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

General Information of Drug (ID: DR0420)
Drug Name
Darunavir
Synonyms
Darunavir; Darunavirum; Darunavirum [INN-Latin]; MFCD09260006; NCGC00168773-01; TMC 114; TMC-114; TMC114; UIC-94017; UNII-YO603Y8113; YO603Y8113; (3R,3AS,6AR)-HEXAHYDROFURO[2,3-B]FURAN-3-YL(1S,2R)-3-[[(4-AMINOPHENYL)SULFONYL](ISOBUTYL)AMINO]-1-BENZYL-2-HYDROXYPROPYLCARBAMATE; (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate; 206361-99-1; AIDS073035; CHEBI:367163; CHEMBL1323
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 547.7 Topological Polar Surface Area 149
Heavy Atom Count 38 Rotatable Bond Count 12
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
213039
PubChem SID
628316 ; 7884953 ; 9371109 ; 10322685 ; 10322696 ; 11108879 ; 12015589 ; 14719987 ; 14719990 ; 14720157 ; 14788134 ; 17397753 ; 30417278 ; 46394098 ; 46394099 ; 46394100 ; 46394252 ; 46394253 ; 46394275 ; 46394276 ; 46506908 ; 49661683 ; 49743126 ; 49743141 ; 49743143 ; 50070565 ; 50071308 ; 50074527 ; 50113275 ; 50333303 ; 53777066 ; 57399654 ; 85098698 ; 85177032 ; 85177058 ; 85756739 ; 85756740 ; 87351130 ; 87557585 ; 87557699 ; 87557709 ; 87557710 ; 99226867 ; 99226870 ; 99226871 ; 104223585 ; 104234207 ; 113453152 ; 115001517 ; 117695824
ChEBI ID
CHEBI:367163
CAS Number
206361-99-1
TTD Drug ID
D03IGH
Formula
C27H37N3O7S
Canonical SMILES
CC(C)CN(CC(C(CC1=CC=CC=C1)NC(=O)OC2COC3C2CCO3)O)S(=O)(=O)C4=CC=C(C=C4)N
InChI
1S/C27H37N3O7S/c1-18(2)15-30(38(33,34)21-10-8-20(28)9-11-21)16-24(31)23(14-19-6-4-3-5-7-19)29-27(32)37-25-17-36-26-22(25)12-13-35-26/h3-11,18,22-26,31H,12-17,28H2,1-2H3,(H,29,32)/t22-,23-,24+,25-,26+/m0/s1
InChIKey
CJBJHOAVZSMMDJ-HEXNFIEUSA-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
Darunavir metabolite MB DM001909
9888792
Unclear 1 [3]
Darunavir metabolite MC DM001910
8479
Unclear 1 [3]
Darunavir metabolite MD DM001911
5362440
Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000741 Darunavir Darunavir metabolite MB Unclear CYP3A4 [3]
MR000742 Darunavir Darunavir metabolite MC Unclear Unclear [3]
MR000743 Darunavir Darunavir metabolite MD Unclear Unclear [3]
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]
References
1 Darunavir Ethanolate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Drug interactions with new and investigational antiretrovirals. Clin Pharmacokinet. 2009;48(4):211-41.
3 LC-Q-TOF-MS/MS determination of darunavir and its metabolites in rat serum and urine: application to pharmacokinetics J Pharm Biomed Anal. 2014 Jun;94:92-8. doi: 10.1016/j.jpba.2014.01.035.

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