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

General Information of Drug (ID: DR0423)
Drug Name
Dasatinib
Synonyms
Dasatinib; Dasatinib (BMS-354825); Dasatinib (anhydrous); Dasatinib [USAN]; Sprycel; anh. dasatinib; anhydrous dasatinib; dasatinib (anh.); dasatinibum; 302962-49-8; BMS 354825; BMS Dasatinib; BMS-354825; BMS354825; N-(2-CHLORO-6-METHYLPHENYL)-2-({6-[4-(2-HYDROXYETHYL)PIPERAZIN-1-YL]-2-METHYLPYRIMIDIN-4-YL}AMINO)-1,3-THIAZOLE-5-CARBOXAMIDE; N-(2-chloro-6-methylphenyl)-2-(6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)thiazole-5-carboxamide; UNII-X78UG0A0RN
Indication Chronic myelogenous leukaemia [ICD11: 2A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 488 Topological Polar Surface Area 135
Heavy Atom Count 33 Rotatable Bond Count 7
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
3062316
PubChem SID
10061134 ; 12015788 ; 14859389 ; 17397755 ; 17422520 ; 36127155 ; 46505143 ; 46513626 ; 47883136 ; 48429642 ; 49742622 ; 50070229 ; 50070567 ; 50071309 ; 50100097 ; 50125840 ; 52995488 ; 53799228 ; 56312240 ; 56312839 ; 56313127 ; 56373968 ; 56459420 ; 57288451 ; 57354110 ; 57551950 ; 74374210 ; 85246174 ; 87235888 ; 87357382 ; 93581026 ; 99381604 ; 99437986 ; 103501621 ; 103905543 ; 111644212 ; 117418208 ; 117695728 ; 118050493 ; 119503515 ; 124361516 ; 124756940 ; 124893650 ; 124893651 ; 124893652 ; 125001912 ; 125163747 ; 125264620 ; 125347447 ; 126624063
ChEBI ID
ChEBI:49375
CAS Number
302962-49-8
TTD Drug ID
D0E6XR
Formula
C22H26ClN7O2S
Canonical SMILES
CC1=C(C(=CC=C1)Cl)NC(=O)C2=CN=C(S2)NC3=CC(=NC(=N3)C)N4CCN(CC4)CCO
InChI
1S/C22H26ClN7O2S/c1-14-4-3-5-16(23)20(14)28-21(32)17-13-24-22(33-17)27-18-12-19(26-15(2)25-18)30-8-6-29(7-9-30)10-11-31/h3-5,12-13,31H,6-11H2,1-2H3,(H,28,32)(H,24,25,26,27)
InChIKey
ZBNZXTGUTAYRHI-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
Dasatinib metabolite M20 DM001915
11854533
Oxidation - Hydroxylation 1 [3]
Dasatinib metabolite M24 DM001916
11854534
Oxidation - Hydroxylation 1 [3]
Dasatinib metabolite M4 DM001912
11669430
Oxidation - N-Dealkylation 1 [3]
Dasatinib metabolite M5 DM001913
11854535
Oxidation - N-Oxidation 1 [3] , [5]
Dasatinib metabolite M6 DM001914
11854012
Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000744 Dasatinib Dasatinib metabolite M4 Oxidation - N-Dealkylation CYP3A4 [3]
MR000745 Dasatinib Dasatinib metabolite M5 Oxidation - N-Oxidation FMO3 [3], [5]
MR000746 Dasatinib Dasatinib metabolite M6 Unclear Unclear [3]
MR000747 Dasatinib Dasatinib metabolite M20 Oxidation - Hydroxylation CYP3A4 [3]
MR000748 Dasatinib Dasatinib metabolite M24 Oxidation - Hydroxylation CYP3A4 [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1435 Lactobacillus reuteri Not Available Not Available [4]
⏷ Show the Full List of 10  DME(s)
References
1 Dasatinib was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics of tyrosine kinase inhibitors. Cancer Treat Rev. 2009 Dec;35(8):692-706.
3 Identification of the human enzymes involved in the oxidative metabolism of dasatinib: an effective approach for determining metabolite formation kinetics. Drug Metab Dispos. 2008 Sep;36(9):1828-39.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Production of drug metabolites by human FMO3 in Escherichia coli Microb Cell Fact. 2020 Mar 20;19(1):74. doi: 10.1186/s12934-020-01332-1.

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