Monomethyl fumarate

Monomethyl fumarate is an active metabolite of the immune modulator dimethyl fumarate (Cay-14714) that is rapidly formed from dimethyl fumarate by hydrolysis. It is an agonist of the hydroxycarboxylic acid 2 (HCA2) receptor/GPR109A with an EC50 value of 9.4 µM for inducing calcium accumulation in CHO cells expressing the receptor. Monomethyl fumarate reduces neutrophil adhesion to endothelial cells stimulated with TNF, decreases CXCL2-directed neutrophil migration, and increases the expression of the Nrf2 target gene NQO1 in wild-type but not HCA2-/- macrophages. It inhibits proliferation and induces differentiation in keratinocytes, as well as decreases the levels of TNF-alpha induced by phorbol 12-myristate 13-acetate (TPA, Cay-10008014) in keratinocytes when used at a concentration of 1 mM. Monomethyl fumarate (1 mg/day) reduces symptoms of experimental autoimmune encephalomyelitis (EAE) in mice and isolated natural killer cells from these mice induced cytotoxicity in previously isolated immature and mature dendritic cells. Formulations containing monomethyl fumarate have been used in the treatment of multiple sclerosis.Formal Name: 2E-butenedioic acid, 1-methyl ester. CAS Number: 2756-87-8. Synonyms: Fumaric Acid monomethyl ester. Molecular Formula: C5H6O4. Formula Weight: 130.1. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: 0.5 mg/ml, PBS (pH 7.2): 1 mg/ml. SMILES: OC(/C=C/C(OC)=O)=O. InChi Code: InChI=1S/C5H6O4/c1-9-5(8)3-2-4(6)7/h2-3H,1H3,(H,6,7)/b3-2+. InChi Key: NKHAVTQWNUWKEO-NSCUHMNNSA-N.