Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H17NO3 |
Molecular Weight | 223.2683 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCOC1=CC=C(CC(=O)NO)C=C1
InChI
InChIKey=MXJWRABVEGLYDG-UHFFFAOYSA-N
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)
DescriptionCurator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/referrals/Bufexamac/human_referral_000209.jsp&mid=WC0b01ac05805c516f | https://www.ncbi.nlm.nih.gov/pubmed/14607020 | https://www.ncbi.nlm.nih.gov/pubmed/25751058 | https://www.ncbi.nlm.nih.gov/pubmed/21258344 | https://www.ncbi.nlm.nih.gov/pubmed/27126280
Curator's Comment: Description was created based on several sources, including http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/referrals/Bufexamac/human_referral_000209.jsp&mid=WC0b01ac05805c516f | https://www.ncbi.nlm.nih.gov/pubmed/14607020 | https://www.ncbi.nlm.nih.gov/pubmed/25751058 | https://www.ncbi.nlm.nih.gov/pubmed/21258344 | https://www.ncbi.nlm.nih.gov/pubmed/27126280
Bufexamac is a nonsteroidal antiinflammatory drug (NSAID) used in topical formulations to treat dermatological diseases (eczema and dermatitis) and proctological conditions (haemorrhoids and anal fissure). Bufexamac-containing medicines have been available in EU Member States since the 1970s. In 2010 European Medicines Agency recommends revocation of marketing authorisations for bufexamac due to high risk of contact allergies. The phenolic bufexamac decomposition products could be the reason for its eczema-provoking properties frequently described in the literature. Bufexamac is a class IIb histone deacetylase (HDAC6, HDAC10) inhibitor. Bufexamac also triggered an HDAC6-independent, hypoxia-like response by stabilizing Hypoxia-inducible factor 1-alpha, providing a possible mechanistic explanation of its adverse, pro-inflammatory effects. Bufexamac was capable of specifically inhibiting leukotriene A4 hydrolase and attenuating lung inflammation in acute lung injury mouse model.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14607020 |
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Target ID: CHEMBL1865 |
10.7 µM [Kd] | ||
Target ID: CHEMBL5103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21258344 |
12.3 µM [Kd] | ||
Target ID: CHEMBL4261 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25751058 |
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Target ID: CHEMBL4618 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27126280 |
15.86 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | BUFEXAMAC Approved UseBufexamac 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. |
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Primary | BUFEXAMAC Approved UseBufexamac 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. |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Skin sensitizing properties of arylalcanoic acids and their analogues. | 1979 Sep |
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Effects of intra-articular injections of bufexamac suspension in healthy horses. | 2001 Oct |
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Allergic contact dermatitis with spreading over extensive regions due to topical use of 5% bufexamac ointment. | 2004 Feb |
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Frequency of contact allergy in German children and adolescents patch tested between 1995 and 2002: results from the Information Network of Departments of Dermatology and the German Contact Dermatitis Research Group. | 2004 Sep |
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Screening for new antioxidative compounds for topical administration using skin lipid model systems. | 2005 Sep 15 |
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Allergic contact dermatitis to topical drugs--epidemiological risk assessment. | 2008 Aug |
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[Facial allergic contact dermatitis. Data from the IVDK and review of literature]. | 2009 Jan |
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[Bufexamac-induced pigmented purpuric eruption]. | 2009 May |
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Contact dermatitis due to topical drugs. | 2009 Oct |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21258344
Treatment of peripheral blood mononuclear cells with bufexamac inhibits the secretion of IFN-α (EC50 = 8.9 uM)
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QM02AA09
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M02AA09
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M01AB17
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QM01AB17
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m2749
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C166783
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DB13346
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Bufexamac
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SUB05961MIG
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DTXSID7045368
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CHEMBL94394
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ACTIVE MOIETY