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

General Information of Drug (ID: DR3036)
Drug Name
MK-499
Synonyms
MK-499; MK 499; L-706000; L 706000; L-706,000; SCHEMBL4706649; CHEMBL477015; GTPL2607; BDBM24064; MK499; [35S]-MK499; N-[[3,4-Dihydro-4beta-hydroxy-1'-[[(R)-6-cyano-1,2,3,4-tetrahydronaphthalen]-2-yl]spiro[2H-1-benzopyran-2,4'-piperidin]]-6-yl]methanesulfonamide; N-[(4R)-1''-[(2R)-6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl]-3,4-dihydrospiro[1-benzopyran-2,4''-piperidine]-4-ol]methanesulfonamide
Indication Cardiac arrhythmias [ICD11: BC9Z] Discontinued in Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 467.6 Topological Polar Surface Area 111
Heavy Atom Count 33 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
9934294
CAS Number
150481-98-4
TTD Drug ID
D02NGR
Formula
C25H29N3O4S
Canonical SMILES
CS(=O)(=O)NC1=CC2=C(C=C1)OC3(CCN(CC3)[C@@H]4CCC5=C(C4)C=CC(=C5)C#N)C[C@H]2O
InChI
InChI=1S/C25H29N3O4S/c1-33(30,31)27-20-5-7-24-22(14-20)23(29)15-25(32-24)8-10-28(11-9-25)21-6-4-18-12-17(16-26)2-3-19(18)13-21/h2-3,5,7,12,14,21,23,27,29H,4,6,8-11,13,15H2,1H3/t21-,23-/m1/s1
InChIKey
NIYGLRKUBPNXQS-FYYLOGMGSA-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
Glutathione DM003449
124886
Unclear - Unclear 1 [2]
MK-499 Metabolite M1 DM018332 N. A. Unclear - N-substitution 1 [2]
MK-499 Metabolite M2 DM018333 N. A. Oxidation - 4 hydroxylation 1 [2]
MK-499 Metabolite M3 DM018334 N. A. Unclear - Unclear 1 [2]
MK-499 Metabolite M4 DM018335 N. A. Oxidation - 4 hydroxylation 1 [2]
MK-499 Metabolite M7 DM018337 N. A. Conjugation - Glucuronidation 1 [2]
N-acetyl-1-cysteine DM018336 N. A. Unclear - Unclear 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010317 MK-499 MK-499 Metabolite M1 Unclear - N-substitution Unclear [2]
MR010318 MK-499 MK-499 Metabolite M2 Oxidation - 4 hydroxylation Unclear [2]
MR010319 MK-499 MK-499 Metabolite M3 Unclear - Unclear Unclear [2]
MR010320 MK-499 MK-499 Metabolite M4 Oxidation - 4 hydroxylation Unclear [2]
MR010321 MK-499 Glutathione Unclear - Unclear Unclear [2]
MR010322 MK-499 N-acetyl-1-cysteine Unclear - Unclear Unclear [2]
MR010323 MK-499 MK-499 Metabolite M7 Conjugation - Glucuronidation Unclear [2]
⏷ Show the Full List of 7 MR(s)
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: 2607).
2 Metabolism of MK-499, a class III antiarrhythmic agent, in rats and dogs

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