Details of the Drug

General Information of Drug (ID: DMMFWOJ)

Drug Name

Probenecid

Synonyms

Apurina; Bencid; Benecid; Benemid; Benemide; Benuryl; Panuric; Parabenem; Probalan; Probampacin; Probecid; Proben; Probenecida; Probenecide; Probenecidum; Probenemid; Probenicid; Probenid; Probexin; Prolongine; Robenecid; Sulprin; Tubophan; Uricosid; Urocid; Biokanol Brand of Probenecid; ICN Brand of Probenecid; IDIS Brand of Probenecid; Major Brand of Probenecid; Martec Brand of Probenecid; Merck Brand of Probenecid; Ophthalmic Brand of Probenecid; Parmed Brand of Probenecid; Probenecid Major Brand; Probenecid Martec Brand; Probenecid Parmed Brand; Probenecid Weimer; Probenecid Zenith Brand; Probenecid acid; Synergid R; Valdecasas Brand of Probenecid; Zenith Brand of Probenecid; Benemid (TN); Benuryl (TN); Col-BENEMID; ColBenemid (co mponent of); ColBenemid (component of); P-[Dipropylsulfamoyl]benzoic acid; Polycillin-BRB; Pro-Cid; Probenecida [INN-Spanish]; Probenecide [INN-French]; Probenecidum [INN-Latin]; P-(Dipropylsulfamoyl)benzoic acid; P-(Dipropylsulfamyl)benzoic acid; Polycillin-PRB (component of); Probenecid [INN:BAN:JAN]; Probenecid (JP15/USP/INN); 4-((Dipropylamino)sulfonyl)benzoic acid;4-(Di-n-propylsulfamoyl)benzoesaeure; 4-(Dipropylsulfamoyl)benzoic acid; 4-(N,N-Dipropylsulfamoyl)benzoesaeure; 4-[(dipropylamino)sulfonyl]benzoic acid

Indication

Disease Entry	ICD 11	Status	REF
Acute gonococcal cervicitis	N.A.	Approved	[1]
Gout	FA25	Approved	[2]
Hyperuricaemia	5C55.Y	Approved	[2]
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Therapeutic Class

Uricosuric Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

285.36

Logarithm of the Partition Coefficient (xlogp)

3.2

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Bioavailability: 99% of drug becomes completely available to its intended biological destination(s) [4]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.25 mL/min/kg [5]
Elimination: 1.2% of drug is excreted from urine in the unchanged form [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 6 - 12 hours [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 58.52161 micromolar/kg/day [6]
Unbound Fraction: The unbound fraction of drug in plasma is 0.13% [5]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.13 L/kg [5]

Chemical Identifiers

Formula: C13H19NO4S
IUPAC Name: 4-(dipropylsulfamoyl)benzoic acid
Canonical SMILES: CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O
InChI: InChI=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)
InChIKey: DBABZHXKTCFAPX-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4911
ChEBI ID: CHEBI:8426
CAS Number: 57-66-9
DrugBank ID: DB01032
TTD ID: D0L7FM
VARIDT ID: DR00232
INTEDE ID: DR1341
ACDINA ID: D00557

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Solute carrier family 22 member 8 (SLC22A8)	TTTQR47	S22A8_HUMAN	Blocker	[7]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Monocarboxylate transporter 6 (SLC16A5)	DT3I124	MOT6_HUMAN	Substrate	[8]
Multidrug resistance-associated protein 2 (ABCC2)	DTFI42L	MRP2_HUMAN	Substrate	[9]
Organic anion transporting polypeptide 1A2 (SLCO1A2)	DTE2B1D	SO1A2_HUMAN	Substrate	[10]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)_{Main DME}	DEYGVN4	UD11_HUMAN	Substrate	[11]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-binding cassette sub-family C member 2 (ABCC2)	OTJSIGV5	MRP2_HUMAN	Gene/Protein Processing	[12]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[13]
Cytochrome P450 3A4 (CYP3A4)	OTQGYY83	CP3A4_HUMAN	Gene/Protein Processing	[14]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[13]
Multidrug resistance-associated protein 1 (ABCC1)	OTGUN89S	MRP1_HUMAN	Gene/Protein Processing	[15]
Organic anion transporter 3 (SLC22A8)	OT8BY933	S22A8_HUMAN	Gene/Protein Processing	[16]
Organic anion transporter 7 (SLC22A9)	OTO4BJCC	S22A9_HUMAN	Gene/Protein Processing	[17]
Sodium-coupled monocarboxylate transporter 1 (SLC5A8)	OTA0WELF	SC5A8_HUMAN	Gene/Protein Processing	[18]
Solute carrier family 22 member 11 (SLC22A11)	OTAJLNJZ	S22AB_HUMAN	Gene/Protein Processing	[19]
Solute carrier family 22 member 12 (SLC22A12)	OT72ZAWS	S22AC_HUMAN	Gene/Protein Processing	[20]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Probenecid (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Cefuroxime	DMSIMD8	Moderate	Decreased elimination of Probenecid caused by Cefuroxime mediated competitive inhibition of renal tubular secretion.	Acute bronchitis [CA42]	[21]
Glipizide	DMZA5PQ	Moderate	Increased risk of hypoglycemia by the combination of Probenecid and Glipizide.	Acute diabete complication [5A2Y]	[22]
Cefamandole	DMNEXZF	Moderate	Decreased elimination of Probenecid caused by Cefamandole mediated competitive inhibition of renal tubular secretion.	Anaerobic bacterial infection [1A00-1A09]	[21]
Cefotetan	DM07TX3	Moderate	Decreased elimination of Probenecid caused by Cefotetan mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Ceftizoxime	DM3VOGS	Moderate	Decreased elimination of Probenecid caused by Ceftizoxime mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Ticarcillin	DM4ME02	Minor	Decreased elimination of Probenecid caused by Ticarcillin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[23]
Cefoperazone	DM53PV8	Moderate	Decreased elimination of Probenecid caused by Cefoperazone mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Cefprozil	DM7DSYP	Moderate	Decreased elimination of Probenecid caused by Cefprozil mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Cefepime	DMHVWIK	Moderate	Decreased elimination of Probenecid caused by Cefepime mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Imipenem	DMI9FBP	Minor	Decreased elimination of Probenecid caused by Imipenem mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[24]
Meticillin	DMIKHN0	Minor	Decreased elimination of Probenecid caused by Meticillin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[23]
Cefpodoxime	DMJUNY5	Moderate	Decreased elimination of Probenecid caused by Cefpodoxime mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Cefadroxil	DMMC345	Moderate	Decreased elimination of Probenecid caused by Cefadroxil mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Bacampicillin	DMP54C7	Minor	Decreased elimination of Probenecid caused by Bacampicillin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[23]
Cefazolin	DMPDYFR	Moderate	Decreased elimination of Probenecid caused by Cefazolin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Cefonicid	DMTX2BH	Moderate	Decreased elimination of Probenecid caused by Cefonicid mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Cefradine	DMUNSWV	Moderate	Decreased elimination of Probenecid caused by Cefradine mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[25]
Cloxacillin	DMUTL7O	Minor	Decreased elimination of Probenecid caused by Cloxacillin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[23]
Amoxicillin	DMUYNEI	Minor	Decreased elimination of Probenecid caused by Amoxicillin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[23]
Cefoxitin	DMY8NC4	Moderate	Decreased elimination of Probenecid caused by Cefoxitin mediated competitive inhibition of renal tubular secretion.	Bacterial infection [1A00-1C4Z]	[21]
Pexidartinib	DMS2J0Z	Major	Decreased metabolism of Probenecid caused by Pexidartinib mediated inhibition of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[26]
Ceftibuten	DMWV2AG	Moderate	Decreased elimination of Probenecid caused by Ceftibuten mediated competitive inhibition of renal tubular secretion.	Bronchitis [CA20]	[21]
Ardeparin	DMYRX8B	Minor	Increased risk of bleeding by the combination of Probenecid and Ardeparin.	Coronary thrombosis [BA43]	[27]
Benzylpenicillin	DMS9503	Minor	Decreased elimination of Probenecid caused by Benzylpenicillin mediated competitive inhibition of renal tubular secretion.	Discovery agent [N.A.]	[23]
Clonazepam	DMTO13J	Minor	Decreased metabolism of Probenecid caused by Clonazepam.	Epilepsy/seizure [8A61-8A6Z]	[28]
ITI-007	DMUQ1DO	Moderate	Decreased metabolism of Probenecid caused by ITI-007 mediated inhibition of UGT.	Insomnia [7A00-7A0Z]	[29]
Quazepam	DMY4D87	Minor	Decreased metabolism of Probenecid caused by Quazepam.	Insomnia [7A00-7A0Z]	[28]
Estazolam	DMZGXUM	Minor	Decreased metabolism of Probenecid caused by Estazolam.	Insomnia [7A00-7A0Z]	[28]
Remimazolam	DMLVSYX	Minor	Decreased metabolism of Probenecid caused by Remimazolam.	Labour/delivery anaesthesia complication [JB0C]	[28]
Glycerol phenylbutyrate	DMDGRQO	Major	Decreased renal excretion of Probenecid caused by Glycerol phenylbutyrate.	Liver disease [DB90-DB9Z]	[30]
Phenylbutyrate	DMBHPDW	Major	Decreased renal excretion of Probenecid caused by Phenylbutyrate.	Metabolism inborn error [5C50]	[31]
Choline salicylate	DM8P137	Moderate	Antagonize the effect of Probenecid when combined with Choline salicylate.	Postoperative inflammation [1A00-CA43]	[32]
Selexipag	DMAHSU0	Moderate	Decreased metabolism of Probenecid caused by Selexipag mediated inhibition of UGT.	Pulmonary hypertension [BB01]	[33]
Salsalate	DM13P4C	Moderate	Antagonize the effect of Probenecid when combined with Salsalate.	Rheumatoid arthritis [FA20]	[32]
Cephapirin	DMV2JNY	Moderate	Decreased elimination of Probenecid caused by Cephapirin mediated competitive inhibition of renal tubular secretion.	Sepsis [1G40-1G41]	[25]
Deferiprone	DMS2M7O	Moderate	Decreased metabolism of Probenecid caused by Deferiprone mediated inhibition of UGT.	Thalassaemia [3A50]	[34]
Tolbutamide	DM02AWV	Moderate	Increased risk of hypoglycemia by the combination of Probenecid and Tolbutamide.	Type 2 diabetes mellitus [5A11]	[22]
Doripenem	DM9UCJK	Moderate	Decreased elimination of Probenecid caused by Doripenem mediated competitive inhibition of renal tubular secretion.	Urinary tract infection [GC08]	[24]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF	E00255	17730	Colorant
Carbonic acid disodium salt	E00199	10340	Alkalizing agent; Buffering agent; Diluent; Dispersing agent
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol	E00666	Not Available	Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Triacetin	E00080	5541	Humectant; Plasticizing agent; Solvent
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⏷ Show the Full List of 13 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Probenecid 500 mg tablet	500 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Probenecid FDA Label
2	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4357).
3	BDDCS applied to over 900 drugs
4	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	Transport of organic anions across the basolateral membrane of proximal tubule cells. Rev Physiol Biochem Pharmacol. 2003;146:95-158.
8	Quercetin, Morin, Luteolin, and Phloretin Are Dietary Flavonoid Inhibitors of Monocarboxylate Transporter 6. Mol Pharm. 2017 Sep 5;14(9):2930-2936.
9	MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Int J Cancer. 2005 Sep 20;116(5):824-9.
10	Characterization of the efflux transport of 17beta-estradiol-D-17beta-glucuronide from the brain across the blood-brain barrier. J Pharmacol Exp Ther. 2001 Jul;298(1):316-22.
11	Modulation of 3'-azido-3'-deoxythymidine catabolism by probenecid and acetaminophen in freshly isolated rat hepatocytes. Biochem Pharmacol. 1991 Sep 12;42(7):1475-80.
12	MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. Int J Cancer. 2005 Sep 20;116(5):824-9. doi: 10.1002/ijc.21013.
13	Evaluation and mechanistic analysis of the cytotoxicity of the acyl glucuronide of nonsteroidal anti-inflammatory drugs. Drug Metab Dispos. 2014 Jan;42(1):1-8. doi: 10.1124/dmd.113.054478. Epub 2013 Oct 8.
14	Use of immortalized human hepatocytes to predict the magnitude of clinical drug-drug interactions caused by CYP3A4 induction. Drug Metab Dispos. 2006 Oct;34(10):1742-8.
15	Mercury induces multidrug resistance-associated protein gene through p38 mitogen-activated protein kinase. Toxicol Lett. 2005 Jan 15;155(1):143-50. doi: 10.1016/j.toxlet.2004.09.007.
16	Targeting organic anion transporter 3 with probenecid as a novel anti-influenza a virus strategy. Antimicrob Agents Chemother. 2013 Jan;57(1):475-83. doi: 10.1128/AAC.01532-12. Epub 2012 Nov 5.
17	Inhibition of organic anion transporter (OAT) activity by cigarette smoke condensate. Toxicol In Vitro. 2017 Oct;44:27-35.
18	The human tumour suppressor gene SLC5A8 expresses a Na+-monocarboxylate cotransporter. J Physiol. 2004 Jun 15;557(Pt 3):719-31. doi: 10.1113/jphysiol.2004.063859. Epub 2004 Apr 16.
19	Neonicotinoid pesticides poorly interact with human drug transporters. J Biochem Mol Toxicol. 2019 Oct;33(10):e22379. doi: 10.1002/jbt.22379. Epub 2019 Jul 31.
20	Clinical and molecular analysis of patients with renal hypouricemia in Japan-influence of URAT1 gene on urinary urate excretion. J Am Soc Nephrol. 2004 Jan;15(1):164-73. doi: 10.1097/01.asn.0000105320.04395.d0.
21	Brown G, Zemcov SJ, Clarke AM "Effect of probenecid on cefazolin serum concentrations." J Antimicrob Chemother 31 (1993): 1009-11. [PMID: 8360120]
22	Abad S, Moachon L, Blanche P, Bavoux F, Sicard D, Salmon-Ceron D "Possible interaction between glicazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia." Br J Clin Pharmacol 52 (2001): 456-7. [PMID: 11678792]
23	Allen MB, Fitzpatrick RW, Barratt A, Cole RB "The use of probenecid to increase the serum amoxycillin levels in patients with bronchiectasis." Respir Med 84 (1990): 143-6. [PMID: 2371437]
24	Product Information. Doribax (doripenem). Ortho McNeil Pharmaceutical, Raritan, NJ.
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26	Product Information. Turalio (pexidartinib). Daiichi Sankyo, Inc., Parsippany, NJ.
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29	Product Information. Caplyta (lumateperone). Intra-Cellular Therapies, Inc., New York, NY.
30	Product Information. Buphenyl (sodium phenylbutyrate). Horizon Pharma USA Inc, Northbrook, IL.
31	Goldbart A, Press J, Sofer S, Kapelushnik J "Near fatal acute colchicine intoxication in a child. A case report." Eur J Pediatr 159 (2000): 895-7. [PMID: 11131346]
32	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
33	Cerner Multum, Inc. "Australian Product Information.".
34	Product Information. Ferriprox (deferiprone). ApoPharma USA Inc, Rockville, MD.