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

General Information of Drug (ID: DR1163)
Drug Name
Nintedanib esylate
Synonyms
Nintedanib Esilate; Nintedanib Esylate(BIBF-1120); Nintedanib Ethanesulfonate Salt; Nintedanib esylate; Nintedanib ethanesulfonate; SCHEMBL2278759; SCHEMBL753253; (3Z)-2,3-Dihydro-3-[[[4-[methyl[2-(4-methyl-1-piperazinyl)acetyl]amino]phenyl]amino]phenylmethylene]-2-oxo-1H-indole-6-carboxylic acid methyl ester ethanesulfonate; 42F62RTZ4G; 656247-18-6; AKOS025149444; BCP09963; BIBF 1120 (esylate); BIBF 1120 esylate; CHEBI:85170; CHEMBL3039504; DTXSID40215873; KS-00000LA8; MFCD26142360; NSC753000; UNII-42F62RTZ4G
Indication Idiopathic pulmonary fibrosis [ICD11: CB03] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 649.8 Topological Polar Surface Area 164
Heavy Atom Count 46 Rotatable Bond Count 9
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
135476717
ChEBI ID
CHEBI:85170
CAS Number
656247-18-6
TTD Drug ID
D0FO7G
Formula
C33H39N5O7S
Canonical SMILES
CCS(=O)(=O)O.CN1CCN(CC1)CC(=O)N(C)C2=CC=C(C=C2)N=C(C3=CC=CC=C3)C4=C(NC5=C4C=CC(=C5)C(=O)OC)O
InChI
1S/C31H33N5O4.C2H6O3S/c1-34-15-17-36(18-16-34)20-27(37)35(2)24-12-10-23(11-13-24)32-29(21-7-5-4-6-8-21)28-25-14-9-22(31(39)40-3)19-26(25)33-30(28)38;1-2-6(3,4)5/h4-14,19,33,38H,15-18,20H2,1-3H3;2H2,1H3,(H,3,4,5)
InChIKey
ZNMRDZZRAFJOKY-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
Nintedanib metabolite M12 DM002246
135461281
Unclear 1 [3]
Nintedanib metabolite M13 DM002250 N. A. Unclear 1 [3]
Nintedanib metabolite M5 DM002239 N. A. Oxidation - Demethylation 1 [3]
Nintedanib metabolite M6 DM020023
135837936
Oxidation - Demethylation 1 [3]
Nintedanib metabolite M7 DM002245 N. A. Conjugation - Glucuronidation 1 [3]
Nintedanib metabolite M8 DM002248 N. A. Oxidation - Hydroxylation 1 [3]
Nintedanib metabolite M9 DM002247
138462685
Unclear 1 [3]
Nintedanib metabolite M1 DM002241 N. A. Oxidation - Hydroxylation 2 [3]
Nintedanib metabolite M10 DM002240 N. A. Oxidation - Decarbonylation 2 [3]
Nintedanib metabolite M11 DM002244 N. A. Reduction - Reduction; Glycine addition 2 [3]
Nintedanib metabolite M14 DM002243 N. A. Conjugation - Glucuronidation 2 [3]
Nintedanib metabolite M15 DM002235 N. A. Conjugation - Glucuronidation 2 [3]
Nintedanib metabolite M18 DM002234 N. A. Conjugation - Acetylation 2 [3]
Nintedanib metabolite M2 DM002242 N. A. Oxidation - Hydroxylation 2 [3]
Nintedanib metabolite M3 DM002236 N. A. Oxidation - Hydroxylation 2 [3]
Nintedanib metabolite M4 DM002231
156614011
Oxidation - Demethylation 2 [3]
Nintedanib metabolite M16 DM002233 N. A. Conjugation - Acetylation 3 [3]
⏷ Show the Full List of 17  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003531 Nintedanib esylate Nintedanib metabolite M6 Oxidation - Demethylation CYP2C8 ... [3]
MR003537 Nintedanib esylate Nintedanib metabolite M5 Oxidation - Demethylation CYP1A1 [3]
MR003543 Nintedanib esylate Nintedanib metabolite M7 Conjugation - Glucuronidation [3]
MR003544 Nintedanib esylate Nintedanib metabolite M12 Unclear CYP3A4 [3]
MR003545 Nintedanib esylate Nintedanib metabolite M9 Unclear [3]
MR003546 Nintedanib esylate Nintedanib metabolite M8 Oxidation - Hydroxylation CYP3A4 ... [3]
MR003547 Nintedanib esylate Nintedanib metabolite M13 Unclear CYP3A4 ... [3]
MR003538 Nintedanib metabolite M5 Nintedanib metabolite M10 Oxidation - Decarbonylation [3]
MR003539 Nintedanib metabolite M5 Nintedanib metabolite M1 Oxidation - Hydroxylation [3]
MR003540 Nintedanib metabolite M5 Nintedanib metabolite M2 Oxidation - Hydroxylation [3]
MR003541 Nintedanib metabolite M5 Nintedanib metabolite M14 Conjugation - Glucuronidation [3]
MR003542 Nintedanib metabolite M5 Nintedanib metabolite M11 Reduction - Reduction; Glycine addition [3]
MR003532 Nintedanib metabolite M6 Nintedanib metabolite M4 Oxidation - Demethylation [3]
MR003534 Nintedanib metabolite M6 Nintedanib metabolite M18 Conjugation - Acetylation [3]
MR003535 Nintedanib metabolite M6 Nintedanib metabolite M15 Conjugation - Glucuronidation [3]
MR003536 Nintedanib metabolite M6 Nintedanib metabolite M3 Oxidation - Hydroxylation [3]
MR003533 Nintedanib metabolite M6 Nintedanib metabolite M16 Conjugation - Acetylation [3]
⏷ Show the Full List of 17 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
References
1 Nintedanib Esylate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics and pharmacodynamics of nintedanib. Clin Pharmacokinet. 2019 Sep;58(9):1131-1147.
3 Metabolic pro?ling of tyrosine kinase inhibitor nintedanib using metabolomics J Pharm Biomed Anal. 2020 Feb 20;180:113045. doi: 10.1016/j.jpba.2019.113045.

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