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Bufexamac

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Bufexamac
File: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 7pxY
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 It was withdrawn in Europe because of allergic reactions.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

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

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

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

  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. PMID 21258344. doi:10.1038/nbt.1759. 
  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.