Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00557)
Name
Probenecid
Synonyms    Click to Show/Hide the Synonyms of This API
probenecid; 57-66-9; 4-(Dipropylsulfamoyl)benzoic acid; Probenecid acid; Benemid; Probecid; Benecid; Probenemid; Benuryl; Probalan; Probexin; Prolongine; Tubophan; Uricosid; Apurina; Proben; Synergid R; p-(Dipropylsulfamoyl)benzoic acid; 4-[(dipropylamino)sulfonyl]benzoic acid; Probenecida; Probenecide; Probenecidum; 4-((Dipropylamino)sulfonyl)benzoic acid; 4-(Di-n-propylsulfamoyl)benzoesaeure; 4-(N,N-Dipropylsulfamoyl)benzoesaeure; Benzoic acid, 4-[(dipropylamino)sulfonyl]-; NCI-C56097; Benzoic acid, p-(dipropylsulfamoyl)-; 4-(N,N-Dipropylsulfamoyl)benzoic Acid; p-(Dipropylsulfamyl)benzoic acid; MFCD00038402; NSC 18786; CHEBI:8426; Probenecid (Benemid); UNII-PO572Z7917; Benzoic acid, 4-((dipropylamino)sulfonyl)-; CHEMBL897; MLS000028496; 4-Dipropylsulfamoyl-benzoic acid; Benemide; Probenid; Robenecid; Polycillin-BRB; NSC-18786; PO572Z7917; CAS-57-66-9; probenicid; NCGC00016251-08; SMR000058280; DSSTox_CID_1188; DSSTox_RID_75998; DSSTox_GSID_21188; Probenecide [INN-French]; Probenecidum [INN-Latin]; Probenecida [INN-Spanish]; Benemid (TN); CCRIS 3643; HSDB 3387; SR-01000003108; EINECS 200-344-3; BRN 2815775; AI3-50078; Probenecid [USP:INN:BAN:JAN]; Prestwick_809; Spectrum_000834; ColBenemid (Salt/Mix); Opera_ID_677; Prestwick0_000542; Prestwick1_000542; Prestwick2_000542; Prestwick3_000542; Spectrum2_001294; Spectrum3_000554; Spectrum4_000486; Spectrum5_001419; Benemid; Benecid; Benuryl; Epitope ID:180853; SCHEMBL3663; Polycillin-PRB (Salt/Mix); BIDD:PXR0092; Oprea1_416955; WLN: QVR DSWN3&3; BSPBio_000583; BSPBio_002227; KBioGR_000971; KBioSS_001314; MLS001076472; BIDD:GT0626; DivK1c_000056; SPECTRUM1500502; SPBio_001327; SPBio_002504; BPBio1_000643; GTPL4357; Probenecid (JP17/USP/INN); ZINC1982; DTXSID9021188; HMS500C18; KBio1_000056; KBio2_001314; KBio2_003882; KBio2_006450; KBio3_001727; AOB5799; NINDS_000056; HMS1569N05; HMS1920J22; HMS2092C03; HMS2096N05; HMS2233N05; HMS3259G04; HMS3369L18; HMS3652O17; HMS3713N05; HMS3743E07; HMS3885I18; p-(Dipropylsulfamoyl) benzoic acid; Pharmakon1600-01500502; ALBB-025846; BCP21785; HY-B0545; NSC18786; STR06053; Tox21_110328; Tox21_202110; Tox21_302928; BDBM50206509; CCG-39232; KM0133; NSC757292; SBB028597; STL229614; 4-Dipropylsulfamoyl-benzoic acid anion; AKOS000165123; Tox21_110328_1; 4-(Di-n-propylsulfamoyl)benzoic acid; AC-2023; DB01032; HC 5006; MCULE-8664946016; NC00530; NSC-757292; SB17360; IDI1_000056; 4-(Di-n-propylaminosulfonyl)benzoic acid; NCGC00016251-01; NCGC00016251-02; NCGC00016251-03; NCGC00016251-04; NCGC00016251-05; NCGC00016251-06; NCGC00016251-07; NCGC00016251-09; NCGC00016251-10; NCGC00016251-13; NCGC00023829-03; NCGC00023829-04; NCGC00023829-05; NCGC00023829-06; NCGC00023829-07; NCGC00256441-01; NCGC00259659-01; ST099094; 4-(N,N-dipropylaminosulphonyl)benzoic acid; SBI-0051492.P003; 4-Dipropylsulfamoyl-benzoic acid(probenecid); AB00052080; SW196943-3; EN300-69677; C07372; D00475; J10155; AB00052080_15; AB00052080_16; 038P402; Q900898; Q-201621; SR-01000003108-2; SR-01000003108-3; BRD-K95237249-001-05-9; BRD-K95237249-001-15-8; Z53037954; Probenecid, European Pharmacopoeia (EP) Reference Standard; Probenecid, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Hyperuricaemia ICD-11: 5C55 [1]
PubChem CID
4911
Formula
C13H19NO4S
Canonical SMILES
CCCN(CCC)S(=O)(=O)C1=CC=C(C=C1)C(=O)O
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=4911"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 285.36 Topological Polar Surface Area 83.1
XlogP 3.2 Complexity 374
Heavy Atom Count 19 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Full List of Drug Formulations (DFMs) Containing This API
          Probenecid 500 mg tablet Click to Show/Hide the Full List of Formulation(s):          7 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Polyvinyl alcohol; Silicon dioxide; Aluminum oxide; Cellulose, microcrystalline; Polyethylene glycols; Povidone k29/32; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; Marlex Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols; Povidones; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Polysorbate 80; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Westminster Pharmaceuticals, LLC
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Polysorbate 80; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycol; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company Watson Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 1; Fd&c yellow no. 6; Magnesium stearate; Titanium dioxide; Polysorbate 80; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols; Sodium starch glycolate type a potato
                   Dosage Form Oral Tablet
                   Company HHS/Program Support Center/Supply Service Center; Physicians Total Care
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 1 DIG Info Solute carrier SLCO2B1 (Ki = 13 uM) [2]
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polysorbate 80 DIG Info Prostaglandin G/H synthase 1 (IC50 = 1 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 6 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Sodium carbonate; Titanium dioxide; Triacetin; Silicon dioxide; Cellulose, microcrystalline; Hypromelloses; Polydextrose; Polyethylene glycols; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Aphena Pharma Solutions-Tennessee; Carilion Materials Management; Mylan Pharamceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 7 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Sodium lauryl sulfate; D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Talc; Titanium dioxide; Silicon dioxide; Aluminum oxide; Cellulose, microcrystalline; Polyethylene glycols; Polyvinyl alcohol, unspecified; Povidone, unspecified; Sodium starch glycolate type a potato; Starch, corn
                   Dosage Form Oral Tablet
                   Company Lannett Company
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
Sodium lauryl sulfate DIG Info Solute carrier SLCO2B1 (Ki = 1.98 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
References
1 FDA label for approved probenecid from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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