Probenecid (CED0002789)

Record Information
Version1.0
Creation Date2016-05-22 03:30:21 UTC
Update Date2026-08-19 01:53:31 UTC
Accession NumberCHEM016398
Identification
Common NameProbenecid
ClassSmall Molecule
Description
Probenecid (C13H19NO4S) is a compound with an average molecular weight of 285.36 g/mol. Probenecid belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It is utilized as a treatment for hyperuricemia (PMC10346988). The compound is found in or released from 45 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antigout preparations and gynecologicals. It is also recorded in building and construction materials such as floors and ceilings, household items including coins, and food, food processing, and cookware categories including food preservation, processing meats, processing fish, preparation of wort, and fermentation processes for beer. Additionally, it is found in household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, other smoking requisites, non electric simulated smoking devices, and cigar cigarettes. It is further linked to electrical and electronic equipment, including antennas, amplifiers, communication cables or conductors, colour television systems, auxiliary devices, and 23 other sources. The recorded exposure route for probenecid is oral. The compound interacts with five recorded protein targets, acting as an antagonist, inhibitor, or inhibitory allosteric modulator of pannexin-1 (PANX1), organic anion transporter 3 (SLC22A8), solute carrier family 22 member 6 (SLC22A6), solute carrier family 22 member 11 (SLC22A11), and one other protein.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
4-((Dipropylamino)sulfonyl)benzoic acidChEBI
4-(Di-N-propylsulfamoyl)benzoesaeureChEBI
4-(N,N-Dipropylsulfamoyl)benzoesaeureChEBI
p-(Dipropylsulfamoyl)benzoic acidChEBI
Probenecid acidChEBI
ProbenecidaChEBI
ProbenecideChEBI
ProbenecidumChEBI
BenemidKegg
4-((Dipropylamino)sulfonyl)benzoateGenerator
4-((Dipropylamino)sulphonyl)benzoateGenerator
4-((Dipropylamino)sulphonyl)benzoic acidGenerator
4-(Di-N-propylsulphamoyl)benzoesaeureGenerator
4-(N,N-Dipropylsulphamoyl)benzoesaeureGenerator
p-(Dipropylsulfamoyl)benzoateGenerator
p-(Dipropylsulphamoyl)benzoateGenerator
p-(Dipropylsulphamoyl)benzoic acidGenerator
ProbenicidHMDB
Biokanol brand OF probenecidHMDB
Ophthalmic brand OF probenecidHMDB
Probenecid martec brandHMDB
Merck brand OF probenecidHMDB
Probenecid major brandHMDB
Probenecid parmed brandHMDB
Probenecid weimerHMDB
Zenith brand OF probenecidHMDB
BenecidHMDB
BenurylHMDB
ICN brand OF probenecidHMDB
IDIS brand OF probenecidHMDB
Martec brand OF probenecidHMDB
Pro-cidHMDB
ProbecidHMDB
Probenecid zenith brandHMDB
Major brand OF probenecidHMDB
Parmed brand OF probenecidHMDB
Valdecasas brand OF probenecidHMDB
Chemical FormulaC13H19NO4S
Average Molecular Mass285.359 g/mol
Monoisotopic Mass285.103 g/mol
CAS Registry Number57-66-9
IUPAC Name4-(dipropylsulfamoyl)benzoic acid
Traditional Nameprobenecid
SMILESCCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(O)=O
InChI IdentifierInChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)
InChI KeyDBABZHXKTCFAPX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzenesulfonyl group
  • Benzoyl
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organosulfur compound
  • 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 Solubility0.42 g/LALOGPS
logP1.52ALOGPS
logP2.44ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.68 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity73.81 m³·mol⁻¹ChemAxon
Polarizability29.96 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-005c-9430000000-66fa2eec09e65b520fd4Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9322000000-86b32ee67219d76aee32Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f76-0190000000-ce053a8c64308bc3ebbbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f76-0190000000-f6f2df3671a359ea4574Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f76-0190000000-f6f2df3671a359ea4574Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f76-0190000000-ce053a8c64308bc3ebbbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fen-3950100000-c43ebdb497f6a0e8c974Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9000000000-5663daf3af027bcf4bd5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9000000000-3280579def3da504b6e3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9000000000-f7e60026073ba954d843Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dm-3920000000-d373c6be2068a852f878Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000y-1980000000-e8ccc1214006fa858e38Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9500000000-62dfa7da11ed364a0fe9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9100000000-40231ffb30b72d29e268Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ko-2090000000-e9339c027711ad986a00Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9270000000-89113f1adccbbe5ce2c6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-c76de17d7d7e7fff001cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0090000000-fcc637b2f7443930eaa9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-0390000000-d84958808d58246de403Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03kc-4900000000-81cfffb64fe9ae84692aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000x-0090000000-7babe007c72f09d68c2eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1190000000-7f80163c40b7f72b3e08Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-9000000000-b04d355dbd4b8be3a462Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0090000000-b62a8dd0c7fbd3f45a69Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kh3-9450000000-b314f1bcfa44850dacf4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9520000000-e8ccc0bfff93660781c8Not 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
1878.0Log mg/kg[1100:3300]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hyperuricemiais_treatment_forNot AvailablePMC10346988
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
366Antigout preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
534Still Video CamerasElectrical & Electronic EquipmentNot Available
535Superconducting Magnets And Superconducting CoilsElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
551Processing FishFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
571CoinsHousehold itemsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot 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
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureOrganic anion transporter 3O88909Mus musculusPredicted (SEA)0.0778492
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)12.1445
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)10.2761
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)10.2761
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)9.41976
Click to view 3D structureOrganic anion transporter 3Q9R1U7Rattus norvegicusPredicted (SEA)0.0778492
UDP-3-O-acyl-N-acetylglucosamine deacetylase structureClick to view 3D structureUDP-3-O-acyl-N-acetylglucosamine deacetylaseO67648Aquifex aeolicus (strain VF5)Predicted (SEA)4.9045
Click to view 3D structureSolute carrier family 22 member 20Q80UJ1Mus musculusPredicted (SEA)0.0778492
Taste receptor type 2 member 14 structureClick to view 3D structureTaste receptor type 2 member 14Q9NYV8HumansPredicted (SEA)0.934191
Collagenase 3 structureClick to view 3D structureCollagenase 3P45452HumansPredicted (SEA)64.7706
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)120.199
Matrix metalloproteinase-9 structureClick to view 3D structureMatrix metalloproteinase-9P14780HumansPredicted (SEA)108.833
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)1.47914
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)87.8139
Neutrophil collagenase structureClick to view 3D structureNeutrophil collagenaseP22894HumansPredicted (SEA)89.7602
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)72.5555
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)52.2368
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)38.8468
Matrix metalloproteinase-14 structureClick to view 3D structureMatrix metalloproteinase-14P50281HumansPredicted (SEA)112.804
Click to view 3D structureSolute carrier family 22 member 6Q8VC69Mus musculusPredicted (SEA)0.0778492
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)50.602
Stromelysin-1 structureClick to view 3D structureStromelysin-1P08254HumansPredicted (SEA)121.133
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)2.80257
Matrix metalloproteinase-16 structureClick to view 3D structureMatrix metalloproteinase-16P51512HumansPredicted (SEA)19.4623
Macrophage metalloelastase structureClick to view 3D structureMacrophage metalloelastaseP39900HumansPredicted (SEA)107.588
Concentrations
Not Available
External Links
DrugBank IDDB01032
HMDB IDHMDB0015166
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProbenecid
Chemspider ID4742
ChEBI ID8426
PubChem Compound ID4911
Kegg Compound IDC07372
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Butler D: Wartime tactic doubles power of scarce bird-flu drug. Nature. 2005 Nov 3;438(7064):6.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21861129
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21938493
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22321288
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22561103
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22582566
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22681402
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22854641
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23129053
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=509935