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	In general: Over-the-counter (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;
CompTox Dashboard (EPA)	DTXSID7045368 ;
ECHA InfoCard	100.017.683
Chemical and physical data
Formula	C12H17NO3
Molar mass	223.272 g·mol−1
3D model (JSmol)	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 It was withdrawn in Europe and Australia^[1] because of allergic reactions.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]} 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]

References

^ "Bufexamac Safety advisory - risk of serious skin reactions". Therapeutic Goods Administration (TGA). 2020.
^ 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.
^ 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.
^ 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.
^ "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" (PDF). European Medicines Agency. 2010-04-22. Archived from the original (PDF) on 2010-05-31. Retrieved 2010-05-01.

[1] "Bufexamac Safety advisory - risk of serious skin reactions". Therapeutic Goods Administration (TGA). 2020.

[Arzneistoff-Profile-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 from the original (PDF) on 2010-05-31. Retrieved 2010-05-01.

[1]

[2]

[3]

[4]

[5]

[6]

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen^† Carprofen^‡ Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen^# Ibuproxam Indoprofen^† Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin^‡ Tiaprofenic acid Vedaprofen^‡ Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
category commons portal

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Topical, rectal
ATC code	M01AB17 (WHO) M02AA09 (WHO)
Legal status
Legal status	In general: Over-the-counter (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
CompTox Dashboard (EPA)	DTXSID7045368
ECHA InfoCard	100.017.683
Chemical and physical data
Formula	C₁₂H₁₇NO₃
Molar mass	223.272 g·mol⁻¹
3D model (JSmol)	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