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

General Information of Drug (ID: DR0184)
Drug Name
Belinostat
Synonyms
Beleodaq; Belinostat; Belinostat (PXD101); PX 105684; PX-105684; PX105684; PXD 101; PXD-101; PXD101; (2E)-N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide; (E)-N-hydroxy-3-(3-(N-phenylsulfamoyl)phenyl)acrylamide; (E)-N-hydroxy-3-[3-(phenylsulfamoyl)phenyl]prop-2-enamide; 414864-00-9; 866323-14-0; CHEBI:61076; F4H96P17NZ; N-HYDROXY-3-(3-PHENYLSULFAMOYLPHENYL)ACRYLAMIDE; N-HYDROXY-3-[3-[(PHENYLAMINO)SULFONYL]PHENYL]-2-PROPENAMIDE; N-Hydroxy-3-(3-phenylsulphamoylphenyl)acrylamide; NSC726630; UNII-F4H96P17NZ
Indication Anaplastic large cell lymphoma [ICD11: 2A90] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 318.3 Topological Polar Surface Area 104
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
6918638
PubChem SID
12015640 ; 14899204 ; 17195013 ; 43530003 ; 48426953 ; 56374291 ; 57371991 ; 71821512 ; 79324295 ; 87226498 ; 87352001 ; 96025553 ; 99436973 ; 103572083 ; 104222411 ; 114788279 ; 124756987 ; 125163792 ; 126639499 ; 126671543 ; 126731246 ; 131480674 ; 134339486 ; 134964364 ; 135195315 ; 135727448 ; 136367285 ; 136368059 ; 136920289 ; 137008794 ; 142692247 ; 143496443 ; 144115689 ; 152234942 ; 152258138 ; 152344183 ; 160646977 ; 162011830 ; 162037424 ; 164041886 ; 164193975 ; 164202300 ; 170497642 ; 174529326 ; 175608161 ; 177748389 ; 179236375 ; 186022467 ; 187051798 ; 188899535
ChEBI ID
CHEBI:61076
CAS Number
866323-14-0
TTD Drug ID
D0XT6W
Formula
C15H14N2O4S
Canonical SMILES
C1=CC=C(C=C1)NS(=O)(=O)C2=CC=CC(=C2)C=CC(=O)NO
InChI
1S/C15H14N2O4S/c18-15(16-19)10-9-12-5-4-8-14(11-12)22(20,21)17-13-6-2-1-3-7-13/h1-11,17,19H,(H,16,18)/b10-9+
InChIKey
NCNRHFGMJRPRSK-MDZDMXLPSA-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
3-ASBA (3-Anilino-Sulfonyl Benzene Carboxylic Acid) DM005655
22492441
Unclear 1 [2]
Belinostat Acid DM005656
759339
Unclear 1 [2]
Belinostat Amide DM005654
69620795
Unclear 1 [2]
Belinostat glucuronide DM005653
91800105
Conjugation - Glucuronidation 1 [3] , [5]
Methylated Belinostat DM005657
72376230
Unclear 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006030 Belinostat Belinostat glucuronide Conjugation - Glucuronidation Unclear [3], [5]
MR006031 Belinostat Belinostat Amide Unclear CYP3A4 ... [2]
MR006032 Belinostat 3-ASBA (3-Anilino-Sulfonyl Benzene Carboxylic Acid) Unclear Unclear [2]
MR006033 Belinostat Belinostat Acid Unclear CYP3A4 ... [2]
MR006034 Belinostat Methylated Belinostat Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3] , [5]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[3] , [5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[3] , [5]
⏷ Show the Full List of 7  DME(s)
References
1 FDA approval: belinostat for the treatment of patients with relapsed or refractory peripheral T-cell lymphoma. Clin Cancer Res. 2015 Jun 15;21(12):2666-70.
2 Pharmacokinetics, metabolism, and excretion of (14)C-labeled belinostat in patients with recurrent or progressive malignancies
3 Glucuronidation by UGT1A1 is the dominant pathway of the metabolic disposition of belinostat in liver cancer patients. PLoS One. 2013;8(1):e54522.
4 Effects of UGT1A1 genotype on the pharmacokinetics, pharmacodynamics, and toxicities of belinostat administered by 48-hour continuous infusion in patients with cancer. J Clin Pharmacol. 2016 Apr;56(4):461-73.
5 In vitro characterization of belinostat glucuronidation: demonstration of both UGT1A1 and UGT2B7 as the main contributing isozymes

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