◎ Sugi Atlas

Atlas / Drug / Probenecid

Probenecid

drug
On this page

Also known as BenemidBenurylHC 5006NSC-18786P-(dipropylsulfamoyl)benzoic acidProbalanProbenateProbenecid component of col-Probenecid component of colbenemidProbenecid component of orlynvahProbenecid component of probampacinProbenecid component of proben-cProbenecideProbenecidumProbampicinProbecidSID26747055SID855953SID11112135

Summary

Probenecid (CHEMBL897) is an approved small-molecule uricosuric drug (ATC M04AB01) targeting SLC22A6, SLCO1C1, and TRPV2; indicated across 17 conditions including gout and obesity disorder.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: M04AB01
  • Targets: 5 (SLC22A6, SLCO1C1, TRPV2…)
  • Indications: 17 conditions
  • Clinical trials: 58
  • Chemistry: 285.36 Da · C13H19NO4S

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL897
NameProbenecid
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID4911
ChEBICHEBI:8426
ATCM04AB01
Molecular formulaC13H19NO4S
Molecular weight285.36
InChIKeyDBABZHXKTCFAPX-UHFFFAOYSA-N

SMILES: CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O

IUPAC name: 4-(dipropylsulfamoyl)benzoic acid

ChEBI definition: A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups.

Pharmacological roles (ChEBI): uricosuric drug.

Also known as: Benemid, Benuryl, HC 5006, NSC-18786, P-(dipropylsulfamoyl)benzoic acid, Probalan, Probenate, Probenecid, Probenecid component of col-, Probenecid component of colbenemid, Probenecid component of orlynvah, Probenecid component of probampacin

Patent coverage: 48,058 distinct patent families (105,640 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
SLC22A6Organic anion transporter 1Inhibition4.90.2%Q4U2R8
SLCO1C1OATP1C1Inhibition0.1%Q9NYB5
TRPV2TRPV2Activation4.51.4%Q9Y5S1
TAS2R16TAS2R16Antagonist3.530%Q9NYV7
TAS2R38TAS2R38Antagonist3.680.1%P59533

Broader ChEMBL bioactivity targets: 20 (assay-derived). Sample: Survival motor neuron protein, Fructose-bisphosphate aldolase, Ras-related protein Rab-9A, Solute carrier family 22 member 6, Organic anion transporter 3, UDP-glucuronosyltransferase 1A7, Solute carrier family 22 member 6, Solute carrier organic anion transporter family member 1A1, Solute carrier organic anion transporter family member 1A4, Carbonic anhydrase 2.

Bioactivity

ChEMBL activities: 26 potent at pChembl ≥ 5 of 47 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
CA96.44Ki360nMCHEMBL_ACT_15003103
CA96.44Ki360nMCHEMBL_ACT_15628519
CA96.44Ki360nMCHEMBL_ACT_15681784
CA26.37Ki431nMCHEMBL_ACT_15003117
CA26.37Ki431nMCHEMBL_ACT_15628505
CA26.37Ki431nMCHEMBL_ACT_15681715
CA125.91Ki1245nMCHEMBL_ACT_15003156
CA125.91Ki1245nMCHEMBL_ACT_15628533
CA125.91Ki1245nMCHEMBL_ACT_15681802
SMN15.9Potency1259nMCHEMBL_ACT_3875314
O889095.52IC503020nMCHEMBL_ACT_15445099
SLC22A65.37Ki4300nMCHEMBL_ACT_11003109
SLC22A65.36Ki4410nMCHEMBL_ACT_11003110
SLC22A85.36Ki4410nMCHEMBL_ACT_11003111
Q9R1U75.35Ki4430nMCHEMBL_ACT_11003113
SLC22A85.31IC504930nMCHEMBL_ACT_11001485
Q9R1U75.22IC506030nMCHEMBL_ACT_11001797
SLC22A65.2IC506300nMCHEMBL_ACT_11001805
Q8VC695.2Ki6310nMCHEMBL_ACT_2182630
RAB9A5.2Potency6310nMCHEMBL_ACT_3834561
Q8VC695.19Ki6400nMCHEMBL_ACT_2182631
SLC22A65.13IC507400nMCHEMBL_ACT_11001844
Q80UJ15.08Ki8400nMCHEMBL_ACT_2202409
Q80UJ15.07Ki8511nMCHEMBL_ACT_2202408
SLC22A85.05Ki9000nMCHEMBL_ACT_10996738
SLC22A85.05IC509000nMCHEMBL_ACT_20627783

Target pathways

Aggregated over 5 target gene(s): SLC22A6, SLCO1C1, TRPV2, TAS2R16, TAS2R38.

Top Reactome pathways

17 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction2TAS2R16, TAS2R38
Signaling by GPCR2TAS2R16, TAS2R38
Transport of small molecules2SLC22A6, SLCO1C1
GPCR downstream signalling2TAS2R16, TAS2R38
G alpha (i) signalling events2TAS2R16, TAS2R38
Class C/3 (Metabotropic glutamate/pheromone receptors)2TAS2R16, TAS2R38
SLC-mediated transmembrane transport2SLC22A6, SLCO1C1
GPCR ligand binding2TAS2R16, TAS2R38
Sensory Perception2TAS2R16, TAS2R38
Sensory perception of taste2TAS2R16, TAS2R38
Sensory perception of sweet, bitter, and umami (glutamate) taste2TAS2R16, TAS2R38
TRP channels1TRPV2
R-HSA-4253661SLC22A6
Transport of vitamins, nucleosides, and related molecules1SLCO1C1
R-HSA-5491321SLC22A6
Organic anion transport by SLC22 transporters1SLC22A6
Organic anion transport by SLCO transporters1SLCO1C1

Dominant GO biological processes

GO termTargets
transmembrane transport3
sodium-independent organic anion transport2
monoatomic ion transport2
detection of chemical stimulus involved in sensory perception of bitter taste2
G protein-coupled receptor signaling pathway2
signal transduction2
sensory perception of taste2
monoatomic anion transport1
obsolete organic anion transport1
prostaglandin transport1
alpha-ketoglutarate transport1
metanephric proximal tubule development1
renal tubular secretion1
inorganic anion transport1
xenobiotic transport1

Indications & clinical

Indications

17 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
gout4MONDO:0005393EFO:0004274
obesity disorder3MONDO:0011122EFO:0001073
urinary tract infection3MONDO:0100338EFO:0003103
male infertility3MONDO:0005372EFO:0004248
cystitis3MONDO:0006032EFO:1000025
cellulitis2MONDO:0005230EFO:0003035
systolic heart failure2MONDO:0006993EFO:1001207
heart failure2MONDO:0005252EFO:0003144
neoplasm1MONDO:0005070EFO:0000616
avian influenza1MONDO:0018695EFO:0005222
brain injury1MONDO:0043510MONDO:0043510
type 2 diabetes mellitus1MONDO:0005148MONDO:0005148
alcohol abuse1MONDO:0002046MONDO:0007079
kidney disorder1MONDO:0005240EFO:0003086
diabetes mellitus1MONDO:0005015EFO:0000400
chondrocalcinosis0MONDO:0001314MONDO:0001314

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 58.

Phase distribution

PhaseTrials
PHASE126
Not specified9
PHASE36
PHASE26
PHASE45
EARLY_PHASE13
PHASE1/PHASE22
PHASE2/PHASE31

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00000894PHASE4COMPLETEDComparison of Two Drugs, Cidofovir and Ganciclovir, in Treating Patients With AIDS Who Have CMV Retinitis
NCT00304434PHASE4COMPLETEDEvaluation of Alternative Oseltamivir (Tamiflu) Dosing Strategies.
NCT00610532PHASE4TERMINATEDEvaluating the Transporter Protein Inhibitor Probenecid In Patients With Epilepsy
NCT01907373PHASE4COMPLETEDDrug Interaction Study of Olmesartan in Healthy Chinese Volunteers
NCT03965351PHASE4COMPLETEDTRPV2 Agonists in the Fontan Circulation
NCT05903859PHASE3RECRUITINGImprovement of Reproductive Function in Men With Spinal Cord Injury (SCI)
NCT01320722PHASE3COMPLETEDStudy of Vitamin D and Uric Acid Lowering on Kidney and Blood Vessel Function
NCT03354598PHASE3COMPLETEDOral Sulopenem-etzadroxil/Probenecid Versus Ciprofloxacin for Uncomplicated Urinary Tract Infection in Adult Women
NCT03357614PHASE3COMPLETEDSulopenem Followed by Sulopenem-etzadroxil/Probenecid vs Ertapenem Followed by Cipro for Complicated UTI in Adults
NCT03358576PHASE3COMPLETEDSulopenem Versus Ertapenem for Complicated Intra-abdominal Infection (cIAI)
NCT04551222PHASE2/PHASE3COMPLETEDThe Re-Prosper HF Study
NCT05584657PHASE3COMPLETEDOral Sulopenem Versus Amoxicillin/Clavulanate for Uncomplicated Urinary Tract Infection in Adult Women
NCT04939623PHASE2RECRUITINGNovel Use of Probenecid to Alleviate Symptoms of Opioid Withdrawal
NCT07118618PHASE2RECRUITINGProbenecid Administration for Alcohol Craving and Consumption
NCT07318870PHASE2NOT_YET_RECRUITINGEfficacy of Probenecid on Cluster Seizures During Anti Seizure Medication Withdrawal in Presurgical Focal Epilepsy Video-EEG Monitoring
NCT00002437PHASE2COMPLETEDThe Safety and Effectiveness of Cidofovir in the Treatment of Cytomegalovirus (CMV) of the Eyes in Patients With AIDS
NCT00288158PHASE2COMPLETEDPrimary Prevention of Hypertension in Obese Adolescents
NCT01322009PHASE1/PHASE2COMPLETEDOvercoming Membrane Transporters to Improve CNS Drug Delivery - Improving Brain Antioxidants After Traumatic Brain Injury
NCT01814319PHASE2COMPLETEDRepurposing Probenecid as a Positive Inotrope for the Treatment of Heart Failure
NCT05082909PHASE1/PHASE2COMPLETEDAddition of Probenecid to Penicillin-V Therapy
NCT07092813PHASE1RECRUITINGPharmacokinetics of Sulopenem Etzadroxil Plus Probenecid in Adolescents
NCT00000881PHASE1WITHDRAWNA Study of Cidofovir in HIV-Infected Children With Cytomegalovirus (CMV) Disease
NCT00024245PHASE1COMPLETED10-Propargyl-10-Deazaaminopterin Plus Probenecid in Treating Patients With Advanced Solid Tumors
NCT00439530PHASE1COMPLETEDPharmacologic Study of Oseltamivir in Healthy Volunteers
NCT00842400PHASE1COMPLETEDA Drug Interaction Study of VI-0521 With Metformin, Sitagliptan and Probenecid in Healthy Subjects.
NCT01021020PHASE1COMPLETEDBioequivalence Study of Colchicine Tablets
NCT01428284PHASE1COMPLETEDA Study to Assess the Effects of Multiple-Dose Probenecid on the Multiple-Dose Pharmacokinetics of Canagliflozin in Healthy Volunteers
NCT01634100PHASE1COMPLETEDDrug-interaction Trial in Healthy Subjects With Oral Administration of Empagliflozin (BI 10773), Rifampicin and Probenecid
NCT01816646PHASE1COMPLETEDIntravesical Cidofovir for Hemorrhagic Cystitis
NCT01937026PHASE1COMPLETEDA Study of Baricitinib and Probenecid in Healthy Participants
NCT03105986PHASE1COMPLETEDA Phase 1 Study to Evaluate the Effect of the Organic Anion Transporter Inhibitor Probenecid on the Pharmacokinetics of JNJ-64041575 in Healthy Adults
NCT03138759PHASE1COMPLETEDEffect of Probenecid on Pexidartinib Pharmacokinetics
NCT03296800PHASE1COMPLETEDStudy to Evaluate Effects of Probenecid, Rifampin and Verapamil on Bexagliflozin in Healthy Subjects
NCT03307252PHASE1COMPLETEDThis Study Tests the Effect of Certain Medicines on the Transport of Other Medicines in the Body of Healthy Men
NCT03466567PHASE1COMPLETEDA Trial Investigating the Effect of Probenecid and Ciclosporin on the Concentrations of SNAC in Healthy Subjects
NCT03801746PHASE1COMPLETEDDrug-Drug Interaction Study of Vadadustat With Cyclosporine, Probenecid and Rifampin
NCT03937258PHASE1COMPLETEDA Study to Assess Pharmacokinetics of PF-04965842 and Its Metabolites and Effect of Probenecid in Healthy Participants
NCT05045313PHASE1COMPLETEDA Study to Evaluate the Drug-drug Interactions (DDIs) of DBPR108 With Warfarin Sodium, Digoxin, Probenecid in Healthy Subjects
NCT05280054PHASE1UNKNOWNAV-101 Alone and in Combination With Probenecid in Healthy Subjects
NCT05497674PHASE1COMPLETEDEffects of Rifampicin and Probenecid On The Pharmacokinetic Profile Of Rongliflozin In Healthy Subjects

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of CPIC Guideline for chlorpropamide, dabrafenib, gliclazidCPICG6PD

PharmGKB also curates 0 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

65 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
ISOPROTERENOLChEMBLPhase 4 (approved)TAS2R16, TAS2R38
dinoprostonePubChemApprovedSLC22A6, SLCO1C1
MethotrexatePubChemApprovedSLC22A6, SLCO1C1
ADEFOVIR DIPIVOXILChEMBL + PubChemPhase 4 (approved)SLC22A6
AMINOHIPPURIC ACIDChEMBL + PubChemPhase 4 (approved)SLC22A6
CEFADROXILChEMBL + PubChemPhase 4 (approved)SLC22A6
CEFAZOLINChEMBL + PubChemPhase 4 (approved)SLC22A6
CEFOTAXIMEChEMBL + PubChemPhase 4 (approved)SLC22A6
CEFTRIAXONEChEMBL + PubChemPhase 4 (approved)SLC22A6
DICLOFENACChEMBL + PubChemPhase 4 (approved)SLC22A6
DIFLUNISALChEMBL + PubChemPhase 4 (approved)SLC22A6
ETODOLACChEMBL + PubChemPhase 4 (approved)SLC22A6
FLURBIPROFENChEMBL + PubChemPhase 4 (approved)SLC22A6
INDOMETHACINChEMBL + PubChemPhase 4 (approved)SLC22A6
KETOPROFENChEMBL + PubChemPhase 4 (approved)SLC22A6
NAPROXENChEMBL + PubChemPhase 4 (approved)SLC22A6
PIROXICAMChEMBL + PubChemPhase 4 (approved)SLC22A6
BENZBROMARONEChEMBLPhase 4 (approved)SLC22A6
CEFAMANDOLEChEMBLPhase 4 (approved)SLC22A6
CEFOPERAZONEChEMBLPhase 4 (approved)SLC22A6
CEPHALORIDINEChEMBLPhase 4 (approved)SLC22A6
CEPHALOTHINChEMBLPhase 4 (approved)SLC22A6
CIDOFOVIRChEMBLPhase 4 (approved)SLC22A6
IBUPROFENChEMBLPhase 4 (approved)SLC22A6
PROPYLTHIOURACILChEMBLPhase 4 (approved)TAS2R38
ADEFOVIRChEMBL + PubChemPhase 3 (approved)SLC22A6
CANNABINOLChEMBLPhase 3TRPV2
PAMIPARIBChEMBLPhase 3SLC22A6
ROLOFYLLINEChEMBLPhase 3SLC22A6
BETAMIPRONChEMBLPhase 2SLC22A6
CANNABIDIVARINChEMBLPhase 2TRPV2
CANNABIGEROLChEMBLPhase 2TRPV2
ELLAGIC ACIDChEMBLPhase 2SLC22A6
OCTANOIC ACIDChEMBLPhase 2SLC22A6
TETRAHYDROCANNABIVARINChEMBLPhase 2TRPV2
VERINURADChEMBLPhase 2SLC22A6
ZONAMPANELChEMBLPhase 2SLC22A6
AcyclovirPubChemApprovedSLC22A6
AspirinPubChemApprovedSLC22A6
BumetanidePubChemApprovedSLC22A6
CannabidiolPubChemApprovedTRPV2
caprylic acidPubChemApprovedSLC22A6
CaspofunginPubChemApprovedSLC22A6
CimetidinePubChemApprovedSLC22A6
CiprofloxacinPubChemApprovedSLC22A6
DigoxinPubChemApprovedSLCO1C1
DinoprostPubChemApprovedSLC22A6
ErtugliflozinPubChemApprovedSLC22A6
FluoresceinPubChemApprovedSLC22A6
FurosemidePubChemApprovedSLC22A6
GanciclovirPubChemApprovedSLC22A6
HydrochlorothiazidePubChemApprovedSLC22A6
LamivudinePubChemApprovedSLC22A6
LinagliptinPubChemApprovedSLC22A6
LiothyroninePubChemApprovedSLCO1C1
LosartanPubChemApprovedSLC22A6
oseltamivir acidPubChemApprovedSLC22A6
PenciclovirPubChemApprovedSLC22A6
Penicillin GPubChemApprovedSLC22A6
PhenylbutazonePubChemApprovedSLC22A6

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot