Bufexamac

Bufexamac

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Topical, rectal
ATC code	M01AB17 (WHO) M02AA09 (WHO)
Legal status
Legal status	OTC
Pharmacokinetic data
Excretion	Renal
Identifiers
IUPAC name 2-(4-butoxyphenyl)-N-hydroxyacetamide
CAS Number	2438-72-4
PubChem (CID)	2466
IUPHAR/BPS	7498
ChemSpider	2372
UNII	4T3C38J78L
KEGG	D01271
ChEMBL	CHEMBL94394
ECHA InfoCard	100.017.683
Chemical and physical data
Formula	C12H17NO3
Molar mass	223.268 g/mol
3D model (Jmol)	Interactive image
SMILES ONC(=O)Cc1ccc(OCCCC)cc1
InChI 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 It was withdrawn in Europe because of allergic reactions.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, 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]

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, eds. (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.