Mapracorat

{{Short description|Type of selective glucocorticoid receptor agonist}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 406275524

| IUPAC_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

| image = Mapracorat_skeletal.svg

| width = 250

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status = Investigational

| routes_of_administration = Topical (ointment, eye drops)

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 887375-26-0

| ATC_prefix = none

| ATC_suffix =

| ATC_supplemental =

| PubChem = 24795088

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| KEGG = D10136

| KEGG_Ref = {{keggcite|changed|kegg}}

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 25104194

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 145V79YBVP

| chemical_formula =

| C=25 | H=26 | F=4 | N=2 | O=2

| smiles = c14OCCc4cc(F)cc1C(C)(C)CC(O)(C(F)(F)F)CNc(cccc2n3)c2ccc3C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VJGFOYBQOIPQFY-XMMPIXPASA-N

}}

Mapracorat (INN, code names BOL-303242-X, ZK-245186{{cite journal | vauthors = Cavet ME, Harrington KL, Ward KW, Zhang JZ | title = Mapracorat, a novel selective glucocorticoid receptor agonist, inhibits hyperosmolar-induced cytokine release and MAPK pathways in human corneal epithelial cells | journal = Molecular Vision | volume = 16 | pages = 1791–800 | date = September 2010 | pmid = 20824100 | pmc = 2932489 }}) is an anti-inflammatory drug belonging to the experimental class of selective glucocorticoid receptor agonists (SEGRAs). It is in clinical trials for the topical treatment of atopic dermatitis,{{ClinicalTrialsGov|NCT00944632|Dose Escalation of Different Concentrations of ZK 245186 in Atopic Dermatitis}} inflammation following cataract surgery,{{ClinicalTrialsGov|NCT00905450|Evaluation of BOL-303242-X Versus Vehicle for the Treatment of Inflammation Following Cataract Surgery}} and allergic conjunctivitis.{{ClinicalTrialsGov|NCT01289431|Mapracorat Ophthalmic Formulation in Subjects With Allergic Conjunctivitis}} Preliminary investigation for the treatment of keratoconjunctivitis sicca has been conducted in cellular models.

Clinical trials

Phase II clinical trials with mapracorat started in summer 2009. One trial was a double blind dose finding study for an ointment against atopic dermatitis. It tested concentrations of 0.01%, 0.03% and 0.1% versus placebo over four weeks in around 64 patients. This trial was conducted by Intendis, a part of Bayer HealthCare Pharmaceuticals specialized on dermatology, and completed in September or October 2010. The other trial, also with a double blind design, evaluated an ophthalmic suspension for the treatment of inflammation following cataract surgery. Various concentrations and dosing schemes were tested versus placebo in about 550 patients. The study was conducted by Bausch & Lomb and completed in September 2010. Its successor study, a phase III trial, started in November 2010 and completed in August 2011.{{ClinicalTrialsGov|NCT01230125|Mapracorat Ophthalmic Suspension for the Treatment of Ocular Inflammation Following Cataract Surgery}}

{{as of|2017|1}} no study results are available.

See also

References

{{Reflist|2}}

{{Glucocorticoids and antiglucocorticoids}}

{{Glucocorticoid receptor modulators}}

Category:Anti-inflammatory agents

Category:Benzofurans

Category:Fluoroarenes

Category:Immunosuppressants

Category:Quinolines

Category:Selective glucocorticoid receptor modulators

Category:Trifluoromethyl compounds

{{musculoskeletal-drug-stub}}

{{antineoplastic-drug-stub}}

{{dermatologic-drug-stub}}