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Bufexamac

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.017.683Edit 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

Bufexamac is a drug used as ananti-inflammatory agent on the skin, as well asrectally. Common brand names includeParaderm andParfenac. It was withdrawn in Europe and Australia[1] because of allergic reactions.

Indications

[edit]

Ointments and lotions containing bufexamac are used for the treatment of subacute and chroniceczema of the skin, includingatopic eczema, as well assunburn and other minor burns,[citation needed] anditching.Suppositories containing bufexamac in combination withlocal anaesthetics are used againsthaemorrhoids.[2]

Pharmacology

[edit]

Bufexamac is thought to act by inhibiting the enzymecyclooxygenase, which would make it anon-steroidal anti-inflammatory drug. Evidence on the mechanism of action is scarce.[3]Furthermore, bufexamac was identified as a specific inhibitor of class IIBhistone deacetylases (HDAC6 andHDAC10).[4]

Side effects

[edit]

Bufexamac can cause severecontact dermatitis which is often hard to distinguish from the initial condition.[5] As a consequence, theEuropean Medicines Agency recommended to withdraw the marketing approval in April 2010.[6]

References

[edit]
  1. ^"Bufexamac Safety advisory - risk of serious skin reactions".Therapeutic Goods Administration. 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 fromthe original(PDF) on 2010-05-31. Retrieved2010-05-01.
pyrazolones /
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Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
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