bufexamac
{{Short description|Chemical compound}}
{{Infobox drug
| IUPAC_name = 2-(4-butoxyphenyl)-N-hydroxyacetamide
| image = Bufexamac Structural Formula V2.svg
| image_class = skin-invert-image
| tradename =
| Drugs.com = {{drugs.com|international|bufexamac}}
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = OTC
| routes_of_administration = Topical, rectal
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion = Renal
| IUPHAR_ligand = 7498
| CAS_number = 2438-72-4
| ATC_prefix = M01
| ATC_suffix = AB17
| ATC_supplemental = {{ATC|M02|AA09}}
| PubChem = 2466
| DrugBank =
| ChEMBL = 94394
| ChemSpiderID = 2372
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4T3C38J78L
| KEGG = D01271
| C=12 | H=17 | N=1 | O=3
| smiles = ONC(=O)Cc1ccc(OCCCC)cc1
| StdInChI=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)
| StdInChIKey = 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 It was withdrawn in Europe and Australia{{cite journal|url=https://www.tga.gov.au/alert/bufexamac|title=Bufexamac Safety advisory - risk of serious skin reactions|journal=Therapeutic Goods Administration |year=2020}} 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|date=May 2010}} and itching. Suppositories containing bufexamac in combination with local anaesthetics are used against haemorrhoids.{{cite book | title=Arzneistoff-Profile| veditors = Dinnendahl V, Fricke U |publisher=Govi Pharmazeutischer Verlag|location=Eschborn, Germany |year=2010 |edition=23 |volume=2 |isbn=978-3-7741-9846-3 |language=German }}
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.{{cite book | vauthors = Gloor M, Thoma K, Fluhr J |title=Dermatologische Externatherapie: Unter besonderer Berücksichtigung der Magistralrezeptur |language=German |publisher=Springer |year=2000 |isbn=978-3-540-67174-9 |page=349 }}
Furthermore, bufexamac was identified as a specific inhibitor of class IIB histone deacetylases (HDAC6 and HDAC10).{{cite journal | vauthors = Bantscheff M, Hopf C, Savitski MM, Dittmann A, Grandi P, Michon AM, Schlegl J, Abraham Y, Becher I, Bergamini G, Boesche M, Delling M, Dümpelfeld B, Eberhard D, Huthmacher C, Mathieson T, Poeckel D, Reader V, Strunk K, Sweetman G, Kruse U, Neubauer G, Ramsden NG, Drewes G | display-authors = 6 | title = Chemoproteomics profiling of HDAC inhibitors reveals selective targeting of HDAC complexes | journal = Nature Biotechnology | volume = 29 | issue = 3 | pages = 255–265 | date = March 2011 | pmid = 21258344 | doi = 10.1038/nbt.1759 | s2cid = 205275159 }}
Side effects
Bufexamac can cause severe contact dermatitis which is often hard to distinguish from the initial condition.{{cite journal|url=http://www.akdae.de/Arzneimittelsicherheit/Bekanntgaben/Archiv/2000/20001124.html|title=Bufexamac: Ein Ekzemtherapeutikum, das selbst häufig allergische Kontaktekzeme hervorruft|language=German|journal=Deutsches Ärzteblatt|issue=47|year=2000}} As a consequence, the European Medicines Agency recommended to withdraw the marketing approval in April 2010.{{cite news|publisher=European Medicines Agency|title=European Medicines Agency recommends revocation of marketing authorisations for bufexamac|url=http://www.ema.europa.eu/pdfs/human/referral/bufexamac/24639510en.pdf|date=2010-04-22|access-date=2010-05-01|archive-date=2010-05-31|archive-url=https://web.archive.org/web/20100531002435/http://www.ema.europa.eu/pdfs/human/referral/bufexamac/24639510en.pdf|url-status=dead}}
References
{{reflist}}
{{Anti-inflammatory and antirheumatic products}}
{{Topical products for joint and muscular pain}}
{{Prostanoidergics}}