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

General Information of Drug (ID: DR5624)
Drug Name
Orlistat
Synonyms
orlistat; 96829-58-2; Tetrahydrolipstatin; Xenical; Alli; Orlipastat; (-)-Tetrahydrolipstatin; Orlipastatum; Orlipastatum [INN-Latin]; THLP; Ro-18-0647; UNII-95M8R751W8; C29H53NO5; Ro 18-0647/002; N-Formyl-L-leucine (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester; (2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl (2S)-2-formamido-4-methylpentanoate; Orlistat (Alli, Xenical); MLS002207022; [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] (2S)-2-formamido-4-methylpentanoate; CHEMBL175247; Alli; GlaxoSmithKline brand of orlistat; Roche brand of orlistat; Alli (TN); Hoffmann-La Roche brand of orlistat; KS-1183; Orlistat [USAN:INN]; R-212; Xenical (TN); Orlistat (USAN/INN); Ro 18-0647/008; Alli, Xenical, Tetrahydrolipstatin, Orlistat; N-Formyl-L-leucine, ester with (3S,4S)-3-hexyl-4-((2S)-2-hydroxytridecyl)-2-oxetanone; L-Leucine, N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester; L-Leucine,N-formyl-, (1S)-1-(((2S,3S)-3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl ester; 1-((3-hexyl-4-oxo-2-oxetanyl)methyl)dodecyl-2-formamido-4-methylvalerate; TETRAHYDROLIPSTATIN
Indication Obesity [ICD11: 5B80-5B81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 495.7 Topological Polar Surface Area 81.7
Heavy Atom Count 35 Rotatable Bond Count 23
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3034010
ChEBI ID
CHEBI:94686
CAS Number
96829-58-2
TTD Drug ID
D0T9TJ
Formula
C29H53NO5
Canonical SMILES
CCCCCCCCCCC[C@@H](C[C@H]1[C@@H](C(=O)O1)CCCCCC)OC(=O)[C@H](CC(C)C)NC=O
InChI
InChI=1S/C29H53NO5/c1-5-7-9-11-12-13-14-15-16-18-24(34-29(33)26(30-22-31)20-23(3)4)21-27-25(28(32)35-27)19-17-10-8-6-2/h22-27H,5-21H2,1-4H3,(H,30,31)/t24-,25-,26-,27-/m0/s1
InChIKey
AHLBNYSZXLDEJQ-FWEHEUNISA-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
Orlistat Metabolite M1 DM015875
14607536
Unclear - Unclear 1 [5]
Orlistat Metabolite M3 DM015876
14607537
Unclear - Unclear 2 [5]
Orlistat Metabolite M7 DM016506
102506559
Unclear - Unclear 3 [5]
Orlistat Metabolite M9 DM016368
85712366
Unclear - Unclear 4 [5]
Ro 61-0593 DM016505
102506558
Unclear - Unclear 5 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010573 Orlistat Orlistat Metabolite M1 Unclear - Unclear Unclear [5]
MR010574 Orlistat Metabolite M1 Orlistat Metabolite M3 Unclear - Unclear Unclear [5]
MR010575 Orlistat Metabolite M3 Orlistat Metabolite M7 Unclear - Unclear Unclear [5]
MR010576 Orlistat Metabolite M7 Orlistat Metabolite M9 Unclear - Unclear Unclear [5]
MR010577 Orlistat Metabolite M9 Ro 61-0593 Unclear - Unclear Unclear [5]
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]
Cytosolic phospholipase A2 (PLA2G4A) DME0225 Homo sapiens
PA24A_HUMAN
3.1.1.4
[3]
Fatty acid synthase (FASN) DMEN219 Homo sapiens
A0A0U1RQF0_HUMAN
1.1.1.100
[4]
References
1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 DrugBank(Pharmacology-Metabolism):Orlistat
3 The effect of orlistat and fenofibrate, alone or in combination, on small dense LDL and lipoprotein-associated phospholipase A2 in obese patients with metabolic syndrome
4 U. S. FDA Label -Orlistat
5 Metabolic profiles of minimally absorbed orlistat in obese/overweight volunteers

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