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

General Information of Drug (ID: DR1832)
Drug Name
SB-939
Synonyms
GPO2JN4UON; Pracinostat; Pracinostat (SB939); Pracinostat [INN]; SB 939; SB-939; (2E)-3-(2-Butyl-1-[2-(diethylamino)ethyl]-1h-1,3-benzodiazol-5-yl)-n-hydroxyprop-2-enamide; (E)-3-(2-butyl-1-(2-(diethylamino)ethyl)-1H-benzo[d]imidazol-5-yl)-N-hydroxyacrylamide; 2-Propenamide, 3-(2-butyl-1-(2-(diethylamino)ethyl)-1H-benzimidazol-5-yl)-N-hydroxy-, (2E)-; 2-Propenamide, 3-[2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxy-, (2E)-; 929016-96-6; CHEMBL1851943; SB939; UNII-GPO2JN4UON
Indication Acute myeloid leukaemia [ICD11: 2A60] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 358.5 Topological Polar Surface Area 70.4
Heavy Atom Count 26 Rotatable Bond Count 10
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
49855250
PubChem SID
104253187 ; 121142796 ; 124757307 ; 125164111 ; 131480903 ; 134964553 ; 135264258 ; 136340267 ; 136359913 ; 136367450 ; 136920413 ; 137055167 ; 137390461 ; 140705810 ; 152258538 ; 160647372 ; 162011419 ; 162037638 ; 162202712 ; 163668154 ; 164193974 ; 172659608 ; 174520548 ; 174531534 ; 185973726 ; 188899586 ; 198945398 ; 202535654 ; 223366695 ; 223388553 ; 223705232 ; 227106278 ; 251963214 ; 252110018 ; 252160441 ; 252166577 ; 252216278 ; 252451771
ChEBI ID
CHEBI:95071
CAS Number
929016-96-6
TTD Drug ID
D0L2UQ
Formula
C20H30N4O2
Canonical SMILES
CCCCC1=NC2=C(N1CCN(CC)CC)C=CC(=C2)C=CC(=O)NO
InChI
1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
InChIKey
JHDKZFFAIZKUCU-ZRDIBKRKSA-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
SB-939 Metabolite M1 DM005981
16068493
Oxidation - N-deethylation 1 [2]
SB-939 Metabolite M2/M3/M4 DM005983 N. A. Oxidation - Oxidationn 1 [2]
SB-939 Metabolite M6 DM005986
154572837
Oxidation - Bis-N-deethylation 1 [2]
SB-939 Metabolite M7 DM005985 N. A. Oxidation - Oxidationn 1 [2]
SB-939 Metabolite M8 DM005987 N. A. Unclear 1 [2]
SB-939 Metabolite M5 DM005982 N. A. Oxidation - N-deethylation 2 [2]
SB-939 Metabolite M5 DM005982 N. A. Oxidation - Oxidationn 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006440 SB-939 SB-939 Metabolite M1 Oxidation - N-deethylation CYP1A2 ... [2]
MR006442 SB-939 SB-939 Metabolite M2/M3/M4 Oxidation - Oxidationn Unclear [2]
MR006444 SB-939 SB-939 Metabolite M7 Oxidation - Oxidationn Unclear [2]
MR006445 SB-939 SB-939 Metabolite M6 Oxidation - Bis-N-deethylation Unclear [2]
MR006446 SB-939 SB-939 Metabolite M8 Unclear Unclear [2]
MR006441 SB-939 Metabolite M1 SB-939 Metabolite M5 Oxidation - Oxidationn Unclear [2]
MR006443 SB-939 Metabolite M2/M3/M4 SB-939 Metabolite M5 Oxidation - N-deethylation Unclear [2]
⏷ Show the Full List of 7 MR(s)
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]
References
1 ClinicalTrials.gov (NCT03151408) An Efficacy and Safety Study Of Pracinostat In Combination With Azacitidine In Adults With Acute Myeloid Leukemia.
2 Preclinical metabolism and disposition of SB939 (Pracinostat), an orally active histone deacetylase inhibitor, and prediction of human pharmacokinetics. Drug Metab Dispos. 2011 Dec;39(12):2219-32.

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