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

General Information of Drug (ID: DR0963)
Drug Name
Lisdexamfetamine
Synonyms
Lisdexamfetamine; Lisdexamfetamine (INN); Lisdexamfetamine [INN]; SCHEMBL158949; L-lysine-d-amphetamine; LS-187377; Vyvanse; ZINC11680943; (2S)-2,6-Diamino-N-((1S)-1-methyl-2-phenylethyl)hexanamide; (2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide; 608137-32-2; CHEBI:135925; CHEMBL1201222; D08130; DB01255; DTXSID00209652; GTPL7213; H645GUL8KJ; HSDB 8277; NRP104; UNII-H645GUL8KJ
Indication Attention deficit hyperactivity disorder [ICD11: 6A05] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 263.38 Topological Polar Surface Area 81.1
Heavy Atom Count 19 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
11597698
PubChem SID
16843305 ; 23710324 ; 42764532 ; 46505358 ; 50070913 ; 78572726 ; 96024820 ; 126651840 ; 135195272 ; 136939966 ; 137001224 ; 137228331 ; 140917534 ; 160964587 ; 175265708 ; 178103788 ; 179150769 ; 224607397 ; 226522546 ; 244397481
ChEBI ID
CHEBI:135925
CAS Number
608137-32-2
TTD Drug ID
D00DEF
Formula
C15H25N3O
Canonical SMILES
CC(CC1=CC=CC=C1)NC(=O)C(CCCCN)N
InChI
1S/C15H25N3O/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19)/t12-,14-/m0/s1
InChIKey
VOBHXZCDAVEXEY-JSGCOSHPSA-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
D-amphetamine DM006407
5826
Oxidation - Hydrolyzationn 1 [2]
L-Lysine DM006411
5962
Oxidation - Hydrolyzationn 1 [2]
Alpha-hydroxy-amphetamine DM006408 N. A. Oxidation - Oxidationn 2 [2]
Fenethylline Metabolite M-5( p-hydroxy-AP) DM000822
3651
Oxidation - Oxidationn 2 [2]
Norephedrine DM001363
26934
Oxidation - Oxidationn 2 [2]
(-)-4-Hydroxynorephedrin DM006410
6931143
Oxidation - Oxidationn 3 [2]
Metamfetamine Metabolite M5 DM001359
7678
Oxidation - Deamination 3 [2]
Midostaurin Metabolite P6 DM001360
243
Unclear 4 [2]
Midostaurin Metabolite P6B DM001361
464
Unclear 4 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006881 Lisdexamfetamine D-amphetamine Oxidation - Hydrolyzationn Unclear [2]
MR006890 Lisdexamfetamine L-Lysine Oxidation - Hydrolyzationn Unclear [2]
MR006882 D-amphetamine Alpha-hydroxy-amphetamine Oxidation - Oxidationn Unclear [2]
MR006886 D-amphetamine 4-(2-Aminopropyl)phenol Oxidation - Oxidationn Unclear [2]
MR006888 D-amphetamine Norephedrine Oxidation - Oxidationn CYP2D6 [2]
MR006887 4-(2-Aminopropyl)phenol (-)-4-Hydroxynorephedrin Oxidation - Oxidationn Unclear [2]
MR006883 Alpha-hydroxy-amphetamine Phenylacetone Oxidation - Deamination Unclear [2]
MR006889 Norephedrine (-)-4-Hydroxynorephedrin Oxidation - Oxidationn Unclear [2]
MR006884 Phenylacetone Benzoic Acid Unclear Unclear [2]
MR006885 Phenylacetone Hippuric acid Unclear Unclear [2]
⏷ 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
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
References
1 Lisdexamfetamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Preclinical pharmacokinetics, pharmacology and toxicology of lisdexamfetamine: a novel d-amphetamine pro-drug. Neuropharmacology. 2014 Dec;87:41-50.

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