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

General Information of Drug (ID: DR1718)
Drug Name
WIN 55212-2
Synonyms
WIN 55,212-2; WIN 55212-2; WIN-55212; WIN55212-2; Win 55,212; Win-55212-2; (2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl)methanone; (2,3-Dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl)methanone monomethanesulfonate; (r)-(+)-[2,3-dihydro-5-methyl-3-(4-morpholinylmethyl)pyrrolo[1,2,3-de]-1,4-benzoxazin-6-yl]-1-naphthalenylmethanone; 131543-22-1; 5H31GI9502; CHEBI:73295; CHEMBL188; UNII-5H31GI9502
Indication Anaesthesia [ICD11: 8E22] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 426.5 Topological Polar Surface Area 43.7
Heavy Atom Count 32 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5311501
PubChem SID
7980892 ; 11056544 ; 12014569 ; 14782868 ; 14929727 ; 26754855 ; 26754856 ; 39341166 ; 47647616 ; 48395014 ; 49681172 ; 49689353 ; 50110805 ; 50110806 ; 57359506 ; 77916044 ; 85787707 ; 90341664 ; 92309954 ; 99300867 ; 103513296 ; 124750377 ; 124881896 ; 124881897 ; 124881898 ; 124881899 ; 124881900 ; 124881901 ; 124881902 ; 128100013 ; 134342487 ; 135651326 ; 142472540 ; 162169305 ; 164766158 ; 179335180 ; 223591298 ; 226490429 ; 249967380 ; 252319849
ChEBI ID
CHEBI:73295
CAS Number
131543-22-1
TTD Drug ID
D0J7RW
Formula
C27H26N2O3
Canonical SMILES
CC1=C(C2=C3N1C(COC3=CC=C2)CN4CCOCC4)C(=O)C5=CC=CC6=CC=CC=C65
InChI
1S/C27H26N2O3/c1-18-25(27(30)22-9-4-7-19-6-2-3-8-21(19)22)23-10-5-11-24-26(23)29(18)20(17-32-24)16-28-12-14-31-15-13-28/h2-11,20H,12-17H2,1H3/t20-/m1/s1
InChIKey
HQVHOQAKMCMIIM-HXUWFJFHSA-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
WIN 55212-2 Metabolite M1a DM004129 N. A. Oxidation - Hydrolyzationn 1 [4]
WIN 55212-2 Metabolite M1b DM004133 N. A. Oxidation - Oxidationn 1 [4]
WIN 55212-2 Metabolite M1c DM004118 N. A. Oxidation - Hydrolyzationn 1 [4]
WIN 55212-2 Metabolite M2a DM004128 N. A. Oxidation - Hydrolyzationn 2 [4]
WIN 55212-2 Metabolite M3a DM004132 N. A. Oxidation - Hydrolyzationn 2 [4]
WIN 55212-2 Metabolite M3b DM004135 N. A. Unclear 2 [4]
WIN 55212-2 Metabolite M4 DM004119 N. A. Oxidation - N-dealkylation; O-dealkylation 2 [4]
WIN 55212-2 Metabolite M5 DM004134 N. A. Oxidation - Hydrolyzationn 2 [4]
WIN 55212-2 Metabolite M8a DM004130 N. A. Oxidation - Hydrolyzationn 2 [3] , [4]
WIN 55212-2 Metabolite M2a DM004128 N. A. Oxidation - N-dealkylation; O-dealkylation 3 [4]
WIN 55212-2 Metabolite M2b DM004127 N. A. Oxidation - N-dealkylation; O-dealkylation 3 [4]
WIN 55212-2 Metabolite M3a DM004132 N. A. Oxidation - Hydrolyzationn 3 [4]
WIN 55212-2 Metabolite M6 DM004120 N. A. Oxidation - N-dealkylation 3 [4]
WIN 55212-2 Metabolite M8b DM004131 N. A. Unclear 3 [4]
WIN 55212-2 Metabolite M8b DM004131 N. A. Oxidation - Hydrolyzationn 3 [4]
WIN 55212-2 Metabolite M7a DM004121 N. A. Oxidation - Oxidationn deamination 4 [4]
WIN 55212-2 Metabolite M10 DM004126 N. A. Oxidation - Oxidationn 5 [4]
WIN 55212-2 Metabolite M7b DM004122 N. A. Oxidation - Oxidationn deamination 5 [4]
WIN 55212-2 Metabolite M9a DM004125 N. A. Oxidation - Hydrolyzationn 6 [4]
WIN 55212-2 Metabolite M9c DM004123 N. A. Oxidation - Hydrolyzationn 6 [4]
WIN 55212-2 Metabolite M9b DM004124 N. A. Oxidation - Dealkylation 7 [4]
⏷ Show the Full List of 21  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004508 WIN 55212-2 WIN 55212-2 Metabolite M1c Oxidation - Hydrolyzationn Unclear [4]
MR004519 WIN 55212-2 WIN 55212-2 Metabolite M1a Oxidation - Hydrolyzationn Unclear [4]
MR004523 WIN 55212-2 WIN 55212-2 Metabolite M1b Oxidation - Oxidationn Unclear [4]
MR004520 WIN 55212-2 Metabolite M1a WIN 55212-2 Metabolite M8a Oxidation - Hydrolyzationn EPHX1 [3], [4]
MR004526 WIN 55212-2 Metabolite M1a WIN 55212-2 Metabolite M3a Oxidation - Hydrolyzationn Unclear [4]
MR004527 WIN 55212-2 Metabolite M1a WIN 55212-2 Metabolite M3b Unclear Unclear [4]
MR004528 WIN 55212-2 Metabolite M1a WIN 55212-2 Metabolite M2a Oxidation - Hydrolyzationn Unclear [4]
MR004524 WIN 55212-2 Metabolite M1b WIN 55212-2 Metabolite M5 Oxidation - Hydrolyzationn Unclear [4]
MR004529 WIN 55212-2 Metabolite M1b WIN 55212-2 Metabolite M3b Unclear Unclear [4]
MR004509 WIN 55212-2 Metabolite M1c WIN 55212-2 Metabolite M4 Oxidation - N-dealkylation; O-dealkylation Unclear [4]
MR004530 WIN 55212-2 Metabolite M1c WIN 55212-2 Metabolite M2a Oxidation - Hydrolyzationn Unclear [4]
MR004510 WIN 55212-2 Metabolite M4 WIN 55212-2 Metabolite M6 Oxidation - N-dealkylation Unclear [4]
MR004517 WIN 55212-2 Metabolite M4 WIN 55212-2 Metabolite M2b Oxidation - N-dealkylation; O-dealkylation Unclear [4]
MR004518 WIN 55212-2 Metabolite M4 WIN 55212-2 Metabolite M2a Oxidation - N-dealkylation; O-dealkylation Unclear [4]
MR004525 WIN 55212-2 Metabolite M5 WIN 55212-2 Metabolite M8b Unclear Unclear [4]
MR004521 WIN 55212-2 Metabolite M8a WIN 55212-2 Metabolite M8b Oxidation - Hydrolyzationn Unclear [4]
MR004522 WIN 55212-2 Metabolite M8a WIN 55212-2 Metabolite M3a Oxidation - Hydrolyzationn Unclear [4]
MR004511 WIN 55212-2 Metabolite M6 WIN 55212-2 Metabolite M7a Oxidation - Oxidationn deamination Unclear [4]
MR004512 WIN 55212-2 Metabolite M7a WIN 55212-2 Metabolite M7b Oxidation - Oxidationn deamination Unclear [4]
MR004516 WIN 55212-2 Metabolite M7a WIN 55212-2 Metabolite M10 Oxidation - Oxidationn Unclear [4]
MR004513 WIN 55212-2 Metabolite M7b WIN 55212-2 Metabolite M9c Oxidation - Hydrolyzationn Unclear [4]
MR004515 WIN 55212-2 Metabolite M7b WIN 55212-2 Metabolite M9a Oxidation - Hydrolyzationn Unclear [4]
MR004514 WIN 55212-2 Metabolite M9c WIN 55212-2 Metabolite M9b Oxidation - Dealkylation Unclear [4]
⏷ Show the Full List of 23 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]
Epoxide hydrolase 1 (EPHX1) DME0623 Homo sapiens
HYEP_HUMAN
3.3.2.9
[3] , [4]
References
1 An analgesia circuit activated by cannabinoids. Nature. 1998 Sep 24;395(6700):381-3.
2 Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17.
3 In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo [1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist
4 Toxicokinetics of new psychoactive substances: plasma protein binding, metabolic stability, and human phase I metabolism of the synthetic cannabinoid WIN 55,212-2 studied using in vitro tools and LC-HR-MS/MS

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