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

General Information of Drug (ID: DR1601)
Drug Name
Tipranavir
Synonyms
Tipranavir; U-140690; Aptivus; PNU 140690; PNU-140690; ZZT404XD09; 174484-41-4; 3'-((1R)-1-((6R)-5,6-Dihydro-4-hydroxy-2-oxo-6-phenethyl-6-propyl-2H-pyran-3-yl)propyl)-5-(trifluoromethyl)-2-pyridinesulfonanilide; CHEBI:63628; N-(3-{(1R)-1-[(6R)-4-HYDROXY-2-OXO-6-PHENETHYL-6-PROPYL-5,6-DIHYDRO-2H-PYRAN-3-YL]PROPYL}PHENYL)-5-(TRIFLUOROMETHYL)-2-PYRIDINESULFONAMIDE; N-[3-[(1R)-1-[(2R)-6-hydroxy-4-oxo-2-phenethyl-2-propyl-3H-pyran-5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide; TPV; UNII-ZZT404XD09
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 602.7 Topological Polar Surface Area 114
Heavy Atom Count 42 Rotatable Bond Count 11
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 10
Cross-matching ID
PubChem CID
54682461
ChEBI ID
CHEBI:63628
CAS Number
174484-41-4
TTD Drug ID
D0EV6T
Formula
C31H33F3N2O5S
Canonical SMILES
CCCC1(CC(=C(C(=O)O1)C(CC)C2=CC(=CC=C2)NS(=O)(=O)C3=NC=C(C=C3)C(F)(F)F)O)CCC4=CC=CC=C4
InChI
1S/C31H33F3N2O5S/c1-3-16-30(17-15-21-9-6-5-7-10-21)19-26(37)28(29(38)41-30)25(4-2)22-11-8-12-24(18-22)36-42(39,40)27-14-13-23(20-35-27)31(32,33)34/h5-14,18,20,25,36-37H,3-4,15-17,19H2,1-2H3/t25-,30-/m1/s1
InChIKey
SUJUHGSWHZTSEU-FYBSXPHGSA-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
Tipranavir Metabolite DM004664 N. A. Oxidation - Dihydroxylation 1 [3]
Tipranavir Metabolite DM004663 N. A. Oxidation - Dehydrogenation 1 [3]
Tipranavir Metabolite DM004662 N. A. Oxidation - Dehydrogenation 1 [3]
Tipranavir Metabolite DM004661 N. A. Oxidation - Dehydrogenation 1 [3]
Tipranavir Metabolite DM004660 N. A. Oxidation - Depropylation 1 [3]
Tipranavir Metabolite DM004659 N. A. Oxidation - Monohydroxylation 1 [3]
Tipranavir Metabolite DM004658 N. A. Oxidation - Monohydroxylation 1 [3]
Tipranavir Metabolite DM004657 N. A. Oxidation - Monohydroxylation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005002 Tipranavir Tipranavir Metabolite Oxidation - Monohydroxylation CYP3A4 [3]
MR005003 Tipranavir Tipranavir Metabolite Oxidation - Monohydroxylation CYP3A4 ... [3]
MR005004 Tipranavir Tipranavir Metabolite Oxidation - Monohydroxylation CYP3A4 [3]
MR005005 Tipranavir Tipranavir Metabolite Oxidation - Depropylation CYP3A4 [3]
MR005006 Tipranavir Tipranavir Metabolite Oxidation - Dehydrogenation CYP3A4 [3]
MR005007 Tipranavir Tipranavir Metabolite Oxidation - Dehydrogenation Unclear [3]
MR005008 Tipranavir Tipranavir Metabolite Oxidation - Dehydrogenation Unclear [3]
MR005009 Tipranavir Tipranavir Metabolite Oxidation - Dihydroxylation Unclear [3]
⏷ Show the Full List of 8 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]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Tipranavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A phenotype-genotype approach to predicting CYP450 and P-glycoprotein drug interactions with the mixed inhibitor/inducer tipranavir/ritonavir. Clin Pharmacol Ther. 2010 Jun;87(6):735-42.
3 Metabolism-mediated drug interactions associated with ritonavir-boosted tipranavir in mice. Drug Metab Dispos. 2010 May;38(5):871-8.

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