Bufexamac

Chemical compound From Wikipedia, the free encyclopedia

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 It was withdrawn in Europe and Australia[1] because of allergic reactions.

ATC code
Legal status
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Bufexamac
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Topical, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
ExcretionRenal
Identifiers
  • 2-(4-butoxyphenyl)-N-hydroxyacetamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.017.683 Edit this at Wikidata
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
  • ONC(=O)Cc1ccc(OCCCC)cc1
  • 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
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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]

References

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