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

MedKoo CAT#: 319812

CAS#: 887375-26-0

Description: Mapracorat, also known as BOL-303242-X and ZK-245186, is an selective glucocorticoid receptor agonists (SEGRAs) under clinical trials for the topical treatment of atopic dermatitis, inflammation following cataract surgery, and allergic conjunctivitis. Mapracorat inhibits hyperosmolar-induced cytokine release and MAPK pathways in human corneal epithelial cells.


Price and Availability

Size
Price

1g
USD 5950
Size
Price

2g
USD 9650
Size
Price

5g
USD 15850

Mapracorat, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319812
Name: Mapracorat
CAS#: 887375-26-0
Chemical Formula: C25H26F4N2O2
Exact Mass: 462.193
Molecular Weight: 462.4886
Elemental Analysis: C, 64.93; H, 5.67; F, 16.43; N, 6.06; O, 6.92


Synonym: ZK-245186; ZK 245186; ZK245186; BOL-303242; BOL303242; BOL 303242; BOL-303242-X; Mapracorat

IUPAC/Chemical Name: (2R)-1,1,1-trifluoro-4-(5-fluoro-2,3-dihydro-1-benzofuran-7-yl)-4-methyl-2-[[(2-methylquinolin-5-yl)amino]methyl]pentan-2-ol

InChi Key: VJGFOYBQOIPQFY-XMMPIXPASA-N

InChi Code: InChI=1S/C25H26F4N2O2/c1-15-7-8-18-20(5-4-6-21(18)31-15)30-14-24(32,25(27,28)29)13-23(2,3)19-12-17(26)11-16-9-10-33-22(16)19/h4-8,11-12,30,32H,9-10,13-14H2,1-3H3/t24-/m1/s1

SMILES Code: CC(C)(C1=CC(F)=CC2=C1OCC2)C[C@@](O)(CNC3=C4C=CC(C)=NC4=CC=C3)C(F)(F)F


Technical Data

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).

Harmonized System Code:
293490


References

1: Baiula M, Spampinato S. Mapracorat, a novel non-steroidal selective glucocorticoid receptor agonist for the treatment of allergic conjunctivitis. Inflamm Allergy Drug Targets. 2014;13(5):289-98. Review. PubMed PMID: 25373600.

2: Spinelli SL, Xi X, McMillan DH, Woeller CF, Richardson ME, Cavet ME, Zhang JZ, Feldon SE, Phipps RP. Mapracorat, a selective glucocorticoid receptor agonist, upregulates RelB, an anti-inflammatory nuclear factor-kappaB protein, in human ocular cells. Exp Eye Res. 2014 Oct;127:290-8. doi: 10.1016/j.exer.2014.07.013. PubMed PMID: 25245083.

3: Baiula M, Bedini A, Baldi J, Cavet ME, Govoni P, Spampinato S. Mapracorat, a selective glucocorticoid receptor agonist, causes apoptosis of eosinophils infiltrating the conjunctiva in late-phase experimental ocular allergy. Drug Des Devel Ther. 2014 Jun 10;8:745-57. doi: 10.2147/DDDT.S62659. eCollection 2014. PubMed PMID: 24959069; PubMed Central PMCID: PMC4061172.

4: Cavet ME, Volhejn S, Harrington KL, Zhang JZ. Anti-allergic effects of mapracorat, a novel selective glucocorticoid receptor agonist, in human conjunctival fibroblasts and epithelial cells. Mol Vis. 2013 Jul 19;19:1515-25. Print 2013. PubMed PMID: 23878502; PubMed Central PMCID: PMC3716413.

5: Vollmer TR, Stockhausen A, Zhang JZ. Anti-inflammatory effects of mapracorat, a novel selective glucocorticoid receptor agonist, is partially mediated by MAP kinase phosphatase-1 (MKP-1). J Biol Chem. 2012 Oct 12;287(42):35212-21. doi: 10.1074/jbc.M112.400671. Epub 2012 Aug 16. PubMed PMID: 22898817; PubMed Central PMCID: PMC3471745.

6: Lan W, Petznick A, Heryati S, Rifada M, Tong L. Nuclear Factor-κB: central regulator in ocular surface inflammation and diseases. Ocul Surf. 2012 Jul;10(3):137-48. doi: 10.1016/j.jtos.2012.04.001. Epub 2012 Apr 30. Review. PubMed PMID: 22814642.

7: Baiula M, Spartà A, Bedini A, Carbonari G, Bucolo C, Ward KW, Zhang JZ, Govoni P, Spampinato S. Eosinophil as a cellular target of the ocular anti-allergic action of mapracorat, a novel selective glucocorticoid receptor agonist. Mol Vis. 2011;17:3208-23. Epub 2011 Dec 14. PubMed PMID: 22194647; PubMed Central PMCID: PMC3244483.

8: Joanny E, Ding Q, Gong L, Kong P, Saklatvala J, Clark AR. Anti-inflammatory effects of selective glucocorticoid receptor modulators are partially dependent on up-regulation of dual specificity phosphatase 1. Br J Pharmacol. 2012 Feb;165(4b):1124-36. doi: 10.1111/j.1476-5381.2011.01574.x. PubMed PMID: 21718312; PubMed Central PMCID: PMC3346253.

9: Proksch JW, Lowe ER, Ward KW. Ocular pharmacokinetics of mapracorat, a novel, selective glucocorticoid receptor agonist, in rabbits and monkeys. Drug Metab Dispos. 2011 Jul;39(7):1181-7. doi: 10.1124/dmd.111.039099. Epub 2011 Mar 25. PubMed PMID: 21441467.

10: Shafiee A, Bucolo C, Budzynski E, Ward KW, López FJ. In vivo ocular efficacy profile of mapracorat, a novel selective glucocorticoid receptor agonist, in rabbit models of ocular disease. Invest Ophthalmol Vis Sci. 2011 Mar 14;52(3):1422-30. doi: 10.1167/iovs.10-5598. PubMed PMID: 20881303.

11: Cavet ME, Harrington KL, Ward KW, Zhang JZ. Mapracorat, a novel selective glucocorticoid receptor agonist, inhibits hyperosmolar-induced cytokine release and MAPK pathways in human corneal epithelial cells. Mol Vis. 2010 Sep 2;16:1791-800. PubMed PMID: 20824100; PubMed Central PMCID: PMC2932489.

12: Zhang JZ, Cavet ME, VanderMeid KR, Salvador-Silva M, López FJ, Ward KW. BOL-303242-X, a novel selective glucocorticoid receptor agonist, with full anti-inflammatory properties in human ocular cells. Mol Vis. 2009 Dec 8;15:2606-16. PubMed PMID: 20011631; PubMed Central PMCID: PMC2790480.

13: Pfeffer BA, DeWitt CA, Salvador-Silva M, Cavet ME, López FJ, Ward KW. Reduced myocilin expression in cultured monkey trabecular meshwork cells induced by a selective glucocorticoid receptor agonist: comparison with steroids. Invest Ophthalmol Vis Sci. 2010 Jan;51(1):437-46. doi: 10.1167/iovs.09-4202. Epub 2009 Aug 20. PubMed PMID: 19696178.

14: Schäcke H, Zollner TM, Döcke WD, Rehwinkel H, Jaroch S, Skuballa W, Neuhaus R, May E, Zügel U, Asadullah K. Characterization of ZK 245186, a novel, selective glucocorticoid receptor agonist for the topical treatment of inflammatory skin diseases. Br J Pharmacol. 2009 Oct;158(4):1088-103. doi: 10.1111/j.1476-5381.2009.00238.x. Epub 2009 May 6. PubMed PMID: 19422381; PubMed Central PMCID: PMC2785530.