Bufexamac

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Bufexamac
Bufexamac Structural Formula V.1.svg
Systematic (IUPAC) name
2-(4-butoxyphenyl)-N-hydroxyacetamide
Clinical data
AHFS/Drugs.com International Drug Names
  • OTC
Topical, rectal
Pharmacokinetic data
Excretion Renal
Identifiers
2438-72-4
M01AB17 M02AA09
PubChem CID 2466
ChemSpider 2372
UNII 4T3C38J78L YesY
ChEMBL CHEMBL94394
Chemical data
Formula C12H17NO3
223.268 g/mol

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 It was withdrawn in Europe because of allergic reactions.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[edit]

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.[1]

Pharmacology[edit]

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.[2] Furthermore, bufexamac was identified as a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10),[3] which may contribute to its clinical efficacy.[citation needed]

Side effects[edit]

Bufexamac can cause severe contact dermatitis which is often hard to distinguish from the initial condition.[4] As a consequence, the European Medicines Agency recommended to withdraw the marketing approval in April 2010.[5]

References[edit]

  1. ^ Dinnendahl, V, Fricke, U, ed. (2010). Arzneistoff-Profile (in German) 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3. 
  2. ^ Gloor, Max; Thoma, Karl; Fluhr, Joachim (2000). Dermatologische Externatherapie: Unter besonderer Berücksichtigung der Magistralrezeptur (in German). Springer. p. 349. ISBN 3-540-67174-9. 
  3. ^ Bantscheff, Marcus; Hopf, Carsten; Savitski, Mikhail M; Dittmann, Antje; Grandi, Paola; Michon, Anne-Marie; Schlegl, Judith; Abraham, Yann; Becher, Isabelle; Bergamini, Giovanna; Boesche, Markus; Delling, Manja; Dümpelfeld, Birgit; Eberhard, Dirk; Huthmacher, Carola; Mathieson, Toby; Poeckel, Daniel; Reader, Valérie; Strunk, Katja; Sweetman, Gavain; Kruse, Ulrich; Neubauer, Gitte; Ramsden, Nigel G; Drewes, Gerard (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. 
  4. ^ "Bufexamac: Ein Ekzemtherapeutikum, das selbst häufig allergische Kontaktekzeme hervorruft". Deutsches Ärzteblatt (in German) (47). 2000. 
  5. ^ "European Medicines Agency recommends revocation of marketing authorisations for bufexamac" (PDF). European Medicines Agency. 2010-04-22.