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

General Information of Drug (ID: DR1509)
Drug Name
Sulfadiazine
Synonyms
Sanodiazine; Spofadrizine; Sterazine; Sulfadiazene; Sulfadiazin; Sulfanilamidopyrimidine; Sulfapyrimidin; Sulfapyrimidine; Sulfatryl; Sulfazine; Sulfolex; Sulfonsol; Sulfose; Sulphadiazine; Terfonyl; Theradiazine; Tri-Sulfameth; Trifonamide; Adiazin; Adiazine; Cremodiazine; Cremotres; Debenal; Deltazina; Diazin; Diazolone; Diazyl; Eskadiazine; Honey diazine; Lipo-Levazine; Liquadiazine; Microsulfon; Neazine; Neotrizine; Palatrize; Piridisir; Pirimal; Pyrimal; Quadetts; Quadramoid; Trisem; Truozine; sulfadiazine; 2-Sulfanilamidopyrimidine; 68-35-9
Indication Toxoplasmosis [ICD11: 1F57] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 250.28 Topological Polar Surface Area 106
Heavy Atom Count 17 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
5215
PubChem SID
9860 ; 92611 ; 602777 ; 642441 ; 642967 ; 855872 ; 933844 ; 3182910 ; 4484320 ; 7847653 ; 7980699 ; 8149533 ; 8153205 ; 10321441 ; 10532663 ; 11112193 ; 11335718 ; 11360957 ; 11363880 ; 11366442 ; 11369004 ; 11372203 ; 11373882 ; 11377166 ; 11461929 ; 11466051 ; 11467171 ; 11485153 ; 11485742 ; 11489135 ; 11491177 ; 11492157 ; 11494800 ; 11533903 ; 14749834 ; 24861734 ; 24899802 ; 25623038 ; 26611925 ; 26679790 ; 26747022 ; 26747023 ; 29224272 ; 46506164 ; 47216749 ; 47440219 ; 47588965 ; 47662250 ; 47736446 ; 47885378
ChEBI ID
ChEBI:9328
CAS Number
68-35-9
TTD Drug ID
D05LKP
Formula
C10H10N4O2S
Canonical SMILES
C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N
InChI
1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)
InChIKey
SEEPANYCNGTZFQ-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
4-Hydroxysulfadiazine DM006376
462433
Unclear 1 [5]
5-Hydroxysulfadiazine DM006377
462434
Unclear 1 [5]
Sulfadiazine hydroxylamine DM006375
45028334
Multi-steps Reaction - Hydrolyzationn; sulfadiazine acetylation 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006846 Sulfadiazine Sulfadiazine hydroxylamine Multi-steps Reaction - Hydrolyzationn; sulfadiazine acetylation CYP2C8 ... [5]
MR006848 4-Hydroxysulfadiazine 5-Hydroxysulfadiazine Unclear Unclear [5]
MR006847 Sulfadiazine hydroxylamine 4-Hydroxysulfadiazine Unclear Unclear [5]
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
[3]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
Methylenetetrahydrofolate reductase (MTHFR) DME0083 Homo sapiens
MTHR_HUMAN
1.5.1.20
[5]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[5]
RNA cytidine acetyltransferase (hALP) DME0007 Homo sapiens
NAT10_HUMAN
2.3.1.5
[5]
⏷ Show the Full List of 8  DME(s)
References
1 Sulfadiazine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Reduction of sulfamethoxazole and dapsone hydroxylamines by a microsomal enzyme system purified from pig liver and pig and human liver microsomes. Life Sci. 2005 May 27;77(2):205-19.
3 Prediction of in vivo drug-drug interactions between tolbutamide and various sulfonamides in humans based on in vitro experiments. Drug Metab Dispos. 2000 Apr;28(4):475-81.
4 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
5 Identification of cytochrome P450 and arylamine N-acetyltransferase isoforms involved in sulfadiazine metabolism. Drug Metab Dispos. 2005 Jul;33(7):969-76.

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