Olopatadine
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MedKoo CAT#: 318385

CAS#: 113806-05-6

Description: 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

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Olopatadine
CAS# 113806-05-6
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318385
Name: Olopatadine
CAS#: 113806-05-6
Chemical Formula: C21H23NO3
Exact Mass: 337.17
Molecular Weight: 337.412
Elemental Analysis: C, 74.75; H, 6.87; N, 4.15; O, 14.23

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:
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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.

Recalculate based on batch purity %
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: 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.
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.

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1: Olopatadine for the Treatment of Allergic Conjunctivitis: A Review of the Clinical Efficacy, Safety, and Cost-Effectiveness [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2016 Mar 17. Available from http://www.ncbi.nlm.nih.gov/books/NBK355639/ PubMed PMID: 27077162.

2: Nickels AS, Dimov V, Wolf R. Pharmacokinetic evaluation of olopatadine for the treatment of allergic rhinitis and conjunctivitis. Expert Opin Drug Metab Toxicol. 2011 Dec;7(12):1593-9. doi: 10.1517/17425255.2011.630389. Epub 2011 Oct 28. Review. PubMed PMID: 22032416.

3: Roland PS, Ryan MW, Wall GM. Olopatadine nasal spray for the treatment of seasonal allergic rhinitis in patients aged 6 years and older. Expert Opin Pharmacother. 2010 Jun;11(9):1559-67. doi: 10.1517/14656566.2010.485609. Review. PubMed PMID: 20482305.

4: Leonardi A, Quintieri L. Olopatadine: a drug for allergic conjunctivitis targeting the mast cell. Expert Opin Pharmacother. 2010 Apr;11(6):969-81. doi: 10.1517/14656561003694643. Review. PubMed PMID: 20307221.

5: Kaliner MA, Oppenheimer J, Farrar JR. Comprehensive review of olopatadine: the molecule and its clinical entities. Allergy Asthma Proc. 2010 Mar-Apr;31(2):112-9. doi: 10.2500/aap.2010.31.3317. Review. PubMed PMID: 20406593.

6: Kaliner MA. Azelastine and olopatadine in the treatment of allergic rhinitis. Ann Allergy Asthma Immunol. 2009 Nov;103(5):373-80. doi: 10.1016/S1081-1206(10)60355-9. Review. PubMed PMID: 19927534.

7: Watanabe M, Kodama H, Hasegawa K, Itoh K. [Pharmacological profile and clinical efficacy of olopatadine hydrochloride ophthalmic solution (Patanol 0.1% ophthalmic solution)]. Nihon Yakurigaku Zasshi. 2007 Sep;130(3):221-31. Review. Japanese. PubMed PMID: 17878619.

8: Rosenwasser LJ, O'Brien T, Weyne J. Mast cell stabilization and anti-histamine effects of olopatadine ophthalmic solution: a review of pre-clinical and clinical research. Curr Med Res Opin. 2005 Sep;21(9):1377-87. Review. PubMed PMID: 16197656.

9: Abelson MB. A review of olopatadine for the treatment of ocular allergy. Expert Opin Pharmacother. 2004 Sep;5(9):1979-94. Review. PubMed PMID: 15330735.

10: Ohmori K, Hayashi K, Kaise T, Ohshima E, Kobayashi S, Yamazaki T, Mukouyama A. Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride, a new antiallergic drug. Jpn J Pharmacol. 2002 Apr;88(4):379-97. Review. PubMed PMID: 12046981.

11: Abelson MB, Gomes PJ. Olopatadine 0.2% ophthalmic solution: the first ophthalmic antiallergy agent with once-daily dosing. Expert Opin Drug Metab Toxicol. 2008 Apr;4(4):453-61. doi: 10.1517/17425255.4.4.453 . Review. PubMed PMID: 18433347.

12: McGill JI. A review of the use of olopatadine in allergic conjunctivitis. Int Ophthalmol. 2004 May;25(3):171-9. Review. PubMed PMID: 15847317.

13: Ohmori K, Hasegawa K, Tamura T, Miyake K, Matsubara M, Masaki S, Karasawa A, Urayama N, Horikoshi K, Kajita J, Hasegawa M, Taniguchi K, Komada T, Kawamoto Y. Properties of olopatadine hydrochloride, a new antiallergic/antihistaminic drug. Arzneimittelforschung. 2004;54(12):809-29. Review. PubMed PMID: 15646365.

14: Bielory L, Buddiga P, Bigelson S. Ocular allergy treatment comparisons: azelastine and olopatadine. Curr Allergy Asthma Rep. 2004 Jul;4(4):320-5. Review. PubMed PMID: 15175148.

15: Ohmori K, Ikemura T, Kobayashi H, Mukouyama A. [Pharmacological, pharmacokinetic and clinical properties of olopatadine hydrochloride' (olopatadine), an antiallergic drug]. Nihon Yakurigaku Zasshi. 2001 Jul;118(1):51-8. Review. Japanese. PubMed PMID: 11496828.