting histamine induced effects on human conjunctival epithelial cells.

Chemical Structure

Olopatadine HCl

CAS#140462-76-6

Theoretical Analysis

MedKoo Cat#: 562842

Name: Olopatadine HCl

CAS#: 140462-76-6

Chemical Formula: C21H24ClNO3

Exact Mass: 373.1445

Molecular Weight: 373.88

Elemental Analysis: C, 67.46; H, 6.47; Cl, 9.48; N, 3.75; O, 12.84

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 250.00
50mg	USD 410.00
100mg	USD 620.00

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Synonym

Olopatadine HCl; Olopatadine Hydrochloride; Pataday; Patanase; ALO-4943A; ALO 4943A; ALO4943A;

IUPAC/Chemical Name

2-[(11Z)-11-[3-(Dimethylamino)propylidene]-6H-benzo[c][1]benzoxepin-2-yl]acetic acid hydrochloride

InChi Key

HVRLZEKDTUEKQH-NOILCQHBSA-N

InChi Code

InChI=1S/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-;

SMILES Code

O=C(O)CC1=CC=C(OCC2=CC=CC=C2/C3=C/CCN(C)C)C3=C1.[H]Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Olopatadine hydrochloride (ALO4943A) is a histamine blocker used to treat allergic conjunctivitis.

In vitro activity:

The study examined the effect of H1-receptor antagonist olopatadine on the secretory function of cultured rat conjunctival goblet cells (CGC) assessed by enzyme-linked lectin assay employing UEA-I lectin. Histamine up-regulated secretion of mucin MUC5AC and expression of membrane-bound protein MUC16 in CGC. In addition, it increased both [Ca2+]i and the level of phosphorylated ERK. These effects were diminished by preliminary application of olopatadine that probably acted via the ERK signaling pathway. Thus, olopatadine reduced [Ca2+]i and down-regulated ERK phosphorylation by binding to H1-receptors, thereby inhibiting secretion of mucin from histamine-stimulated CGC. Reference: Bull Exp Biol Med. 2021 Oct;171(6):750-754. https://pubmed.ncbi.nlm.nih.gov/34709518/

In vivo activity:

Corneal alkali injury (CI) induced in the right eyes of an eight-week-old male Wister rats, by application of 3 mm diameter filter-papers, soaked for 10 s in 1 N-NaOH, to the right eyes' corneal centers for 30 s, afterward, the filter paper removed, and the rat right eye rinsed with 20 ml normal saline. Olopatadine, in the present work, effectively and dose-dependently enhanced the corneal healing after alkali application, with significant reduction of the corneal opacity and neovascularization scores, besides, it suppressed the augmented corneal IL-1β, VEGF, caspase-3 levels, and nuclear NF-κB immunohistochemical expression, meanwhile it abrogated the corneal histopathological changes, induced by alkali application. Reference: Life Sci. 2018 Aug 15;207:499-507. https://pubmed.ncbi.nlm.nih.gov/30056863/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	13.37
	DMSO	41.4	110.59
	Ethanol	4.1	11.03
	PBS (pH 7.2)	0.5	1.34
	Water	15.9	42.54

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 373.88 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. He M, Qin W, Wu Y, Wang X, Wang Y, Wang X. H1-Receptor Antagonist Olopatadine Inhibits MUC5AC Secretion by Conjunctival Goblet Cells. Bull Exp Biol Med. 2021 Oct;171(6):750-754. doi: 10.1007/s10517-021-05309-x. Epub 2021 Oct 28. PMID: 34709518. 3. Iguchi N, Takeda Y, Sato N, Ukichi K, Katakura A, Ueda K, Narushima T, Higuchi S, Ogasawara K. The antihistamine olopatadine regulates T cell activation in palladium allergy. Int Immunopharmacol. 2016 Jun;35:70-76. doi: 10.1016/j.intimp.2016.03.021. Epub 2016 Mar 29. PMID: 27035718. 4. Kandeel S, Balaha M. Olopatadine enhances recovery of alkali-induced corneal injury in rats. Life Sci. 2018 Aug 15;207:499-507. doi: 10.1016/j.lfs.2018.07.002. Epub 2018 Jul 3. PMID: 30056863. 2. Satake K, Ikeda J, Tamura T, Amano T, Kobayashi K. Olopatadine hydrochloride suppresses hot flashes induced by topical treatment with tacrolimus ointment in rats. Eur J Pharmacol. 2015 Oct 15;765:402-5. doi: 10.1016/j.ejphar.2015.09.008. Epub 2015 Sep 8. PMID: 26362749.

In vitro protocol:

In vivo protocol:

1. Kandeel S, Balaha M. Olopatadine enhances recovery of alkali-induced corneal injury in rats. Life Sci. 2018 Aug 15;207:499-507. doi: 10.1016/j.lfs.2018.07.002. Epub 2018 Jul 3. PMID: 30056863. 2. Satake K, Ikeda J, Tamura T, Amano T, Kobayashi K. Olopatadine hydrochloride suppresses hot flashes induced by topical treatment with tacrolimus ointment in rats. Eur J Pharmacol. 2015 Oct 15;765:402-5. doi: 10.1016/j.ejphar.2015.09.008. Epub 2015 Sep 8. PMID: 26362749.

1: Hammad SF, Rady MM, El-Malla SF. UV spectrophotometric methods for simultaneous determination of ketorolac tromethamine and olopatadine hydrochloride: Application of multiple standard addition for assay of ophthalmic solution. Sci Rep. 2023 Oct 24;13(1):18143. doi: 10.1038/s41598-023-45378-8. PMID: 37875539; PMCID: PMC10598205. 2: Kowtharapu LP, Katari NK, Sandoval CA, Konduru N, Muchakayala SK, Pydimarry SPR, Jonnalagadda SB. Regulatory Perspective Reverse Engineering Analysis of the Mast Cell Stabilizer and the Histamine Receptor Antagonist (Olopatadine HCl): Instrumental and Classical Methods for Multiple Formulations. ACS Omega. 2023 Jun 8;8(24):21485-21492. doi: 10.1021/acsomega.3c00311. PMID: 37360430; PMCID: PMC10285952. 3: Kowtharapu LP, Katari NK, Sandoval CA, Muchakayala SK, Rekulapally VK. Green Liquid Chromatography Method for the Determination of Related Substances Present in Olopatadine HCl Nasal Spray Formulation, Robustness by Design Expert. J AOAC Int. 2022 Sep 6;105(5):1247-1257. doi: 10.1093/jaoacint/qsac072. PMID: 35686891. 4: Kowtharapu LP, Katari NK, Ch S, Sandoval CA, Muchakayala SK, Konduru N. A Quality by Design and green LC technique for the determination of mast cell stabilizer and histamine receptor antagonist (Olopatadine HCl) in multiple formulations. Biomed Chromatogr. 2022 Jun;36(6):e5359. doi: 10.1002/bmc.5359. Epub 2022 Mar 15. PMID: 35203103. 5: Xue Y, Zhang W, Lei Y, Dang M. Novel Polyvinyl Pyrrolidone-Loaded Olopatadine HCl-Laden Doughnut Contact Lens to Treat Allergic Conjunctivitis. J Pharm Sci. 2020 May;109(5):1714-1724. doi: 10.1016/j.xphs.2020.01.022. Epub 2020 Jan 31. PMID: 32007507. 6: Kim SI, Park CY, Fordjuor G, Lee JH, Lee JS, Lee JE. Comparison of cytotoxicities and anti-allergic effects of topical ocular dual-action anti- allergic agents. BMC Ophthalmol. 2019 Nov 8;19(1):217. doi: 10.1186/s12886-019-1228-5. PMID: 31703568; PMCID: PMC6839072. 7: Hampel FC, Pedinoff AJ, Jacobs RL, Caracta CF, Tantry SK. Olopatadine- mometasone combination nasal spray: Evaluation of efficacy and safety in patients with seasonal allergic rhinitis. Allergy Asthma Proc. 2019 Jul 3;40(4):261-272. doi: 10.2500/aap.2019.40.4223. Epub 2019 May 3. PMID: 31053180. 8: da Costa LM, Oliveira de Almeida Leite H, Kassab NM, Singh AK. Green Analytical Methods for the Separation of Seven Antihistamines: Application in Separation of Azelastine and Related Impurities in Nasal Solution. Int J Anal Chem. 2019 Feb 11;2019:9489723. doi: 10.1155/2019/9489723. PMID: 30886632; PMCID: PMC6388312. 9: Ranch KM, Maulvi FA, Naik MJ, Koli AR, Parikh RK, Shah DO. Optimization of a novel in situ gel for sustained ocular drug delivery using Box-Behnken design: In vitro, ex vivo, in vivo and human studies. Int J Pharm. 2019 Jan 10;554:264-275. doi: 10.1016/j.ijpharm.2018.11.016. Epub 2018 Nov 10. PMID: 30423418. 10: Patel D, Sarala N, Datti NP. Topical Olopatadine Hydrochloride versus Ketotifen Fumarate for Allergic Conjunctivitis. J Ophthalmic Vis Res. 2018 Apr- Jun;13(2):119-123. doi: 10.4103/jovr.jovr_85_17. PMID: 29719638; PMCID: PMC5905303. 11: McLaurin E, Bergmann M, Narvekar A, Adewale A, Gomes P, Torkildsen G. Pooled analysis of two studies evaluating efficacy and safety of olopatadine hydrochloride 0.77% in patients with allergic conjunctivitis. Clin Ophthalmol. 2017 Jun 8;11:1089-1097. doi: 10.2147/OPTH.S131830. PMID: 28652694; PMCID: PMC5472412. 12: Havle A, Jain V, Ahmed MF, Shedge S, Dokania V, Bagwe V, Agarwal K. Olopatadine Hydrochloride and Fluticasone Propionate in Topical Treatment of Allergic Rhinitis: A Single Blind Randomised Study. J Clin Diagn Res. 2016 Dec;10(12):MC04-MC07. doi: 10.7860/JCDR/2016/20810.9120. Epub 2016 Dec 1. PMID: 28208892; PMCID: PMC5296465. 13: Łaszcz M, Trzcińska K, Witkowska A, Ciesielska A, Badowska-Rosłonek K, Kuziak K. Structural and Physicochemical Studies of Olopatadine Hydrochloride Conformational Polymorphs. J Pharm Sci. 2016 Aug;105(8):2419-26. doi: 10.1016/j.xphs.2016.05.031. Epub 2016 Jul 1. PMID: 27373838. 14: Fukushima A, Ebihara N. Efficacy of olopatadine versus epinastine for treating allergic conjunctivitis caused by Japanese cedar pollen: a double-blind randomized controlled trial. Adv Ther. 2014 Oct;31(10):1045-58. doi: 10.1007/s12325-014-0156-2. Epub 2014 Oct 1. PMID: 25269854; PMCID: PMC4209092. 15: Mahvan TD, Buckley WA, Hornecker JR. Alcaftadine for the prevention of itching associated with allergic conjunctivitis. Ann Pharmacother. 2012 Jul- Aug;46(7-8):1025-32. doi: 10.1345/aph.1Q755. Epub 2012 Jul 17. PMID: 22811343. 16: Meltzer EO, Garadi R, Laforce C, Chadwick SJ, Berger WE, Gross G, Edwards MR, Crenshaw K, Wall GM. Comparative study of sensory attributes of two antihistamine nasal sprays: olopatadine 0.6% and azelastine 0.1%. Allergy Asthma Proc. 2008 Nov-Dec;29(6):659-68. doi: 10.2500/aap.2008.29.3181. Epub 2008 Dec 6. PMID: 19144261. 17: Hampel FC Jr, Ratner PH, Amar NJ, van Bavel JH, Mohar D, Fairchild CJ, Wall GM, Brubaker MJ, Drake M, Crenshaw KM. Improved quality of life among seasonal allergic rhinitis patients treated with olopatadine HCl nasal spray 0.4% and olopatadine HCl nasal spray 0.6% compared with vehicle placebo. Allergy Asthma Proc. 2006 May-Jun;27(3):202-7. doi: 10.2500/aap.2006.27.2862. PMID: 16913262. 18: Avunduk AM, Tekelioglu Y, Turk A, Akyol N. Comparison of the effects of ketotifen fumarate 0.025% and olopatadine HCl 0.1% ophthalmic solutions in seasonal allergic conjunctivities: a 30-day, randomized, double-masked, artificial tear substitute-controlled trial. Clin Ther. 2005 Sep;27(9):1392-402. doi: 10.1016/j.clinthera.2005.09.013. PMID: 16291412.