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

General Information of Drug (ID: DR3198)
Drug Name
S-297995
Synonyms
NALDEMEDINE; UNII-03KSI6WLXH; 03KSI6WLXH; S-297,995; 916072-89-4; Naldemedine [USAN:INN]; Naldemedine (USAN/INN); S 297995; SCHEMBL9880572; GTPL9150; CHEMBL2105755; AKOS032945757; DB11691; Morphinan-7-carboxamide, 17-(cyclopropylmethyl)-6,7-didehydro-4,5-epoxy-3,6,14- trihydroxy-N-(1-methyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)ethyl)-,(5alpha)-; J3.573.009E; D10188
Indication Opiate dependence [ICD11: 6C43] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 570.6 Topological Polar Surface Area 141
Heavy Atom Count 42 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
54732242
CAS Number
916072-89-4
TTD Drug ID
D0Q3PD
Formula
C32H34N4O6
Canonical SMILES
CC(C)(C1=NC(=NO1)C2=CC=CC=C2)NC(=O)C3=C([C@H]4[C@@]56CCN([C@@H]([C@@]5(C3)O)CC7=C6C(=C(C=C7)O)O4)CC8CC8)O
InChI
InChI=1S/C32H34N4O6/c1-30(2,29-33-27(35-42-29)18-6-4-3-5-7-18)34-28(39)20-15-32(40)22-14-19-10-11-21(37)25-23(19)31(32,26(41-25)24(20)38)12-13-36(22)16-17-8-9-17/h3-7,10-11,17,22,26,37-38,40H,8-9,12-16H2,1-2H3,(H,34,39)/t22-,26+,31+,32-/m1/s1
InChIKey
AXQACEQYCPKDMV-RZAWKFBISA-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
Benzamidine DM014853
2332
Multi-steps Reaction - Reduction; Hydrolysis 1 [4]
Naidemedine-(7R)-7-hydroxide DM019060 N. A. Oxidation - Oxidation 1 [4]
Naidemedine-(7S)-7-hydroxide DM019061 N. A. Oxidation - Oxidation 1 [4]
Naidemedine-3-G DM019062 N. A. Conjugation - Glucuronide conjugation 1 [4]
Naldemedine carboxylic acid DM016824
156596433
Hydrolysis - Hydrolysis 1 [4]
Nor-naldemedine DM016794
155804781
Oxidation - N-dealkylation 1 [4]
GDC-0152 M24 DM014814
464
Multi-steps Reaction - Oxidation,Glycine conjugation 2 [4]
MS416 DM019059 N. A. Multi-steps Reaction - Reduction; Hydrolysis 2 [4]
MS416 DM019059 N. A. Oxidation - N-dealkylation 2 [4]
MS486 DM019057 N. A. Oxidation - Oxidation 2 [4]
MS502 DM019058 N. A. Oxidation - Oxidation 3 [4]
⏷ 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
MR011485 S-297995 Naldemedine carboxylic acid Hydrolysis - Hydrolysis Unclear [4]
MR011489 S-297995 Nor-naldemedine Oxidation - N-dealkylation CYP3A [4]
MR011491 S-297995 Benzamidine Multi-steps Reaction - Reduction; Hydrolysis Unclear [4]
MR011493 S-297995 Naidemedine-(7R)-7-hydroxide Oxidation - Oxidation Unclear [4]
MR011494 S-297995 Naidemedine-(7S)-7-hydroxide Oxidation - Oxidation Unclear [4]
MR011495 S-297995 Naidemedine-3-G Conjugation - Glucuronide conjugation UGT1A3 [4]
MR011492 Benzamidine MS179 Multi-steps Reaction - Oxidation,Glycine conjugation Unclear [4]
MR011486 Naldemedine carboxylic acid MS486 Oxidation - Oxidation Unclear [4]
MR011488 Naldemedine carboxylic acid MS416 Oxidation - N-dealkylation Unclear [4]
MR011490 Nor-naldemedine MS416 Multi-steps Reaction - Reduction; Hydrolysis Unclear [4]
MR011487 MS486 MS502 Oxidation - Oxidation Unclear [4]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
References
1 Clinical pipeline report, company report or official report of Shionogi (2011).
2 Clinical Drug-Drug Interaction Studies to Evaluate the Effects of a P-Glycoprotein Inhibitor, CYP3A Inhibitors, and a CYP3A Inducer on the Pharmacokinetics of Naldemedine in Healthy Subjects
3 Naldemedine: First Global Approval
4 Absorption, distribution, metabolism, and excretion of radiolabeled naldemedine in healthy subjects

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