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

General Information of Drug (ID: DR1519)
Drug Name
Sunitinib malate
Synonyms
Sunitinib malate [USAN]; Sunitinib; Sunitinib Base; UNII-V99T50803M; V99T50803M; sunitinibum; 342641-94-5; 557795-19-4; CHEBI:38940; CHEMBL535; N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide; N-[2-(diethylamino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide; NSC750690; SU11248; Su-011248; UNII-LVX8N1UT73; (Z)-N-(2-(diethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (S)-2-hydroxysuccinate; 341031-54-7; LVX8N1UT73; MFCD08282795; N-(2-(Diethylamino)ethyl)-5-((Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (2S)-hydroxybutanedioate; PHA-290940AD; SU 011248; SU010398; SU011248; SU011248 L-malate salt; SUNITINIB MALEATE
Indication Renal cell carcinoma [ICD11: 2C90] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 532.6 Topological Polar Surface Area 172
Heavy Atom Count 38 Rotatable Bond Count 10
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
6456015
CAS Number
341031-54-7
TTD Drug ID
D0R0MW
Formula
C26H33FN4O7
Canonical SMILES
CCN(CC)CCNC(=O)C1=C(NC(=C1C)C=C2C3=C(C=CC(=C3)F)NC2=O)C.C(C(C(=O)O)O)C(=O)O
InChI
1S/C22H27FN4O2.C4H6O5/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28;5-2(4(8)9)1-3(6)7/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28);2,5H,1H2,(H,6,7)(H,8,9)/b17-12-;/t;2-/m.0/s1
InChIKey
LBWFXVZLPYTWQI-IPOVEDGCSA-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
SU12662 DM000397
10292573
Oxidation - Deethylation 1 [6]
Sun-SG DM017435 N. A. Unclear - Unclear 1 [7]
Sunitinib malate Metabolite M11 DM016209
59069527
Unclear - Unclear 1 [7]
Sunitinib malate Metabolite M2E DM015643
10273227
Unclear - Unclear 1 [7]
Sunitinib malate Metabolite M2F DM016210
59069542
Unclear - Unclear 1 [7]
Sunitinib malate Metabolite M3 DM015739
11221549
Oxidation - Bis-deethylation 1 [7]
Sunitinib malate Metabolite M4E DM016538
118753424
Unclear - Unclear 1 [7]
Sunitinib malate Metabolite M8 DM016318
71540360
Reduction - Reduction 1 [7] , [3]
Sunitinib malate Metabolite M9 DM015447
5329102
Unclear - Unclear 1 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008644 Sunitinib malate SU12662 Oxidation - Deethylation CYP3A4 [6]
MR008645 Sunitinib malate Sunitinib malate Metabolite M11 Unclear - Unclear Unclear [7]
MR008646 Sunitinib malate Sunitinib malate Metabolite M9 Unclear - Unclear Unclear [7]
MR008647 Sunitinib malate Sunitinib malate Metabolite M8 Reduction - Reduction CYP1A2 ... [7], [3]
MR008648 Sunitinib malate Sunitinib malate Metabolite M2F Unclear - Unclear Unclear [7]
MR008649 Sunitinib malate Sunitinib malate Metabolite M3 Oxidation - Bis-deethylation Unclear [7]
MR008650 Sunitinib malate Sunitinib malate Metabolite M2E Unclear - Unclear Unclear [7]
MR008651 Sunitinib malate Sunitinib malate Metabolite M4E Unclear - Unclear Unclear [7]
MR008652 Sunitinib malate Sun-SG Unclear - Unclear Unclear [7]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A (CYP1A) DMEN074 . Not Available Not Available [2]
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[]
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
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
⏷ Show the Full List of 9  DME(s)
References
1 Sunitinib Malate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Acute pancreatitis in a patient treated with imatinib and gefitinib. J Oncol Pharm Pract. 2021 Jun;27(4):980-983. doi: 10.1177/1078155220949639.
3 Cytochromes P450 1A2 and 3A4 Catalyze the Metabolic Activation of Sunitinib
4 In vitro assessment of time-dependent inhibitory effects on CYP2C8 and CYP3A activity by fourteen protein kinase inhibitors. Drug Metab Dispos. 2014 Jul;42(7):1202-9.
5 Drug Interactions Flockhart Table
6 Sunitinib malate for the treatment of metastatic renal cell carcinoma and gastrointestinal stromal tumors
7 Pharmacokinetics, distribution, and metabolism of [14C]sunitinib in rats, monkeys, and humans

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