Bufexamac

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 It was withdrawn in Europe and Australia^[1] because of allergic reactions.

Bufexamac

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical, rectal
ATC code	M01AB17 (WHO) M02AA09 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
Pharmacokinetic data
Excretion	Renal
Identifiers
IUPAC name 2-(4-butoxyphenyl)-N-hydroxyacetamide
CAS Number	2438-72-4
PubChem CID	2466
IUPHAR/BPS	7498
ChemSpider	2372
UNII	4T3C38J78L
KEGG	D01271
ChEMBL	ChEMBL94394
CompTox Dashboard (EPA)	DTXSID7045368
ECHA InfoCard	100.017.683
Chemical and physical data
Formula	C12H17NO3
Molar mass	223.272 g·mol−1
3D model (JSmol)	Interactive image
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

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,^{[citation needed]} and itching. Suppositories containing bufexamac in combination with local anaesthetics are used against haemorrhoids.^[2]

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.^[3] Furthermore, bufexamac was identified as a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10).^[4]

Side effects

Bufexamac can cause severe contact dermatitis which is often hard to distinguish from the initial condition.^[5] As a consequence, the European Medicines Agency recommended to withdraw the marketing approval in April 2010.^[6]