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

General Information of Drug (ID: DR1430)
Drug Name
Ritonavir
Synonyms
Ritonavir, 98%; ABBOTT-84538; ABT 538; ABT-538; Abbott 84538; CHEBI:45409; DRG-0244; Norvir; Norvir Softgel; O3J8G9O825; ritonavir; 155213-67-5; 5-Thiazolylmethyl ((alphaS)-alpha-((1S,3S-1-hydroxy-3-((2S)-2-(3-((2-isopropyl-4-thiazolyl)methyl)-3-methylureido)-3-methylbutyramido)-4-phenylbutyl)phenethyl)carbamate; A-84538; DSSTox_CID_28553; DSSTox_GSID_48627; DSSTox_RID_82825; HSDB 7160; MFCD00927142; NCGC00159462-02; NCGC00183130-01; NSC693184; RTV; UNII-O3J8G9O825
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 720.9 Topological Polar Surface Area 202
Heavy Atom Count 50 Rotatable Bond Count 18
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
392622
PubChem SID
9449 ; 523930 ; 583815 ; 612199 ; 822215 ; 827183 ; 855141 ; 7847493 ; 7890279 ; 7980525 ; 8030461 ; 10279496 ; 11528746 ; 12014859 ; 14766505 ; 14790837 ; 17422094 ; 26719904 ; 29215414 ; 46386817 ; 46392172 ; 46393138 ; 46505050 ; 49681649 ; 53789763 ; 57402349 ; 71825024 ; 79712259 ; 81092847 ; 92308258 ; 92711419 ; 93166545 ; 93167041 ; 99436927 ; 103244854 ; 104178993 ; 104616751 ; 104829353 ; 117877983 ; 118048821 ; 124658994 ; 124757062 ; 124801360 ; 124876828 ; 124892213 ; 124894323 ; 125163866 ; 125333191 ; 126592976 ; 126630875
ChEBI ID
CHEBI:45409
CAS Number
155213-67-5
TTD Drug ID
D0ZU9R
Formula
C37H48N6O5S2
Canonical SMILES
CC(C)C1=NC(=CS1)CN(C)C(=O)NC(C(C)C)C(=O)NC(CC2=CC=CC=C2)CC(C(CC3=CC=CC=C3)NC(=O)OCC4=CN=CS4)O
InChI
1S/C37H48N6O5S2/c1-24(2)33(42-36(46)43(5)20-29-22-49-35(40-29)25(3)4)34(45)39-28(16-26-12-8-6-9-13-26)18-32(44)31(17-27-14-10-7-11-15-27)41-37(47)48-21-30-19-38-23-50-30/h6-15,19,22-25,28,31-33,44H,16-18,20-21H2,1-5H3,(H,39,45)(H,41,47)(H,42,46)/t28-,31-,32-,33-/m0/s1
InChIKey
NCDNCNXCDXHOMX-XGKFQTDJSA-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
N-Desmethylritonavir DM016085
44334979
Other reaction - Hydoxylation 1 [7]
N-Desmethylritonavir DM016085
44334979
Oxidation - N-demethylation 1 [7]
Ritonavir metabolite M1 DM015762
11467322
Unclear - Unclear 1 [7]
Ritonavir metabolite M11 DM016245
66832582
Unclear - Unclear 1 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009550 Ritonavir N-Desmethylritonavir Oxidation - N-demethylation CYP3A5 ... [7]
MR009551 Ritonavir Ritonavir metabolite M1 Unclear - Unclear CYP3A5 ... [7]
MR009552 Ritonavir Ritonavir metabolite M11 Unclear - Unclear CYP3A5 ... [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [6]
⏷ Show the Full List of 17  DME(s)
References
1 Ritonavir was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Evaluation of CYP2B6 induction and prediction of clinical drug-drug interactions: considerations from the IQ consortium induction working group-an industry perspective. Drug Metab Dispos. 2016 Oct;44(10):1720-30.
3 Reversible coma caused by risperidone-ritonavir interaction. Clin Neuropharmacol. 2002 Sep-Oct;25(5):251-3.
4 Effect of extended exposure to grapefruit juice on cytochrome P450 3A activity in humans: comparison with ritonavir. Clin Pharmacol Ther. 2006 Mar;79(3):243-54.
5 Drug Interactions Flockhart Table
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.

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