Probenecid (CHEM016398)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:30:21 UTC
Update Date2016-11-09 01:15:23 UTC
Accession NumberCHEM016398
Identification
Common NameProbenecid
ClassSmall Molecule
DescriptionThe prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-005c-9430000000-66fa2eec09e65b520fd4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9322000000-86b32ee67219d76aee32Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0f76-0190000000-ce053a8c64308bc3ebbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0f76-0190000000-f6f2df3671a359ea4574Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f76-0190000000-f6f2df3671a359ea4574Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f76-0190000000-ce053a8c64308bc3ebbbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0fen-3950100000-c43ebdb497f6a0e8c974Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-03di-9000000000-5663daf3af027bcf4bd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-03di-9000000000-3280579def3da504b6e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-03di-9000000000-f7e60026073ba954d843Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03dm-3920000000-d373c6be2068a852f878Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-000y-1980000000-e8ccc1214006fa858e38Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-03di-9500000000-62dfa7da11ed364a0fe9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-03di-9100000000-40231ffb30b72d29e268Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ko-2090000000-e9339c027711ad986a00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9270000000-89113f1adccbbe5ce2c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c76de17d7d7e7fff001cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-fcc637b2f7443930eaa9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-0390000000-d84958808d58246de403Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03kc-4900000000-81cfffb64fe9ae84692aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0090000000-7babe007c72f09d68c2eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1190000000-7f80163c40b7f72b3e08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9000000000-b04d355dbd4b8be3a462Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-b62a8dd0c7fbd3f45a69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kh3-9450000000-b314f1bcfa44850dacf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9520000000-e8ccc0bfff93660781c8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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