Bufexamac

Last updated
Bufexamac
Bufexamac Structural Formula V2.svg
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration
Topical, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Excretion Renal
Identifiers
  • 2-(4-butoxyphenyl)-N-hydroxyacetamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.017.683 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C12H17NO3
Molar mass 223.272 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

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 It was withdrawn in Europe and Australia [1] because of allergic reactions.

Contents

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]

Related Research Articles

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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): 255–265. 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. Archived from the original (PDF) on 2010-05-31. Retrieved 2010-05-01.