348622-88-8

Basic information

• Product Name: 3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide
• Synonyms: 1,2,4-Oxadiazole-5-propanamide, 3-(aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-, (βR)-;(βR)-3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide;3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide;UK 383367;5-[(1R)-4-Cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl]-1,2,4-oxadiazole-3-carboxamide
• CAS NO: 348622-88-8
• Molecular Formula: C15H24N4O4
• Molecular Weight: 324.37546
• Product Categories: Inhibitors
• Mol File: 348622-88-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 136-138℃
• Appearance: white to off-white/
• Density: 1.233
• Storage Temp.: Store at -20°C
• Solubility: DMSO: >30mg/mL
• PKA: 9.03±0.20(Predicted)
• CAS DataBase Reference: 3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide(348622-88-8)
• EPA Substance Registry System: 3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide(348622-88-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 348622-88-8(Hazardous Substances Data)

Usage

Uses

Potent and selective nonpeptidic inhibitor of procollagen C-proteinase (PCP) inhibitor. A potential dermal anti-scarring agent.

Biological Activity

uk 383367 is a novel procollagen c-protein (pcp) inhibitor being investigated for the treatment of post-surgical dermal scarring, which potently inhibits the activity of pcp with the value of 50% inhibition concentration ic50 of 44 nm, as well as a selective inhibitor of matrix metalloproteinases (mmps) with values of ic50 >60,000 nm for mmp-2 and >10,000 nm for mmp-1, mmp-3, mmp-9 and mmp-4. although the mechanism is not clear yet, uk 383367 also exhibits weak inhibitory effects against phosphodiesterase-4 (pde-4) enzyme, including pde-4a, pde-4b, pde-4c and pde-4d, with values of ic50 of 1.8 μm, 1.5 μm, 2.4 μm and 0.9 μm respectively.g. a. allan, j. i. gedge, a. n. r. nedderman, s. j. roffey, h. f. small and r. webster. pharmacokinetics and metabolism of uk-383,367 in rats and dogs: a rationale for long-lived plasma radioactivity. xenobiotica 2006; 36(5): 399-418bailey s, fish pv, billotte s, bordner j, greiling d, james k, mcelroy a, mills je, reed c, webster r.ff. succinyl hydroxamates as potent and selective non-peptidic inhibitors of procollagen c-proteinase: design, synthesis, and evaluation as topically applied, dermal anti-scarring agents. bioorg med chem lett. 2008;18(24):6562-6567

Upstream product

• 348622-98-0 ethyl 5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl)-1,2,4-oxadiazole-3-carboxylate 

Relevant articles and documents

Succinyl hydroxamates as potent and selective non-peptidic inhibitors of procollagen C-proteinase: Design, synthesis, and evaluation as topically applied, dermal anti-scarring agents

Succinyl hydroxamates 1 and 2 are disclosed as novel series of potent and selective inhibitors of procollagen C-proteinase (PCP) which may have potential as anti-fibrotic agents. Carboxamide 7 demonstrated good PCP inhibition and had excellent selectivity