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

General Information of Drug (ID: DR0415)
Drug Name
Dapsone
Synonyms
Dapson; Dapsonum; Diaphenylsulfon; Diaphenylsulfone; Diaphenylsulphon; Diaphenylsulphone; Diphenasone; Diphone; Disulone; Dubronax; Dumitone; Eporal; Metabolite C; Novophone; Sulfadione; Sulfona; Sulfona-MAE; Sulphadione; Sulphonyldianiline; Aczone; Avlosulfon; Avlosulfone; Avlosulphone; Bis(4-aminophenyl) sulfone; Croysulfone; Croysulphone; Sumicure S; Tarimyl; Udolac; dapsone; p-Aminophenyl sulfone; 4,4'-Diaminodiphenyl sulfone; 4,4'-Diaminodiphenylsulfone; 4,4'-Sulfonyldianiline; 4-Aminophenyl sulfone; 80-08-0; DADPS
Indication Pneumocystis pneumonia [ICD11: CA40] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 248.3 Topological Polar Surface Area 94.6
Heavy Atom Count 17 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2955
PubChem SID
9868 ; 72086 ; 601388 ; 855979 ; 866561 ; 3172497 ; 3293541 ; 4280275 ; 7847658 ; 7979025 ; 8149283 ; 8151886 ; 10321253 ; 10536207 ; 11112211 ; 11142519 ; 11335748 ; 11360987 ; 11363782 ; 11366344 ; 11368906 ; 11371449 ; 11374039 ; 11377068 ; 11461959 ; 11466063 ; 11467183 ; 11484761 ; 11485786 ; 11488949 ; 11490191 ; 11492125 ; 11494702 ; 15196656 ; 17389950 ; 24714727 ; 24859802 ; 24869870 ; 24891242 ; 26611685 ; 26679780 ; 26747072 ; 26747073 ; 26751585 ; 29222105 ; 46505300 ; 47588972 ; 47736452 ; 47736453 ; 47885386
ChEBI ID
CHEBI:4325
CAS Number
80-08-0
TTD Drug ID
D0MA9N
Formula
C12H12N2O2S
Canonical SMILES
C1=CC(=CC=C1N)S(=O)(=O)C2=CC=C(C=C2)N
InChI
1S/C12H12N2O2S/c13-9-1-5-11(6-2-9)17(15,16)12-7-3-10(14)4-8-12/h1-8H,13-14H2
InChIKey
MQJKPEGWNLWLTK-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
Dapsone hydroxylamine DM001881
65387
Oxidation - N-Hydroxylation 1 [7]
Monoacetyldapsone DM001885
11257
Unclear 1 [8]
Nitroso-dapsone DM001882
132146770
Oxidation - Oxidation 2 [7]
Dapsone mercaptal intermediate DM001883 N. A. Conjugation - Glutathione Conjugation 3 [7]
Dapsone GSH conjugate metabolite DM001884 N. A. Other reaction - Spontaneous 4 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000733 Dapsone Dapsone hydroxylamine Oxidation - N-Hydroxylation CYP3A4 ... [7]
MR000734 Dapsone Monoacetyldapsone Unclear NAT2 [8]
MR000730 Dapsone hydroxylamine Nitroso-dapsone Oxidation - Oxidation Unclear [7]
MR000731 Nitroso-dapsone Dapsone mercaptal intermediate Conjugation - Glutathione Conjugation Unclear [7]
MR000732 Dapsone mercaptal intermediate Dapsone GSH conjugate metabolite Other reaction - Spontaneous Unclear [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome c oxidase subunit 2 (MT-CO2) DMEN086 Homo sapiens
COX2_HUMAN
4.3.2.1
[2]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[6]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
Myeloperoxidase (MPO) DME0096 Homo sapiens
PERM_HUMAN
1.11.2.2
[7]
N-acetyltransferase 2 (NAT2) DME0051 Homo sapiens
ARY2_HUMAN
2.3.1.5
[8]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[7]
Prostaglandin G/H synthase 2 (COX-2) DME0114 Homo sapiens
PGH2_HUMAN
1.14.99.1
[7]
⏷ Show the Full List of 13  DME(s)
References
1 Dapsone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 CYP2C8/9 mediate dapsone N-hydroxylation at clinical concentrations of dapsone. Drug Metab Dispos. 2000 Aug;28(8):865-8.
4 Differential activation of CYP2C9 variants by dapsone. Biochem Pharmacol. 2004 May 15;67(10):1831-41.
5 Metabolic interactions of putative cytochrome P4503A substrates with alternative pathways of dapsone metabolism in human liver microsomes. Drug Metab Dispos. 1996 Feb;24(2):164-171.
6 Drug Interactions Flockhart Table
7 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.
8 High plasma homocysteine levels contribute to the risk of stroke recurrence and all-cause mortality in a large prospective stroke population Clin Sci (Lond). 2009 Oct 26;118(3):187-94. doi: 10.1042/CS20090142.

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