Bufexamac (CED0014736)

Record Information
Version1.0
Creation Date2016-05-22 05:07:24 UTC
Update Date2026-08-18 19:26:10 UTC
Accession NumberCHEM018274
Identification
Common NameBufexamac
ClassSmall Molecule
Description
Bufexamac is an organic compound with the chemical formula C12H17NO3 and an average molecular weight of 223.27 g/mol. Bufexamac belongs to the phenylacetamides, a subclass of benzene and substituted derivatives within the organic compounds. This compound is associated with 11 recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is found in antiinflammatory and antirheumatic products as well as topical products for joint and muscular pain. It is also released from household cleaning and consumer products, specifically non electric simulated smoking devices. Additionally, it is found in electrical and electronic equipment, including amplifiers, discharge lamps, electric switches, electrodes, and electrically stimulated smoking devices, among three other sources. The recorded route of exposure for this substance is topical. At a molecular level, bufexamac interacts with four recorded protein targets. It acts as an inhibitor of Prostaglandin G/H synthase 1 (PTGS1) and Prostaglandin G/H synthase 2 (PTGS2). Furthermore, it targets the proteins Protein deacetylase HDAC6 and Polyamine deacetylase HDAC10.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-(p-Butoxyphenyl)-acetohydroxamic acidChEBI
4-Butoxy-N-hydroxybenzeneacetamideChEBI
4-Butoxyphenylacetohydroxamic acidChEBI
Acide p-butoxyphenylacethydroxamiqueChEBI
BufexamacoChEBI
BufexamacumChEBI
Bufexamic acidChEBI
p-Butoxyphenylacetohydroxamic acidChEBI
AndermKegg
2-(p-Butoxyphenyl)-acetohydroxamateGenerator
4-ButoxyphenylacetohydroxamateGenerator
BufexamateGenerator
p-ButoxyphenylacetohydroxamateGenerator
AllergipuranMeSH
Bioglan brand OF bufexamacMeSH
Bufexamac scheurich brandMeSH
Sanofi synthelabo brand OF bufexamacMeSH
Whitehall brand OF bufexamacMeSH
WindolMeSH
AHP brand OF bufexamacMeSH
Bufexamac-ratiopharmMeSH
DroxarylMeSH
MalipuranMeSH
Scheurich brand OF bufexamacMeSH
P Butoxyphenylacethydroxamic acidMeSH
Merck dura brand OF bufexamacMeSH
Bufexamac dermapharm brandMeSH
Bufexamac galenpharma brandMeSH
Bufexamac ratiopharmMeSH
Pfizer brand OF bufexamacMeSH
BufexamacMeSH
BufalMeSH
BufedermMeSH
Bufexamac ratiopharm brandMeSH
Dermapharm brand OF bufexamacMeSH
JomaxMeSH
ParadermMeSH
P-Butoxyphenylacethydroxamic acidMeSH
Bufexamac ahp brandMeSH
Bufexamac pfizer brandMeSH
Pierre fabre brand OF bufexamacMeSH
Bufexamac bioglan brandMeSH
Bufexamac whitehall brandMeSH
BufexamacratiopharmMeSH
GALENpharma brand OF bufexamacMeSH
ParfenacMeSH
DuradermalMeSH
Ratiopharm brand OF bufexamacMeSH
Chemical FormulaC12H17NO3
Average Molecular Mass223.272 g/mol
Monoisotopic Mass223.121 g/mol
CAS Registry Number2438-72-4
IUPAC NameN-hydroxy2-(4-butoxyphenyl)ethanimidic acid
Traditional Namejomax
SMILESCCCCOC1=CC=C(CC(O)=NO)C=C1
InChI IdentifierInChI=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)
InChI KeyMXJWRABVEGLYDG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Hydroxamic acid
  • Carboxylic acid derivative
  • Ether
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.5ALOGPS
logP2.79ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.54ChemAxon
pKa (Strongest Basic)0.39ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.05 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity61.81 m³·mol⁻¹ChemAxon
Polarizability24.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrumsplash10-08mi-0920000000-e2854ce6292c5d0a1c8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-4910100000-7ff98d442e9aa0a2f64dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1090000000-f24ae0d85b1376dd6695Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-5390000000-1064111002b4036cfbbbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-7900000000-789660a43653a49880b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-5900000000-91ae318ee7bf4a0c8ebbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-4900000000-15c66804db050221c331Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3900000000-a41498b64629a3eda39cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0920000000-9e2d982e08339f818cf6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-0900000000-435c1f72113403e534faNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-9de68224c670d85b5621Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-496edd1f1dfb18e3bc93Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-3e269c82012ba53557c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-80c7b8b429b26dfbbfc6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08mi-0920000000-e2854ce6292c5d0a1c8cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-4910100000-7ff98d442e9aa0a2f64dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-3790000000-4039782277746e9f762fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-3910000000-1551e839edb87240079dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9300000000-0b2e57d6765bd1d7de8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2790000000-a888ce6056e5f170d8f7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0cdm-7920000000-844caa547238084d9a5dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052b-7900000000-dd69ba5273b008ba5b9fNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2565.0Log mg/kg[1400:4600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
233BrushesPersonal care & cosmeticsNot Available
363Antiinflammatory and antirheumatic productsHealthcare, pharmaceuticals & veterinary productsNot Available
364Topical products for joint and muscular painHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)1.79053
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)72.5555
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)79.4841
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)18.2946
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)256.591
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)231.601
Click to view 3D structureTransient receptor potential cation channel subfamily V member 3Q8K424Mus musculusPredicted (SEA)14.3243
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)564.407
Click to view 3D structureNeuronal acetylcholine receptor subunit alpha-7P22770Gallus gallusPredicted (SEA)1.86838
Click to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP12527Rattus norvegicusPredicted (SEA)37.679
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)260.406
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)253.399
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)229.733
Click to view 3D structureSarcoplasmic/endoplasmic reticulum calcium ATPase 3Q64518Mus musculusPredicted (SEA)12.6116
Click to view 3D structureCytosolic phospholipase A2 betaP0C869HumansPredicted (SEA)4.43741
Histamine H3 receptor structureClick to view 3D structureHistamine H3 receptorQ9Y5N1HumansPredicted (SEA)217.978
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)98.4014
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)195.791
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)612.051
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)521.979
Muscarinic acetylcholine receptor M2 structureClick to view 3D structureMuscarinic acetylcholine receptor M2P08172HumansPredicted (SEA)213.229
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)100.581
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)418.984
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)211.906
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)79.2505
Concentrations
Not Available
External Links
DrugBank IDDB13346
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBufexamac
Chemspider IDNot Available
ChEBI ID31317
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12635026
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=140084
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14607020
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18353041
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19093092
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21392031
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21429689
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21950459
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=22828265
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=22881467
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2529420
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2958428
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=3388925
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=350491
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=3555968
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=509935
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=7750277
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=9165205