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 It was withdrawn in Europe and Australia [1] because of allergic reactions.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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<span class="mw-page-title-main">Dermatitis</span> Inflammation of the skin

Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can vary from small to covering the entire body. Dermatitis is often called eczema, and the difference between those terms is not standardized.

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<span class="mw-page-title-main">Diclofenac</span> Nonsteroidal anti-inflammatory drug


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<span class="mw-page-title-main">Mefenamic acid</span> Chemical compound

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<span class="mw-page-title-main">Moisturizer</span> Type of cosmetics

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Atopic dermatitis (AD), also known as atopic eczema, is a long-term type of inflammation of the skin (dermatitis). It results in itchy, red, swollen, and cracked skin. Clear fluid may come from the affected areas, which often thickens over time. While the condition may occur at any age, it typically starts in childhood, with changing severity over the years. In children under one year of age, much of the body may be affected. As children get older, the areas on the insides of the knees and elbows are most commonly affected. In adults, the hands and feet are most commonly affected. Scratching the affected areas worsens the symptoms, and those affected have an increased risk of skin infections. Many people with atopic dermatitis develop hay fever or asthma.

<span class="mw-page-title-main">Betamethasone dipropionate</span> Glucocorticoid steroid (chemical compound)

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<span class="mw-page-title-main">Moxifloxacin</span> Antibiotic

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Mometasone, also known as mometasone y 3 s, is a steroid medication used to treat certain skin conditions, hay fever, and asthma. Specifically it is used to prevent rather than treat asthma attacks. It can be applied to the skin, inhaled, or used in the nose. Mometasone furoate, not mometasone, is used in medical products.

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<span class="mw-page-title-main">Bromfenac</span> Chemical compound

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) marketed in the US as an ophthalmic solution by ISTA Pharmaceuticals for short-term, local use. Prolensa and Bromday are the once-daily formulation of bromfenac, while Xibrom was approved for twice-daily administration. In the European Union, the brand name is Yellox. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery.

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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): 255–65. 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.