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

General Information of Drug (ID: DR4012)
Drug Name
Motesanib
Synonyms N-(2,3-dihydro-3,3-dimethyl-1H-indol-6-yl)-2-((4-pyridinylmethyl)amino)-3-pyridinecarboxamide; N-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-2-[(pyridin-4-ylmethyl)amino]pyridine-3-carboxamide
Indication Lung cancer [ICD11: 2C25] Discontinued in Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 373.5 Topological Polar Surface Area 78.9
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
11667893
ChEBI ID
CHEBI:51098
CAS Number
453562-69-1
TTD Drug ID
D00DQX
Formula
C22H23N5O
Canonical SMILES
CC1(CNC2=C1C=CC(=C2)NC(=O)C3=C(N=CC=C3)NCC4=CC=NC=C4)C
InChI
InChI=1S/C22H23N5O/c1-22(2)14-26-19-12-16(5-6-18(19)22)27-21(28)17-4-3-9-24-20(17)25-13-15-7-10-23-11-8-15/h3-12,26H,13-14H2,1-2H3,(H,24,25)(H,27,28)
InChIKey
RAHBGWKEPAQNFF-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
Motesanib M1 DM016827
156596536
Conjugation - Glucuronidation 1 [2]
Motesanib M3 DM015674
10408013
Unclear - Unclear 1 [2]
Motesanib M4 DM016814
156028127
Unclear - Unclear 1 [2] , [3]
Motesanib M5 DM016815
156028128
Oxidation - Hydroxylation 1 [2]
Motesanib Ma DM016753
154572896
Unclear - Unclear 1 [2]
Motesanib Mb DM017973 N. A. Unclear - Unclear 1 [2]
Motesanib Mv DM016748
153999995
Unclear - Unclear 1 [2]
Motesanib Mx DM001009
5922
Unclear - Unclear 1 [2]
Motesanib M4 DM016814
156028127
Unclear - Unclear 2 [2]
Motesanib Miv DM016822
156596415
Unclear - Unclear 2 [2]
Motesanib Miv DM016822
156596415
Unclear - Unclear 3 [2]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009723 Motesanib Motesanib M5 Oxidation - Hydroxylation CYP3A4 ... [2]
MR009726 Motesanib Motesanib M4 Unclear - Unclear CYP3A4 ... [2], [3]
MR009727 Motesanib Motesanib Mv Unclear - Unclear Unclear [2]
MR009729 Motesanib Motesanib Ma Unclear - Unclear Unclear [2]
MR009730 Motesanib Motesanib Mb Unclear - Unclear Unclear [2]
MR009731 Motesanib Motesanib M1 Conjugation - Glucuronidation UGT1A1 ... [2]
MR009732 Motesanib Motesanib M3 Unclear - Unclear CYP3A4 ... [2]
MR009733 Motesanib Motesanib Mx Unclear - Unclear Unclear [2]
MR009724 Motesanib M5 Motesanib M4 Unclear - Unclear Unclear [2]
MR009728 Motesanib Mv Motesanib Miv Unclear - Unclear Unclear [2]
MR009725 Motesanib M4 Motesanib Miv Unclear - Unclear Unclear [2]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5660).
2 In vitro metabolism of the novel, highly selective oral angiogenesis inhibitor motesanib diphosphate in preclinical species and in humans
3 Population pharmacokinetic modeling of motesanib and its active metabolite, M4, in cancer patients

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