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

General Information of Drug (ID: DR1511)
Drug Name
Sulfamethoxazole
Synonyms
Simsinomin; Sinomin; Solfametossazolo; Sulfamethalazole; Sulfamethoxazol; Sulfamethoxazolum; Sulfamethoxizole; Sulfamethylisoxazole; Sulfametoxazol; Sulfisomezole; Sulpha-methoxizole; Sulphamethoxazol; Sulphamethoxazole; Sulphamethylisoxazole; Sulphisomezole; Urobak; Azo-gantanol; Bactrimel; Gamazole; Gantanol; Gantanol-DS; Metoxal; Radonil; Ro 4-2130; sulfamethoxazole; 3-Sulfanilamido-5-methylisoxazole; 4-Amino-N-(5-methyl-3-isoxazolyl)benzenesulfonamide; 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide; 723-46-6
Indication Infectious cystitis [ICD11: GC00] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 253.28 Topological Polar Surface Area 107
Heavy Atom Count 17 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5329
PubChem SID
9523 ; 430150 ; 602530 ; 855654 ; 3160889 ; 4484561 ; 7847513 ; 7980702 ; 8149537 ; 8153272 ; 10321458 ; 10533933 ; 10589657 ; 11112438 ; 11335824 ; 11361063 ; 11363888 ; 11366450 ; 11369012 ; 11371628 ; 11373888 ; 11377174 ; 11385461 ; 11462035 ; 11466205 ; 11467325 ; 11484632 ; 11485730 ; 11488604 ; 11490400 ; 11492160 ; 11494808 ; 14718462 ; 14798729 ; 17388720 ; 24870521 ; 24899752 ; 25623303 ; 26611929 ; 26679802 ; 26746946 ; 26746947 ; 29224383 ; 46508111 ; 47188230 ; 47216775 ; 47291127 ; 47365185 ; 47440251 ; 47662281
ChEBI ID
ChEBI:9332
CAS Number
723-46-6
TTD Drug ID
D0R9OH
Formula
C10H11N3O3S
Canonical SMILES
CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI
1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
InChIKey
JLKIGFTWXXRPMT-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
5-hydroxysulfamethoxazole DM000372
10355717
Oxidation - 5-Hydroxylation 1 [5]
N-acetylsulfamethoxazole DM000374
65280
Conjugation - Acetylation 1 [5]
Sulfamethoxazole N-glucuronide DM000375 N. A. Conjugation - N-Glucuronidation 1 [5]
Sulfamethoxazole N4-hydroxylamine DM000369
114821
Oxidation - N-Hydroxylation 1 [5] , [2] , [3]
N4-Acetyl-5-OH-sulfamethoxazole DM000373 N. A. Oxidation - 5-Hydroxylation 2 [5]
N4-Acetyl-5-OH-sulfamethoxazole DM000373 N. A. Conjugation - Acetylation 2 [5]
Nitroso-sulfamethoxazole DM000370 N. A. Unclear 2 [5]
Sulfamethoxazole GSH conjugate DM000371 N. A. Unclear 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002280 Sulfamethoxazole Sulfamethoxazole N4-hydroxylamine Oxidation - N-Hydroxylation CYP3A4 ... [5], [2], [3]
MR002281 Sulfamethoxazole 5-hydroxysulfamethoxazole Oxidation - 5-Hydroxylation Unclear [5]
MR002282 Sulfamethoxazole N-acetylsulfamethoxazole Conjugation - Acetylation NAT1 ... [5]
MR002283 Sulfamethoxazole Sulfamethoxazole N-glucuronide Conjugation - N-Glucuronidation UGT [5]
MR002278 5-hydroxysulfamethoxazole N4-Acetyl-5-OH-sulfamethoxazole Conjugation - Acetylation NAT1 ... [5]
MR002279 N-acetylsulfamethoxazole N4-Acetyl-5-OH-sulfamethoxazole Oxidation - 5-Hydroxylation Unclear [5]
MR002276 Sulfamethoxazole N4-hydroxylamine Nitroso-sulfamethoxazole Unclear Unclear [5]
MR002277 Nitroso-sulfamethoxazole Sulfamethoxazole GSH conjugate Unclear GST [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Myeloperoxidase (MPO) DME0096 Homo sapiens
PERM_HUMAN
1.11.2.2
[4]
N-acetyltransferase 1 (NAT1) DME0050 Homo sapiens
ARY1_HUMAN
2.3.1.5
[4]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[4]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[5]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[6]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[5]
Unclear metabolic mechanism (DME-unclear) DME1288 Shewanella oneidensis Not Available Not Available [7] , [8]
Unclear metabolic mechanism (DME-unclear) DME1468 Synergistetes bacterium Not Available Not Available [9] , [10]
⏷ Show the Full List of 11  DME(s)
References
1 Sulfamethoxazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Sulfamethoxazole and its metabolite nitroso sulfamethoxazole stimulate dendritic cell costimulatory signaling. J Immunol. 2007 May 1;178(9):5533-42.
3 The effect of cimetidine on the formation of sulfamethoxazole hydroxylamine in patients with human immunodeficiency virus. J Clin Pharmacol. 1998 May;38(5):463-6.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development Curr Med Chem. 2009;16(27):3480-675. doi: 10.2174/092986709789057635.
5 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
6 Crystallization and preliminary X-ray characterization of arylamine N-acetyltransferase C (BanatC) from Bacillus anthracis. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Oct 1;63(Pt 10):862-4.
7 Biodegradation of sulfonamides by Shewanella oneidensis MR-1 and Shewanella sp. strain MR-4. Biodegradation. 2018 Apr;29(2):129-140.
8 The 285 kDa Bap/RTX hybrid cell surface protein (SO4317) of Shewanella oneidensis MR-1 is a key mediator of biofilm formation. Res Microbiol. 2010 Mar;161(2):144-52.
9 Bacterial community changes and antibiotic resistance gene quantification in microbial electrolysis cells during long-term sulfamethoxazole treatment. Bioresour Technol. 2019 Dec;294:122170.
10 Distributions of Synergistetes in clinically-healthy and diseased periodontal and peri-implant niches. Microb Pathog. 2016 May;94:90-103.

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