Stereochemistry | ACHIRAL |
Molecular Formula | C12H17NO3 |
Molecular Weight | 223.2683 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCOC1=CC=C(CC(=O)NO)C=C1
InChI
InChIKey=MXJWRABVEGLYDG-UHFFFAOYSA-N
InChI=1S/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)
Molecular Formula | C12H17NO3 |
Molecular Weight | 223.2683 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Bufexamac is a nonsteroidal antiinflammatory drug (NSAID) used in topical formulations to treat dermatological diseases (eczema and dermatitis) and proctological conditions (haemorrhoids and anal fissure). Bufexamac-containing medicines have been available in EU Member States since the 1970s. In 2010 European Medicines Agency recommends revocation of marketing authorisations for bufexamac due to high risk of contact allergies. The phenolic bufexamac decomposition products could be the reason for its eczema-provoking properties frequently described in the literature. Bufexamac is a class IIb histone deacetylase (HDAC6, HDAC10) inhibitor. Bufexamac also triggered an HDAC6-independent, hypoxia-like response by stabilizing Hypoxia-inducible factor 1-alpha, providing a possible mechanistic explanation of its adverse, pro-inflammatory effects. Bufexamac was capable of specifically inhibiting leukotriene A4 hydrolase and attenuating lung inflammation in acute lung injury mouse model.