Identification
- Summary
Bufexamac is an NSAID used to treat skin conditions like atopic eczema and inflammatory dermatoses.
- Generic Name
- Bufexamac
- DrugBank Accession Number
- DB13346
- Background
Bufexamac is a non-steroidal anti-inflammatory drug (NSAID) under the market name Droxaryl, Malipuran, Paraderm and Parfenac. It is typically administered topically for the treatment of subacute and chronic eczema of the skin, including atopic eczema and other inflammatory dermatoses, as well as sunburn and other minor burns, and itching. It has also been used in suppositories in combination with local anaesthetics indicated for haemorrhoids. The use of bufexamac has been discontinued in Canada and the United States, which may be due to undetermined clinical efficacy and a high prevalence of contact sensitization 2. Bufexamac was also withdrawn by the EMA in April 2010.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Bufexamac (DB13346)
- Weight
- Average: 223.272
Monoisotopic: 223.120843411 - Chemical Formula
- C12H17NO3
- Synonyms
- 2-(p-Butoxyphenyl)-acetohydroxamic acid
- 4-Butoxy-N-hydroxybenzeneacetamide
- 4-Butoxyphenylacetohydroxamic acid
- Acide p-butoxyphenylacethydroxamique
- Bufexamac
- bufexamaco
- bufexamacum
- Bufexamic acid
- p-Butoxyphenylacetohydroxamic acid
- External IDs
- CP 1044 J3
- CP-1044-J3
Pharmacology
- Indication
Indicated for the treatment of various skin conditions, such as atopic eczema and other inflammatory dermatoses.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Anal fissures Combination Product in combination with: Bismuth subgallate (DB13909), Titanium dioxide (DB09536), Lidocaine (DB00281) •••••••••••• Used in combination for symptomatic treatment of Hemorrhoids Combination Product in combination with: Titanium dioxide (DB09536), Bismuth subgallate (DB13909), Lidocaine (DB00281) •••••••••••• Used in combination for symptomatic treatment of Pruritus ani Combination Product in combination with: Titanium dioxide (DB09536), Lidocaine (DB00281), Bismuth subgallate (DB13909) •••••••••••• - Contraindications & Blackbox Warnings
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Bufexamac is a topically-active anti-inflammatory agent that inhibits the cyclooxygenase enzyme. In cutaneous and deep experimental inflammation, topical administration of bufexamac exerted a dose-related anti-inflammatory effect 1. In guinea pigs, bufexamax was shown to be more active than topical acetylsalicylic acid 5% or phenylbutazone 5% in delaying the local increase in temperature resulting from UV exposure 1. Bufexamac is unlikely to have any effect on wound healing 1.
- Mechanism of action
The full mechanism of action is unclear. It is proposed that bufexamac acts similarly to other non-steroidal anti-inflammatory drugs to inhibit prostaglandin biosynthesis in vitro, via inhibiting cyclo-oxygenase (COX) enzymes 1. Systematically administered bufexamac may accumulate preferentially in the adrenal cortex of rats and may play a role in adrenal stimulation; however its topical anti-inflammatory action is likely to be independent of this effect 1.
Target Actions Organism AProstaglandin G/H synthase 1 inhibitorHumans AProstaglandin G/H synthase 2 inhibitorHumans UHistone deacetylase 6 inhibitorHumans UHistone deacetylase 10 inhibitorHumans - Absorption
Method of application affects the extent of cutaneous absorption 1. Following rectal administration as suppositories, the systemic absorption was reported to be low 3.
- Volume of distribution
No data available.
- Protein binding
No data available.
- Metabolism
No data available.
- Route of elimination
Following topical administration of 5% bufexamac, the recovery in the urine was 3.5% of the applied dose within 144 hours 1. Studies in healthy volunteers receiving an oral dose of 125 to 500 mg indicate that an average of 80% of the total dose is excreted in the urine within 48 hours 1.
- Half-life
No data available.
- Clearance
No data available.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The LD50 in rat following oral and intraperitoneal administration is 3370 mg/kg and 805 mg/kg, respectively MSDS. Subcutaneous LD50 in mouse is >5000 mg/kg MSDS. Mild skin irritation was seen in rabbits following dermal application of 750 mg/30d(l) MSDS. Non-steroidal anti-inflammatory drug (NSAID) overdose may produce nausea, vomiting, indigestion and upper abdominal pain. Other effects may include drowsiness, dizziness, confusion, disorientation, lethargy MSDS.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The risk or severity of adverse effects can be increased when Aceclofenac is combined with Bufexamac. Acemetacin The risk or severity of adverse effects can be increased when Bufexamac is combined with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Acetylsalicylic acid can be decreased when used in combination with Bufexamac. Alclofenac The risk or severity of adverse effects can be increased when Alclofenac is combined with Bufexamac. Aminophenazone The risk or severity of adverse effects can be increased when Aminophenazone is combined with Bufexamac. - Food Interactions
- No interactions found.
Products
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Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Norfemac Cream - 5% Cream 5 % Topical Hoechst Marion Roussel 1995-12-31 1999-08-11 Canada 
Norfemac Ointment - 5% Ointment 5 % Topical Hoechst Marion Roussel 1995-12-31 1999-08-11 Canada
Categories
- ATC Codes
- M01AB17 — Bufexamac
- M01AB — Acetic acid derivatives and related substances
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Acetamides
- Acetic Acid Derivatives and Related Substances
- Agents causing hyperkalemia
- Amides
- Amines
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antineoplastic Agents
- Antirheumatic Agents
- Benzene Derivatives
- Benzeneacetamides
- Histone Deacetylase Inhibitors
- Hydroxamic Acids
- Hydroxy Acids
- Hydroxylamines
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- Peripheral Nervous System Agents
- Sensory System Agents
- Topical Products for Joint and Muscular Pain
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylacetamides
- Direct Parent
- Phenylacetamides
- Alternative Parents
- Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Hydroxamic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alkyl aryl ether / Aromatic homomonocyclic compound / Carbonyl group / Carboxylic acid derivative / Ether / Hydrocarbon derivative / Hydroxamic acid / Organic nitrogen compound / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aromatic ether, hydroxamic acid (CHEBI:31317)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4T3C38J78L
- CAS number
- 2438-72-4
- InChI Key
- MXJWRABVEGLYDG-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 2-(4-butoxyphenyl)-N-hydroxyacetamide
- SMILES
- CCCCOC1=CC=C(CC(=O)NO)C=C1
References
- General References
- Brogden RN, Pinder RM, Sawyer PR, Speight TM, Avery GS: Bufexamac: a review of its pharmacological properties and therapeutic efficacy in inflammatory dermatoses. Drugs. 1975;10(5-6):351-6. [Article]
- Kranke B, Szolar-Platzer C, Komericki P, Derhaschnig J, Aberer W: Epidemiological significance of bufexamac as a frequent and relevant contact sensitizer. Contact Dermatitis. 1997 Apr;36(4):212-5. [Article]
- Glowania HJ, Hampl B: [Results of a study of the resorption of bufexamac following rectal administration]. Z Hautkr. 1988 Mar 21;63(3):211. [Article]
- FDA Thailand: Mastu-S (bufexamac/bismuth subgallate/titanium dioxide/lidocaine hydrochloride) for rectal administration [Link]
- External Links
- PDB Entries
- 5bpp
- MSDS
- Download (352 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Cream Topical Cream Topical 5 % Ointment Topical 5 % - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 153 to 155 MSDS water solubility Immiscible MSDS - Predicted Properties
Property Value Source Water Solubility 0.233 mg/mL ALOGPS logP 2.09 ALOGPS logP 1.97 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 8.86 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.56 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 61.29 m3·mol-1 Chemaxon Polarizability 24.58 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.3271532 predictedDarkChem Lite v0.1.0 [M-H]- 149.36546 predictedDeepCCS 1.0 (2019) [M+H]+ 164.2007532 predictedDarkChem Lite v0.1.0 [M+H]+ 151.72346 predictedDeepCCS 1.0 (2019) [M+Na]+ 160.24022 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Brogden RN, Pinder RM, Sawyer PR, Speight TM, Avery GS: Bufexamac: a review of its pharmacological properties and therapeutic efficacy in inflammatory dermatoses. Drugs. 1975;10(5-6):351-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Prostaglandin-endoperoxide synthase activity
- Specific Function
- Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Brogden RN, Pinder RM, Sawyer PR, Speight TM, Avery GS: Bufexamac: a review of its pharmacological properties and therapeutic efficacy in inflammatory dermatoses. Drugs. 1975;10(5-6):351-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
- Gene Name
- HDAC6
- Uniprot ID
- Q9UBN7
- Uniprot Name
- Histone deacetylase 6
- Molecular Weight
- 131418.19 Da
References
- Bantscheff M, Hopf C, Savitski MM, Dittmann A, Grandi P, Michon AM, Schlegl J, Abraham Y, Becher I, Bergamini G, Boesche M, Delling M, Dumpelfeld B, Eberhard D, Huthmacher C, Mathieson T, Poeckel D, Reader V, Strunk K, Sweetman G, Kruse U, Neubauer G, Ramsden NG, Drewes G: Chemoproteomics profiling of HDAC inhibitors reveals selective targeting of HDAC complexes. Nat Biotechnol. 2011 Mar;29(3):255-65. doi: 10.1038/nbt.1759. Epub 2011 Jan 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events. Histone deacetylases act via the formation of large multiprotein complexes.
- Specific Function
- Enzyme binding
- Gene Name
- HDAC10
- Uniprot ID
- Q969S8
- Uniprot Name
- Histone deacetylase 10
- Molecular Weight
- 71444.08 Da
References
- Bantscheff M, Hopf C, Savitski MM, Dittmann A, Grandi P, Michon AM, Schlegl J, Abraham Y, Becher I, Bergamini G, Boesche M, Delling M, Dumpelfeld B, Eberhard D, Huthmacher C, Mathieson T, Poeckel D, Reader V, Strunk K, Sweetman G, Kruse U, Neubauer G, Ramsden NG, Drewes G: Chemoproteomics profiling of HDAC inhibitors reveals selective targeting of HDAC complexes. Nat Biotechnol. 2011 Mar;29(3):255-65. doi: 10.1038/nbt.1759. Epub 2011 Jan 23. [Article]
Drug created at June 23, 2017 20:40 / Updated at May 29, 2021 18:11