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MedKoo Cat#: 319812 | Name: Mapracorat
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Description:

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

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.

Chemical Structure

Mapracorat
Mapracorat
CAS#887375-26-0

Theoretical Analysis

MedKoo Cat#: 319812

Name: Mapracorat

CAS#: 887375-26-0

Chemical Formula: C25H26F4N2O2

Exact Mass: 462.1930

Molecular Weight: 462.49

Elemental Analysis: C, 64.93; H, 5.67; F, 16.43; N, 6.06; O, 6.92

Price and Availability

Size Price Availability Quantity
5mg USD 895.00 2 Weeks
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Related CAS #
No Data
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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 462.49 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
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. doi: 10.2174/1871528113666141106101356. 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. 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. PMID: 24959069; PMCID: PMC4061172. 4: 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. PMID: 20824100; PMCID: PMC2932489. 5: 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. PMID: 21441467. 6: Bäumer W, Rossbach K, Schmidt BH. The selective glucocorticoid receptor agonist mapracorat displays a favourable safety-efficacy ratio for the topical treatment of inflammatory skin diseases in dogs. Vet Dermatol. 2017 Feb;28(1):46-e11. doi: 10.1111/vde.12315. Epub 2016 Jul 18. PMID: 27425245. 7: 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):35212-35221. doi: 10.1074/jbc.M112.400671. Epub 2012 Aug 16. PMID: 22898817; PMCID: PMC3471745. 8: 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. PMID: 23878502; PMCID: PMC3716413. 9: 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. PMID: 22194647; PMCID: PMC3244483. 10: 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. PMID: 22814642. 11: Wigger-Alberti W, Williams R, von Mackensen YL, Hoffman-Wecker M, Grossmann U, Staedtler G, Nkulikiyinka R, Shakery K. Comparison of Occlusive and Open Application in a Psoriasis Plaque Test Design, Exemplarily Using Investigations of Mapracorat 0.1% Ointment versus Vehicle and Reference Drugs. Skin Pharmacol Physiol. 2017;30(2):102-114. doi: 10.1159/000458415. Epub 2017 Apr 14. PMID: 28407625. 12: 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. PMID: 20881303. 13: 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. PMID: 21718312; PMCID: PMC3346253. 14: 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. PMID: 20011631; PMCID: PMC2790480. 15: 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. PMID: 19422381; PMCID: PMC2785530. 16: 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. PMID: 19696178.