Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1341)
Drug Name
Probenecid
Synonyms
Probalan; Probampacin; Probecid; Proben; Probenecid acid; Probenecida; Probenecide; Probenecidum; Probenemid; Probenid; Probexin; Prolongine; Robenecid; Synergid R; Tubophan; Uricosid; p-(Dipropylsulfamoyl)benzoic acid; probenecid; probenicid; Apurina; Benecid; Benemid; Benemide; Benuryl; Polycillin-BRB; Polycillin-PRB; 4-((Dipropylamino)sulfonyl)benzoic acid; 4-(Di-n-propylsulfamoyl)benzoesaeure; 4-(Dipropylsulfamoyl)benzoic acid; 4-[(dipropylamino)sulfonyl]benzoic acid; 57-66-9; Benzoic acid, 4-[(dipropylamino)sulfonyl]-
Indication Hyperuricaemia [ICD11: 5C55] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 285.36 Topological Polar Surface Area 83.1
Heavy Atom Count 19 Rotatable Bond Count 7
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4911
PubChem SID
9576 ; 81789 ; 855953 ; 3162120 ; 5227618 ; 7847541 ; 7980385 ; 8149496 ; 8153022 ; 10321755 ; 10528000 ; 11112135 ; 11335231 ; 11360470 ; 11363728 ; 11366290 ; 11368852 ; 11371827 ; 11374110 ; 11377014 ; 11461442 ; 11466570 ; 11467690 ; 11485063 ; 11486240 ; 11489110 ; 11490370 ; 11492301 ; 11494648 ; 14873183 ; 17389752 ; 24898976 ; 26611889 ; 26680013 ; 26747055 ; 26747056 ; 26751571 ; 29223989 ; 46506554 ; 47588826 ; 47662104 ; 47885248 ; 47959564 ; 47959565 ; 48034940 ; 48110289 ; 48334309 ; 48414371 ; 48416470 ; 48423998
ChEBI ID
CHEBI:8426
CAS Number
57-66-9
TTD Drug ID
D0L7FM
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2-hydroxy Probenecid DM002969
71356202
Oxidation - Hydroxylation 1 [3] , [4]
Mono-N-DepropylProbenecid DM002970
611818
Oxidation - Deethylation 1 [3] , [4]
Probenecid acyl glucuronide DM002968
53447407
Conjugation - Glucuronidation 1 [2] , [4]
Probenecid metabolite M1 DM002971
71356201
Oxidation - Hydroxylation 1 [3] , [4]
Probenecid metabolite M2 DM002972 N. A. Oxidation - Oxidation 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002151 Probenecid Probenecid acyl glucuronide Conjugation - Glucuronidation UGT1A1 [2], [4]
MR002152 Probenecid 2-hydroxy Probenecid Oxidation - Hydroxylation Unclear [3], [4]
MR002153 Probenecid Mono-N-DepropylProbenecid Oxidation - Deethylation Unclear [3], [4]
MR002154 Probenecid Probenecid metabolite M1 Oxidation - Hydroxylation Unclear [3], [4]
MR002155 Probenecid Probenecid metabolite M2 Oxidation - Oxidation Unclear [3], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
References
1 Probenecid was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Clinical pharmacokinetics of probenecid Clin Pharmacokinet. 1981 Mar-Apr;6(2):135-51. doi: 10.2165/00003088-198106020-00004.
4 The metabolism of probenecid in man Ann N Y Acad Sci. 1971 Jul 6;179:399-402. doi: 10.1111/j.1749-6632.1971.tb46916.x.

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