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 It was withdrawn in Europe and Australia[1] because of allergic reactions.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.comInternational Drug Names
Routes of
administration		Topical, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
ExcretionRenal
Identifiers
IUPAC name
  • 2-(4-butoxyphenyl)-N-hydroxyacetamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.017.683
Chemical and physical data
FormulaC12H17NO3
Molar mass223.272 g·mol−1
3D model (JSmol)
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, 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
  1. "Bufexamac Safety advisory - risk of serious skin reactions". Therapeutic Goods Administration (TGA). 2020.
  2. Dinnendahl V, Fricke U, eds. (2010). Arzneistoff-Profile (in German). Vol. 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
  3. Gloor M, Thoma K, Fluhr J (2000). Dermatologische Externatherapie: Unter besonderer Berücksichtigung der Magistralrezeptur (in German). Springer. p. 349. ISBN 978-3-540-67174-9.
  4. Bantscheff M, Hopf C, Savitski MM, Dittmann A, Grandi P, Michon AM, et al. (March 2011). "Chemoproteomics profiling of HDAC inhibitors reveals selective targeting of HDAC complexes". Nature Biotechnology. 29 (3): 255–65. doi:10.1038/nbt.1759. PMID 21258344. S2CID 205275159.
  5. "Bufexamac: Ein Ekzemtherapeutikum, das selbst häufig allergische Kontaktekzeme hervorruft". Deutsches Ärzteblatt (in German) (47). 2000.
  6. "European Medicines Agency recommends revocation of marketing authorisations for bufexamac" (PDF). European Medicines Agency. 2010-04-22.
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