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probenecid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| 2268 | 57-66-9 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
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.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 1 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| 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 µM/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 |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | -0.397 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 0.597 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 47.973 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 2.692 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 12.060 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 18.780 | % | High | 1 |
| herg | hERG pIC50 | 4.547 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 3.381 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 3.327 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 9.700 | % | High | 1 |
| kinase-safety-class | ACVR2A,ACVR2B,ACVRL1,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK4,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,GRK3,GSK3B,IKBKB,ITK,JAK1,JAK2,MAP2K6,MAP3K21,MAP3K7,MAPK12,MAPK7,MAPK9,MAPKAPK2,MTOR,NTRK2,PDK1,PDK2,PDPK1,PIK3CB,PIK3CD,PIK3CG,PIM2,PLK1,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1,ZAP70 | 54 | |||
| kinase-selectivity-class | AXL,GRK2,MAPK7,PDK4,TEK | 5 | |||
| mdck-mdr1-bcrp-efflux | MDCK-MDR1-BCRP efflux ratio | 1.247 | High | 1 | |
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 1.309 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 16.406 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 20.040 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 1.127 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 12.860 | % | High | 1 |
| rat-kpuu-brain | Rat brain Kpuu | 0.164 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 16.069 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 83.240 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 9.980 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 984.011 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| April 26, 1951 | FDA |
FDA Adverse Event Reporting System (Female)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Adenovirus infection | 65.95 | 41.18 | 13 | 582 | 4609 | 90623243 |
| Aplastic anaemia | 52.30 | 41.18 | 13 | 582 | 13256 | 90614596 |
FDA Adverse Event Reporting System (Male)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Adenovirus infection | 102.15 | 23.02 | 26 | 1173 | 6783 | 42613353 |
| Lip haemorrhage | 32.25 | 23.02 | 7 | 1192 | 913 | 42619223 |
| Platelet transfusion | 23.08 | 23.02 | 6 | 1193 | 1688 | 42618448 |
FDA Adverse Event Reporting System (Geriatric)
| MedDRA adverse event term | Likelihood ratio | Likelihood ratio threshold | Patients taking drug having adverse event | Patients taking drug not having adverse event | Patients not taking drug having adverse event | Patients not taking drug not having adverse event |
|---|---|---|---|---|---|---|
| Adenovirus infection | 173.49 | 24.38 | 39 | 1676 | 10955 | 110576629 |
| Aplastic anaemia | 59.92 | 24.38 | 20 | 1695 | 24288 | 110563296 |
| Cystitis haemorrhagic | 38.02 | 24.38 | 12 | 1703 | 12197 | 110575387 |
| Pancreatitis acute | 36.26 | 24.38 | 18 | 1697 | 60256 | 110527328 |
| Lip haemorrhage | 33.21 | 24.38 | 7 | 1708 | 1445 | 110586139 |
| Drug ineffective for unapproved indication | 27.30 | 24.38 | 18 | 1697 | 102820 | 110484764 |
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | J01DI55 | ANTIINFECTIVES FOR SYSTEMIC USE ANTIBACTERIALS FOR SYSTEMIC USE OTHER BETA-LACTAM ANTIBACTERIALS Other cephalosporins and penems |
| ATC | M04AB01 | MUSCULO-SKELETAL SYSTEM ANTIGOUT PREPARATIONS ANTIGOUT PREPARATIONS Preparations increasing uric acid excretion |
| ATC | M04AC51 | MUSCULO-SKELETAL SYSTEM ANTIGOUT PREPARATIONS ANTIGOUT PREPARATIONS Preparations with no effect on uric acid metabolism |
| MeSH PA | D000277 | Adjuvants, Pharmaceutic |
| MeSH PA | D006074 | Gout Suppressants |
| MeSH PA | D010592 | Pharmaceutic Aids |
| MeSH PA | D014528 | Uricosuric Agents |
| MeSH PA | D018501 | Antirheumatic Agents |
| CHEBI has role | CHEBI:22587 | antiviral agent |
| CHEBI has role | CHEBI:33282 | antibacterial agent |
| CHEBI has role | CHEBI:35441 | antiinfective agent |
| CHEBI has role | CHEBI:35526 | hypoglycemic agent |
| CHEBI has role | CHEBI:35554 | cardiovascular drug |
| CHEBI has role | CHEBI:35610 | antineoplastic agent |
| CHEBI has role | CHEBI:35841 | uricosuric drug |
| CHEBI has role | CHEBI:35845 | gout suppressant |
| CHEBI has role | CHEBI:63726 | neuroprotective agent |
| CHEBI has role | CHEBI:74518 | anti-obesity agent |
| CHEBI has role | CHEBI:231911 | renoprotective agent |
Related Drugs by ATC class:
J01DI Other cephalosporins and penems 5 drugs
M04AB Preparations increasing uric acid excretion 5 drugs
M04AC Preparations with no effect on uric acid metabolism 2 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| 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 |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 3.46 | acidic |
Orange Book patent data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Patent number | Patent expiration date | Patent use |
|---|---|---|---|---|---|---|---|---|---|---|
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | 7795243 | June 3, 2029 | USE IN TREATING UNCOMPLICATED URINARY TRACT INFECTIONS CAUSED BY ESCHERICHIA COLI, KLEBSIELLA PNEUMONIAE, OR PROTEUS MIRABILIS |
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | 11554112 | April 1, 2039 | USE IN TREATING UNCOMPLICATED URINARY TRACT INFECTIONS CAUSED BY ESCHERICHIA COLI, KLEBSIELLA PNEUMONIAE, OR PROTEUS MIRABILIS |
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | 12109197 | April 1, 2039 | USE IN TREATING UNCOMPLICATED URINARY TRACT INFECTIONS CAUSED BY ESCHERICHIA COLI, KLEBSIELLA PNEUMONIAE, OR PROTEUS MIRABILIS |
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | 11478428 | Dec. 23, 2039 | USE IN TREATING UNCOMPLICATED URINARY TRACT INFECTIONS CAUSED BY ESCHERICHIA COLI, KLEBSIELLA PNEUMONIAE, OR PROTEUS MIRABILIS |
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | 12544337 | Dec. 23, 2039 | USE IN TREATING UNCOMPLICATED URINARY TRACT INFECTIONS CAUSED BY ESCHERICHIA COLI, KLEBSIELLA PNEUMONIAE, OR PROTEUS MIRABILIS |
Orange Book exclusivity data (new drug applications)
| Formulation strength | Trade name | Applicant | Application number | Approval date | Type | Dose form | Route | Exclusivity date | Description |
|---|---|---|---|---|---|---|---|---|---|
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | Oct. 25, 2029 | NEW CHEMICAL ENTITY |
| 500MG;500MG | ORLYNVAH | ITERUM THERAP | N213972 | Oct. 25, 2024 | RX | TABLET | ORAL | Oct. 25, 2034 | GENERATING ANTIBIOTIC INCENTIVES NOW |
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Solute carrier family 22 member 11 | Transporter | INHIBITOR | IC50 | 4.26 | CHEMBL | CHEMBL | |||
| Solute carrier family 22 member 6 | Transporter | INHIBITOR | IC50 | 4.90 | IUPHAR | CHEMBL | |||
| Solute carrier family 22 member 8 | Transporter | INHIBITOR | IC50 | 5.05 | CHEMBL | CHEMBL | |||
| Solute carrier family 22 member 12 | Transporter | IC50 | 4.30 | CHEMBL | |||||
| UDP-glucuronosyltransferase 1-7 | Enzyme | Ki | 4.02 | CHEMBL | |||||
| Carbonic anhydrase 2 | Enzyme | Ki | 6.37 | CHEMBL | |||||
| Carbonic anhydrase 9 | Enzyme | Ki | 6.44 | CHEMBL | |||||
| Carbonic anhydrase 12 | Enzyme | Ki | 5.90 | CHEMBL | |||||
| Solute carrier family 22 member 6 | Transporter | Ki | 5.20 | CHEMBL | |||||
| Solute carrier family 22 member 20 | Transporter | Ki | 5.08 | CHEMBL | |||||
| Transient receptor potential cation channel subfamily V member 2 | Ion channel | ACTIVATOR | EC50 | 4.50 | IUPHAR |
External reference:
| ID | Source |
|---|---|
| 4017872 | VUID |
| N0000146225 | NUI |
| D00475 | KEGG_DRUG |
| 4017872 | VANDF |
| C0033209 | UMLSCUI |
| CHEBI:8426 | CHEBI |
| RTO | PDB_CHEM_ID |
| CHEMBL897 | ChEMBL_ID |
| DB01032 | DRUGBANK_ID |
| D011339 | MESH_DESCRIPTOR_UI |
| 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 |
| PO572Z7917 | INXIGHT DRUGS |
Pharmaceutical products:
| Product | Category | Ingredients | NDC | Form | Quantity | Route | Marketing | Label |
|---|---|---|---|---|---|---|---|---|
| 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 | 16571-831 | TABLET | 500 mg | ORAL | ANDA | 12 sections |
| Probenecid and Colchicine | Human Prescription Drug Label | 2 | 16571-832 | TABLET | 500 mg | ORAL | ANDA | 12 sections |
| Probenecid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 43353-839 | TABLET, FILM COATED | 500 mg | ORAL | ANDA | 14 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 | 68151-1993 | TABLET, FILM COATED | 500 mg | ORAL | ANDA | 13 sections |
| Probenecid and Colchicine | HUMAN PRESCRIPTION DRUG LABEL | 2 | 70518-4644 | TABLET | 500 mg | ORAL | ANDA | 12 sections |
| Probenecid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 70518-4649 | TABLET | 500 mg | ORAL | ANDA | 12 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 |
| Probenecid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 72162-2237 | TABLET, FILM COATED | 500 mg | ORAL | ANDA | 13 sections |
| Probenecid | HUMAN PRESCRIPTION DRUG LABEL | 1 | 72162-2386 | TABLET | 500 mg | ORAL | ANDA | 12 sections |
| ORLYNVAH | HUMAN PRESCRIPTION DRUG LABEL | 2 | 81153-100 | TABLET, FILM COATED | 500 mg | ORAL | NDA | 31 sections |