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

General Information of Drug (ID: DR0249)
Drug Name
Busulfan
Synonyms
Busulfano; Busulfanum; Busulfex; Busulphan; Busulphane; Buzulfan; Citosulfan; Leucosulfan; Mablin; Mielevcin; Mielosan; Mielucin; Milecitan; Mileran; Misulban; Mitostan; Myeleukon; Myeloleukon; Myelosan; Myelosanum; Mylecytan; Myleran; Sulfabutin; Sulphabutin; busulfan; butane-1,4-diyl dimethanesulfonate; 1,4-BUTANEDIOL DIMETHANESULFONATE; 1,4-Butanediol, dimethanesulfonate; 1,4-Dimesyloxybutane; 1,4-Dimethanesulfonoxybutane; 1,4-Dimethanesulfonyloxybutane; 1,4-Dimethylsulfonyloxybutane; 55-98-1; Tetramethylene dimethane sulfonate
Indication Chronic myelogenous leukaemia [ICD11: 2A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 246.3 Topological Polar Surface Area 104
Heavy Atom Count 14 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
2478
PubChem SID
9080 ; 67633 ; 219854 ; 3152242 ; 4652645 ; 7847314 ; 7978829 ; 8136888 ; 8149226 ; 8151654 ; 10321898 ; 11336022 ; 11361261 ; 11362926 ; 11365488 ; 11368050 ; 11371520 ; 11373837 ; 11376212 ; 11445992 ; 11446841 ; 11462233 ; 11483989 ; 11487883 ; 11490136 ; 11492074 ; 11493906 ; 11533211 ; 15221088 ; 17388889 ; 17389813 ; 24891664 ; 26611631 ; 26679765 ; 26747279 ; 26747280 ; 26747281 ; 26752840 ; 29221642 ; 46506234 ; 47365244 ; 47440312 ; 47440313 ; 48414081 ; 48415668 ; 48423740 ; 48424910 ; 48425335 ; 49648470 ; 49855504
ChEBI ID
ChEBI:28901
CAS Number
55-98-1
TTD Drug ID
D07SUG
Formula
C6H14O6S2
Canonical SMILES
CS(=O)(=O)OCCCCOS(=O)(=O)C
InChI
1S/C6H14O6S2/c1-13(7,8)11-5-3-4-6-12-14(2,9)10/h3-6H2,1-2H3
InChIKey
COVZYZSDYWQREU-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
Busulfan metabolite M6 DM000711
8028
Unclear 1 [7]
Sulfoniumion of glutathione DM000706 N. A. Unclear 1 [8]
Tetrahydrothiophene DM000707
1127
Unclear 2 [8]
Busulfan metabolite M4 DM000708
1128
Oxidation - Oxidation 3 [8]
Busulfan metabolite M5 DM000709
31347
Oxidation - Oxidation 4 [8]
Busulfan metabolite M3 DM000710
98932
Oxidation - Hydroxylation 5 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000531 Busulfan Sulfoniumion of glutathione Unclear GSTA1 [8]
MR000532 Busulfan Busulfan metabolite M6 Unclear Unclear [7]
MR000527 Sulfoniumion of glutathione Tetrahydrothiophene Unclear Unclear [8]
MR000528 Tetrahydrothiophene Busulfan metabolite M4 Oxidation - Oxidation Unclear [8]
MR000529 Busulfan metabolite M4 Busulfan metabolite M5 Oxidation - Oxidation Unclear [8]
MR000530 Busulfan metabolite M5 Busulfan metabolite M3 Oxidation - Hydroxylation Unclear [8]
⏷ 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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Glutathione S-transferase alpha-1 (GSTA1) DME0011 Homo sapiens
GSTA1_HUMAN
2.5.1.18
[3]
Glutathione S-transferase alpha-2 (GSTA2) DME0081 Homo sapiens
GSTA2_HUMAN
2.5.1.18
[4]
Glutathione S-transferase mu-1 (GSTM1) DME0308 Homo sapiens
GSTM1_HUMAN
2.5.1.18
[5]
Glutathione S-transferase pi (GSTP1) DME0088 Homo sapiens
GSTP1_HUMAN
2.5.1.18
[5]
Microsomal glutathione S-transferase 2 (MGST2) DME0089 Homo sapiens
MGST2_HUMAN
2.5.1.18
[6]
⏷ Show the Full List of 6  DME(s)
References
1 Busulfan was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Update: clinically significant cytochrome P-450 drug interactions. Pharmacotherapy. 1998 Jan-Feb;18(1):84-112.
3 Glutathione S-transferase M1 polymorphism: a risk factor for hepatic venoocclusive disease in bone marrow transplantation. Blood. 2004 Sep 1;104(5):1574-7.
4 Endothelial cells do not express GSTA1: potential relevance to busulfan-mediated endothelial damage during haematopoietic stem cell transplantation. Eur J Haematol. 2008 Apr;80(4):299-302.
5 Busulfan conjugation by glutathione S-transferases alpha, mu, and pi. Drug Metab Dispos. 1996 Sep;24(9):1015-9.
6 Overexpression of glutathione-S-transferase, MGSTII, confers resistance to busulfan and melphalan. Cancer Invest. 2005;23(1):19-25.
7 U. S. FDA Label -Busulfan
8 Urinary metabolites of busulfan in the rat Drug Metab Dispos. 1987 May-Jun;15(3):399-402.

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