probenecid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
2268 57-66-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • probenecid
  • benecid
  • probecid
  • probenecid acid
The 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.
  • Molecular weight: 285.36
  • Formula: C13H19NO4S
  • CLOGP: 3.37
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 74.68
  • ALOGS: -2.83
  • ROTB: 6

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1.20 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 58.52 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.13 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 0.25 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.13 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 26, 1951 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Adenovirus infection 41.33 28.70 9 551 2821 46682681
Multiple organ dysfunction syndrome 36.84 28.70 16 544 51694 46633808

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Adenovirus infection 62.63 22 17 1104 4251 29947106
Neuromyopathy 35.21 22 8 1113 964 29950393
Myopathy 22.72 22 10 1111 10576 29940781

Pharmacologic Action:

SourceCodeDescription
ATC M04AB01 MUSCULO-SKELETAL SYSTEM
ANTIGOUT PREPARATIONS
ANTIGOUT PREPARATIONS
Preparations increasing uric acid excretion
MeSH PA D000277 Adjuvants, Pharmaceutic
MeSH PA D018501 Antirheumatic Agents
MeSH PA D006074 Gout Suppressants
MeSH PA D010592 Pharmaceutic Aids
MeSH PA D014528 Uricosuric Agents
CHEBI has role CHEBI:35841 uricosuric agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hyperuricemia indication 35885006 DOID:1920
Articular gout indication 48440001 DOID:13189
Chronic gouty arthritis indication 68451005
Adjunct Treatment to Inhibit Renal Drug Excretion indication
Peptic ulcer contraindication 13200003 DOID:750
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Diarrhea contraindication 62315008
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Anemia due to enzyme deficiency contraindication 111577008
Disorder of muscle contraindication 129565002 DOID:423
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Impaired renal function disorder contraindication 197663003
Rhabdomyolysis contraindication 240131006
Renal dialysis contraindication 265764009
Infectious mononucleosis contraindication 271558008 DOID:8568
Uric acid renal calculus contraindication 274401005
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Aplastic anemia contraindication 306058006 DOID:12449
Bone marrow depression contraindication 307762000
Pseudomembranous enterocolitis contraindication 397683000
Granulocytopenic disorder contraindication 417672002
Vomiting contraindication 422400008
Uric Acid Nephropathy Gout contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.46 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Solute carrier family 22 member 6 Transporter INHIBITOR IC50 4.90 IUPHAR CHEMBL
Solute carrier family 22 member 11 Transporter INHIBITOR DRUGBANK CHEMBL
Solute carrier family 22 member 8 Transporter INHIBITOR WOMBAT-PK CHEMBL
Carbonic anhydrase 12 Enzyme Ki 5.90 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 6.44 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 6.37 CHEMBL
Solute carrier family 22 member 12 Transporter IC50 4.30 CHEMBL
UDP-glucuronosyltransferase 1-7 Enzyme Ki 4.02 CHEMBL
Solute carrier family 22 member 20 Transporter Ki 5.08 CHEMBL
Solute carrier family 22 member 6 Transporter Ki 5.20 CHEMBL
Transient receptor potential cation channel subfamily V member 2 Unclassified ACTIVATOR EC50 4.50 IUPHAR

External reference:

IDSource
4017872 VUID
N0000146225 NUI
D00475 KEGG_DRUG
4017872 VANDF
C1564151 UMLSCUI
CHEBI:8426 CHEBI
CHEMBL897 ChEMBL_ID
D011339 MESH_DESCRIPTOR_UI
DB01032 DRUGBANK_ID
4911 PUBCHEM_CID
4357 IUPHAR_LIGAND_ID
563 INN_ID
PO572Z7917 UNII
8698 RXNORM
128 MMSL
5356 MMSL
d00031 MMSL
002321 NDDF
387365004 SNOMEDCT_US
66094001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 0527-1367 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Probenecid and Colchicine HUMAN PRESCRIPTION DRUG LABEL 2 0591-5325 TABLET 500 mg ORAL ANDA 13 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 0591-5347 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 10135-541 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 11819-282 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 43353-839 TABLET, FILM COATED 500 mg ORAL ANDA 14 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 43353-991 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Probenecid and Colchicine Human Prescription Drug Label 2 50742-263 TABLET 500 mg ORAL ANDA 13 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 54868-0159 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 63629-8213 TABLET, FILM COATED 500 mg ORAL ANDA 12 sections
Probenecid and Colchicine Human Prescription Drug Label 2 64980-149 TABLET 500 mg ORAL ANDA 13 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 68151-1993 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 69367-154 TABLET 500 mg ORAL ANDA 13 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 71335-1697 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections
Probenecid HUMAN PRESCRIPTION DRUG LABEL 1 71626-999 TABLET, FILM COATED 500 mg ORAL ANDA 13 sections