Olopatadine | CAS#113806-05-6 | Antihistamine

MedKoo Cat#: 318385 | Name: Olopatadine

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Description:

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

Olopatadine is an antihistamine, as well as anticholinergic and mast cell stabilizer. It is used to treat itching associated with allergic conjunctivitis (eye allergies). There is also a potential for Olopatadine as a treatment modality for steroid rebound (red skin syndrome).

Chemical Structure

Olopatadine

CAS#113806-05-6

Theoretical Analysis

MedKoo Cat#: 318385

Name: Olopatadine

CAS#: 113806-05-6

Chemical Formula: C21H23NO3

Exact Mass: 337.1678

Molecular Weight: 337.41

Elemental Analysis: C, 74.75; H, 6.87; N, 4.15; O, 14.23

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Synonym

Olopatadine, Patanol, KW-4679, KW-4943A, Opatanol

IUPAC/Chemical Name

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

InChi Key

JBIMVDZLSHOPLA-LSCVHKIXSA-N

InChi Code

InChI=1S/C21H23NO3/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)/b18-8-

SMILES Code

O=C(O)CC1=CC=C(OCC2=CC=CC=C2/C3=C/CCN(C)C)C3=C1

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, not in water

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 is an orally active and selective histamine 1 (H1) receptor antagonist and a mast cell stabilizer.

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/

Preparing Stock Solutions

The following data is based on the product molecular weight 337.41 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. 2. 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. 3. 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. 4. 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: Mostafa IM, Omar MA, Noureldeen DAM, Zeid AM, Halawa MI, Mohamed AA. Green and sensitive detection of olopatadine in aqueous humor using a signal-on fluorimetric approach: GREEnness assessment. Luminescence. 2024 Jul;39(7):e4814. doi: 10.1002/bio.4814. PMID: 39011865. 2: Xu JP, Zhang XB, Jiang QX, Wang XY, Liu H, Zhang ZJ, Zeng QW, Cheng L. Efficacy, safety, and serum cytokine modulation by olopatadine hydrochloride and desloratadine citrate disodium combination therapy in urticaria. Am J Transl Res. 2024 Jun 15;16(6):2501-2508. doi: 10.62347/XMFX3074. PMID: 39006257; PMCID: PMC11236624. 3: Nakagawa N, Kashiwabara M, Egawa K, Sasaki A. Cost-effectiveness Analysis of Second-Generation Antihistamine 1 Receptor Blockers and Japanese Kampo Shoseiryuto for Treating Perennial Allergic Rhinitis in Outpatient Settings in Japan. Hosp Pharm. 2024 Aug;59(4):436-443. doi: 10.1177/00185787241229152. Epub 2024 Feb 18. PMID: 38919765; PMCID: PMC11195846. 4: Samoliński B, Wojas O, Lipiec A, Krzych-Fałta E, Walkiewicz A, Borowicz J, Samoliński K. Intranasal combo: fixed-dose combination of mometasone furoate and olopatadine hydrochloride in therapeutic strategies for rhinosinusitis. Otolaryngol Pol. 2023 Dec 4;77(6):43-50. doi: 10.5604/01.3001.0054.0941. PMID: 38706259. 5: Reis IM, Dixon PJ, Sekar P, Chauhan A. Sustained Delivery of Olopatadine from Vitamin-E Loaded Contact Lenses. J Ocul Pharmacol Ther. 2024 Mar;40(2):126-135. doi: 10.1089/jop.2023.0111. PMID: 38489059; PMCID: PMC11265619. 6: Bernstein JA, Bernstein JS, Makol R, Ward S. Allergic Rhinitis: A Review. JAMA. 2024 Mar 12;331(10):866-877. doi: 10.1001/jama.2024.0530. PMID: 38470381. 7: Derayea SM, Badr El-Din KM, Ahmed AS, Khorshed AA, Oraby M. Determination of antihistaminic drugs alcaftadine and olopatadine hydrochloride via ion-pairing with eosin Y as a spectrofluorimetric and spectrophotometric probe: application to dosage forms. BMC Chem. 2024 Feb 22;18(1):40. doi: 10.1186/s13065-024-01137-y. PMID: 38388420; PMCID: PMC10885458. 8: Reich S, Lopez M, Leff J, Herman J. DEXTENZA versus Topical Steroid or Antihistamine Therapy for Treatment of Allergic Conjunctivitis. Clin Ophthalmol. 2024 Feb 14;18:473-480. doi: 10.2147/OPTH.S440840. PMID: 38375441; PMCID: PMC10875166. 9: Mamo ET, Newbold GM, Moorehead SC. Efficacy of the topical antihistamine olopatadine in dogs with experimentally induced allergic conjunctivitis. Vet Ophthalmol. 2023 Dec 8. doi: 10.1111/vop.13168. Epub ahead of print. PMID: 38066706. 10: Marini MC, Berra ML, Girado F, Albera PA, Del Papa MS, Passerini MS, Aguilar AJ. Efficacy and Toxicity Evaluation of Bepotastine Besilate 1.5% Preservative- Free Eye Drops Vs Olopatadine Hydrochloride 0.2% Bak-Preserved Eye Drops in Patients with Allergic Conjunctivitis. Clin Ophthalmol. 2023 Nov 16;17:3477-3489. doi: 10.2147/OPTH.S431889. PMID: 38026598; PMCID: PMC10658941. 11: Jiao X, Qi Y, Gao N, Zhang C, Zhao S, Yang R. Exploration of efficacy and mechanism of 0.05% cyclosporine eye drops (II) monotherapy in allergic conjunctivitis-associated dry eye. Eye (Lond). 2024 Apr;38(5):937-944. doi: 10.1038/s41433-023-02807-2. Epub 2023 Oct 30. PMID: 37904000; PMCID: PMC10965942. 12: 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. 13: Kaur J, Rana P, Matta T, Sodhi RK, Pathania K, Pawar SV, Kuhad A, Kondepudi KK, Kaur T, Dhingra N, Sah SP. Protective effect of olopatadine hydrochloride against LPS-induced acute lung injury: via targeting NF-κB signaling pathway. Inflammopharmacology. 2024 Feb;32(1):603-627. doi: 10.1007/s10787-023-01353-3. Epub 2023 Oct 17. PMID: 37847473. 14: Eltagoury M, Abou Samra W, Ghoneim E. Safety and efficacy of topical tacrolimus 0.03% in the management of vernal keratoconjunctivitis: a non- randomized controlled clinical trial. Med Hypothesis Discov Innov Ophthalmol. 2022 Sep 23;11(2):52-63. doi: 10.51329/mehdiophthal1446. PMID: 37641784; PMCID: PMC10445306. 15: 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. 16: Li S, Zhong S. Comparison of olopatadine with ketotifen for allergic conjunctivitis: a meta-analysis study. Postepy Dermatol Alergol. 2023 Apr;40(2):326-330. doi: 10.5114/ada.2023.127647. Epub 2023 May 31. PMID: 37312902; PMCID: PMC10258714. 17: Mohan S, Kumar S, Kumar GP, Maheswari A, Bhatia A, Sagar A. Assessment of the efficacy of olopatadine 0.1% in the treatment of vernal keratoconjunctivitis in terms of clinical improvement based on total ocular symptom score and ocular surface disease index. Indian J Ophthalmol. 2023 May;71(5):1822-1827. doi: 10.4103/ijo.IJO_2048_22. PMID: 37203036; PMCID: PMC10391378. 18: Cyclosporine ophthalmic emulsion (Verkazia) for vernal keratoconjunctivitis. Med Lett Drugs Ther. 2023 May 1;65(1675):70-72. doi: 10.58347/tml.2023.1675d. PMID: 37155251. 19: Vasudev M, Torabi SJ, Michelle L, Meller LLT, Birkenbeuel JL, Roman KM, Nguyen TV, Kuan EC. The rising cost of rhinologic medications. Ann Allergy Asthma Immunol. 2023 Sep;131(3):327-332. doi: 10.1016/j.anai.2023.04.013. Epub 2023 Apr 23. PMID: 37098404. 20: Ridolo E, Barone A, Nicoletta F, Paoletti G, Heffler E, Malvezzi L, Canonica GW. Intranasal corticosteroid and antihistamine combinations in the treatment of allergic rhinitis: the role of the novel formulation olopatadine/mometasone furoate. Expert Rev Clin Immunol. 2023 Jun;19(6):575-584. doi: 10.1080/1744666X.2023.2200165. Epub 2023 Apr 19. PMID: 37038974.