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

General Information of Drug (ID: DR1869)
Drug Name
ARQ-501
Synonyms
ARQ 501; ARQ-501; Lapachone, beta-; SL 11001; beta-Lapachone; .beta.-Lapachone; 2,2-Dimethyl-3,4-dihydro-2H-benzo[h]chromene-5,6-dione; 2,2-dimethyl-3,4-dihydrobenzo[h]chromene-5,6-dione; 2H-Naphtho[1,2-b]pyran-5,6-dione, 3,4-dihydro-2,2-dimethyl-; 3,4-Dihydro-2,2-dimethyl-2H-naphtho(1,2-b)pyran-5,6-dione; 3,4-Dihydro-2,2-dimethyl-2H-naphtho[1,2-B]pyran-5,6-dione; 3,4-Dihydro-2,2-dimethyl-2H-naphthol[1,2-b]pyran-5,6-dione; 4707-32-8; 6N4FA2QQ6A; BRN 0181499; CHEBI:10429; NSC 26326; NSC 629749; UNII-6N4FA2QQ6A
Indication Leiomyosarcoma [ICD11: 2B58] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 242.27 Topological Polar Surface Area 43.4
Heavy Atom Count 18 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3885
PubChem SID
12553 ; 87198 ; 494711 ; 611544 ; 5669163 ; 8152448 ; 11111370 ; 11121371 ; 11121851 ; 11362440 ; 11365002 ; 11367564 ; 11370151 ; 11370152 ; 11373165 ; 11375726 ; 11414054 ; 15196477 ; 17405278 ; 24278512 ; 26753601 ; 29222999 ; 47365325 ; 47440387 ; 47589107 ; 47959891 ; 48110573 ; 48259373 ; 49996523 ; 50106535 ; 50106536 ; 50106537 ; 50106538 ; 53777823 ; 53788397 ; 57322036 ; 68530614 ; 79051855 ; 85087200 ; 85231108 ; 90340897 ; 91708861 ; 92304299 ; 92309722 ; 99300636 ; 99302154 ; 103178327 ; 103852913 ; 104304799 ; 117597465
ChEBI ID
CHEBI:10429
CAS Number
4707-32-8
TTD Drug ID
D0W0VD
Formula
C15H14O3
Canonical SMILES
CC1(CCC2=C(O1)C3=CC=CC=C3C(=O)C2=O)C
InChI
1S/C15H14O3/c1-15(2)8-7-11-13(17)12(16)9-5-3-4-6-10(9)14(11)18-15/h3-6H,7-8H2,1-2H3
InChIKey
QZPQTZZNNJUOLS-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
ARQ-501 M6 DM006733 N. A. Unclear 1 [3]
Catechol intermediate DM006725 N. A. Reduction - Reduction 1 [3]
Unclear DM009999 N. A. Hydrolysis - Hydrolysis 1 [3]
Unclear DM009999 N. A. Oxidation - Oxidationn 1 [3]
ARQ-501 M1 DM006726 N. A. Conjugation - Monoglucuronidation 2 [3]
ARQ-501 M2 DM006727 N. A. Conjugation - Monoglucuronidation 2 [3]
ARQ-501 M3-1 DM006731 N. A. Conjugation - Glucuronidation 2 [3]
ARQ-501 M3-2 DM006732 N. A. Conjugation - Glucuronidation 2 [3]
ARQ-501 M4-1 DM006729 N. A. Multi-steps Reaction - Reduction; glucuronidation 2 [3]
ARQ-501 M4-2 DM006730 N. A. Multi-steps Reaction - Reduction; glucuronidation 2 [3]
ARQ-501 M5 DM006728 N. A. Conjugation - Glucuronidation 2 [3]
⏷ 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
MR007262 ARQ-501 Catechol intermediate Reduction - Reduction NQO1 [3]
MR007266 ARQ-501 Unclear Oxidation - Oxidationn Unclear [3]
MR007271 ARQ-501 ARQ-501 M6 Unclear Unclear [3]
MR007263 Catechol intermediate ARQ-501 M1 Conjugation - Monoglucuronidation UGT2B7 [3]
MR007264 Catechol intermediate ARQ-501 M2 Conjugation - Monoglucuronidation UGT1A7 ... [3]
MR007265 Catechol intermediate ARQ-501 M5 Conjugation - Glucuronidation Unclear [3]
MR007267 Unclear ARQ-501 M4-1 Multi-steps Reaction - Reduction; glucuronidation NQO1 [3]
MR007268 Unclear ARQ-501 M4-2 Multi-steps Reaction - Reduction; glucuronidation NQO1 [3]
MR007269 Unclear ARQ-501 M3-1 Conjugation - Glucuronidation Unclear [3]
MR007270 Unclear ARQ-501 M3-2 Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 10 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Quinone reductase 1 (NQO1) DME0097 Homo sapiens
NQO1_HUMAN
1.6.5.2
[2]
References
1 Cancer therapy with beta-lapachone. Curr Cancer Drug Targets. 2002 Sep;2(3):227-42.
2 Beta-lapachone, a modulator of NAD metabolism, prevents health declines in aged mice. PLoS One. 2012;7(10):e47122.
3 Metabolic profile, enzyme kinetics, and reaction phenotyping of -lapachone metabolism in human liver and intestine in vitro

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