Bufexamac
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| Systematic (IUPAC) name | |
|---|---|
| 2-(4-butoxyphenyl)-N-hydroxyacetamide | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
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| Topical, rectal | |
| Pharmacokinetic data | |
| Excretion | Renal |
| Identifiers | |
| 2438-72-4 | |
| M01AB17 M02AA09 | |
| PubChem | CID 2466 |
| ChemSpider | 2372 |
| UNII |
4T3C38J78L  |
| ChEMBL | CHEMBL94394 |
| Chemical data | |
| Formula | C12H17NO3 |
| 223.268 g/mol | |
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SMILES
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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 It was withdrawn in Europe because of allergic reactions.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] which may contribute to its clinical efficacy.
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
- ↑ Dinnendahl, V, Fricke, U, ed. (2010). Arzneistoff-Profile (in German) 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
- ↑ Gloor, Max; Thoma, Karl; Fluhr, Joachim (2000). Dermatologische Externatherapie: Unter besonderer Berücksichtigung der Magistralrezeptur (in German). Springer. p. 349. ISBN 3-540-67174-9.
- ↑ 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.
- ↑ "Bufexamac: Ein Ekzemtherapeutikum, das selbst häufig allergische Kontaktekzeme hervorruft". Deutsches Ärzteblatt (in German) (47). 2000.
- ↑ "European Medicines Agency recommends revocation of marketing authorisations for bufexamac". European Medicines Agency. 2010-04-22.
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