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Details

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
Structure of BUFEXAMAC

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)

HIDE SMILES / InChI

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

Description

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.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
10.7 µM [Kd]
12.3 µM [Kd]
15.86 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BUFEXAMAC
Primary
BUFEXAMAC
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Apply 5% cream to affected areas.
Route of Administration: Topical
In Vitro Use Guide
Treatment of peripheral blood mononuclear cells with bufexamac inhibits the secretion of IFN-α (EC50 = 8.9 uM)
Substance Class Chemical
Record UNII
4T3C38J78L
Record Status Validated (UNII)
Record Version