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

General Information of Drug (ID: DR1611)
Drug Name
Tolazamide
Synonyms
Tolanase; Tolazamida; Tolazamida [INN-Spanish]; Tolazamidum; Tolazamidum [INN-Latin]; Tolazolamide; Tolinase; U 17835; U-17835; Diabewas; Norglycin; tolazamide; 1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylurea; 1-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; 1156-19-0; 4-(p-Tolylsulfonyl)-1,1-hexamethylenesemicarbazide; CCRIS 591; EINECS 214-588-3; N-(p-Toluenesulfonyl)-N'-hexamethyleniminourea; NCI-C03327; NSC-70762; UNII-9LT1BRO48Q; Urea, 1-(hexahydroazepin-1-yl)-3-p-tolylsulfonyl-
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 311.4 Topological Polar Surface Area 86.9
Heavy Atom Count 21 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5503
PubChem SID
114000 ; 221319 ; 855941 ; 3277020 ; 5657915 ; 7847445 ; 7980809 ; 8149777 ; 8153383 ; 10321805 ; 11111869 ; 11111870 ; 11120085 ; 11120573 ; 11121061 ; 11121570 ; 11122050 ; 11147168 ; 11335387 ; 11360626 ; 11362639 ; 11364163 ; 11365201 ; 11366725 ; 11367763 ; 11369287 ; 11370549 ; 11370550 ; 11372624 ; 11373364 ; 11374078 ; 11375925 ; 11377449 ; 11455805 ; 11461598 ; 11466582 ; 11467702 ; 11485053 ; 11486284 ; 11489265 ; 11491288 ; 11492055 ; 11495083 ; 14850072 ; 17405749 ; 24277741 ; 26537486 ; 26612233 ; 26680152 ; 26747047
ChEBI ID
CHEBI:9613
CAS Number
1156-19-0
TTD Drug ID
D09FJB
Formula
C14H21N3O3S
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NN2CCCCCC2
InChI
1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18)
InChIKey
OUDSBRTVNLOZBN-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
1-(4-hydroxyhexahydroazepin-1-yl)-3-p-tolylsulfonylurea DM006304
5503
Unclear 1 [4]
1-(hexahydroazepin-1-yl)-3-p-(carboxyphenyl)sulfonylurea DM006307
91800157
Unclear 1 [4]
1-(hexahydroazepin-1-yl)-3-p-(hydroxymethylphenyl)sulfonylurea DM006306
91800178
Other reaction - Hydroxymethylation 1 [4]
p-toluenesulfonamide DM006305
6269
Unclear 1 [4]
1-(hexahydroazepin-1-yl)-3-p-(carboxyphenyl)sulfonylurea DM006307
91800157
Unclear 2 [4]
p-toluenesulfonamide DM006305
6269
Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006769 Tolazamide 1-(4-hydroxyhexahydroazepin-1-yl)-3-p-tolylsulfonylurea Unclear Unclear [4]
MR006771 Tolazamide 1-(hexahydroazepin-1-yl)-3-p-(hydroxymethylphenyl)sulfonylurea Other reaction - Hydroxymethylation Unclear [4]
MR006773 Tolazamide p-toluenesulfonamide Unclear Unclear [4]
MR006774 Tolazamide 1-(hexahydroazepin-1-yl)-3-p-(carboxyphenyl)sulfonylurea Unclear Unclear [4]
MR006770 1-(4-hydroxyhexahydroazepin-1-yl)-3-p-tolylsulfonylurea p-toluenesulfonamide Unclear Unclear [4]
MR006772 1-(hexahydroazepin-1-yl)-3-p-(hydroxymethylphenyl)sulfonylurea 1-(hexahydroazepin-1-yl)-3-p-(carboxyphenyl)sulfonylurea Unclear Unclear [4]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1376 Bacteroides ovatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1431 Holdemanella biformis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [3]
⏷ Show the Full List of 21  DME(s)
References
1 Tolazamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinically and pharmacologically relevant interactions of antidiabetic drugs. Ther Adv Endocrinol Metab. 2016 Apr;7(2):69-83.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Metabolic fate of tolazamide in man and in the rat

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