SML4342

MMF prodrug-1c

≥95% (HPLC)

• Synonym(s): (E)-4-Oxo-pent-2-enedioic acid dimethyl ester, 1,5-Dimethyl (2E)-4-oxopent-2-enedioate; (E)-Dimethyl 4-oxopent-2-enedioate, Monomethyl fumarate Prodrug-1c, NRF2 Activator, MMF Prodrug-1c, NFE2L2 Activator MMF, Prodrug-1c
• Empirical Formula (Hill Notation): C₇H₈O₅
• CAS Number: 38256-25-6
• Molecular Weight: 172.14
• MDL number: MFCD00042934
• UNSPSC Code: 12352203
• Assay: ≥95% (HPLC)
• Form: powder

Properties

• Quality Segment: 100
• assay: ≥95% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: 2-8°C

Description

Biochem/physiol Actions

MMF prodrug-1c is a cell permeable activator of NRF2. A site-specific monomethyl fumarate (MMF) prodrug (1c) achieves targeted delivery of MMF through a peroxide-dependent Baeyer-Villiger oxidation mechanism, selectively activating NRF2 at sites of pathological oxidative stress. Upon oral administration, MMF prodrug-1c rapidly converts to a stable glutathione S-conjugate that circulates until encountering elevated peroxide concentrations (>1 μM H2O2 or >20 μM peroxynitrite) at disease sites, where it releases therapeutic MMF while avoiding indiscriminate NRF2 activation in healthy tissues. At an optimal dose of 350 μmol/kg/day, MMF prodrug-1c demonstrates superior efficacy to conventional MMF delivery in multiple chronic pain models, reversing peripheral neuropathy, osteoarthritis, and chemotherapy-induced neuropathic pain without inducing systemic side effects like glutathione depletion or cutaneous flushing.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Codes: H317,H319
• Precautionary Statements: P261 - P264 - P272 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable