Bufexamac

Bufexamac

Systematic (IUPAC) name
2-(4-butoxyphenyl)-N-hydroxyacetamide
Clinical data
AHFS/Drugs.com	International Drug Names
Legal status	OTC
Routes of administration	Topical, rectal
Pharmacokinetic data
Excretion	Renal
Identifiers
CAS Number	2438-72-4
ATC code	M01AB17 (WHO) M02AA09
PubChem	CID: 2466
IUPHAR/BPS	7498
ChemSpider	2372
UNII	4T3C38J78L Y
KEGG	D01271
ChEMBL	CHEMBL94394
Chemical data
Formula	C12H17NO3
Molecular mass	223.268 g/mol
SMILES ONC(=O)Cc1ccc(OCCCC)cc1
InChI 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) Key:MXJWRABVEGLYDG-UHFFFAOYSA-N

Bufexamac is a drug used as an anti-inflammatory agent on the skin, as well as rectally. Common brand names include Paraderm and Parfenac. It was withdrawn in Europe because of allergic reactions.

Indications

Ointments and lotions containing bufexamac are used for the treatment of subacute and chronic eczema of the skin, including atopic eczema, as well as sunburn and other minor burns, and itching. Suppositories containing bufexamac in combination with local anaesthetics are used against haemorrhoids.

Pharmacology

Bufexamac is thought to act by inhibiting the enzyme cyclooxygenase, which would make it a non-steroidal anti-inflammatory drug. Evidence on the mechanism of action is scarce. Furthermore, bufexamac was identified as a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10).

Side effects

Bufexamac can cause severe contact dermatitis which is often hard to distinguish from the initial condition. As a consequence, the European Medicines Agency recommended to withdraw the marketing approval in April 2010.