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

General Information of Drug (ID: DR1138)
Drug Name
Nelfinavir mesylate
Synonyms
Nelfin; Nelfinavir (Mesylate); Nelfinavir Mesylate [USAN]; Nelfinavir Methanesulfonate; Nelfinavir mesilate; Nelfinavir mesylate; Nelfinavir mesylate hydrate; Nelfinavir; NELFINAVIR MESYLATE AG1343; Nelfinavir [INN:BAN]; (3S-(2(2S*,3S*),3alpha,4abeta,8abeta))-N-(1,1-Dimethylethyl)decahydro-2-(2-hydroxy-3-((3-hydroxy-2-methylbenzoyl)amino)-4-(phenylthio)butyl)-3-isoquinolinecarboxamide; 159989-64-7; 1UN; 2-[2-HYDROXY-3-(3-HYDROXY-2-METHYL-BENZOYLAMINO)-4-PHENYL SULFANYL-BUTYL]-DECAHYDRO-ISOQUINOLINE-3-CARBOXYLIC ACID TERT-BUTYLAMIDE; C32H45N3O4S; CHEBI:7496; HO3OGH5D7I; NLF; UNII-HO3OGH5D7I; 98D603VP8V; C32H45N3O4S.CH4O3S; CHEBI:7497; CHEMBL1205; DSSTox_CID_10777; DSSTox_GSID_33736; DSSTox_RID_79093; HSDB 7159; MFCD00931436; Nelfinavir methanesulfonate hydrate; UNII-98D603VP8V
Indication Human immunodeficiency virus infection [ICD11: 1C60] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 663.9 Topological Polar Surface Area 190
Heavy Atom Count 45 Rotatable Bond Count 10
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
64142
ChEBI ID
CHEBI:7497
CAS Number
159989-65-8
Formula
C33H49N3O7S2
Canonical SMILES
CC1=C(C=CC=C1O)C(=O)NC(CSC2=CC=CC=C2)C(CN3CC4CCCCC4CC3C(=O)NC(C)(C)C)O.CS(=O)(=O)O
InChI
1S/C32H45N3O4S.CH4O3S/c1-21-25(15-10-16-28(21)36)30(38)33-26(20-40-24-13-6-5-7-14-24)29(37)19-35-18-23-12-9-8-11-22(23)17-27(35)31(39)34-32(2,3)4;1-5(2,3)4/h5-7,10,13-16,22-23,26-27,29,36-37H,8-9,11-12,17-20H2,1-4H3,(H,33,38)(H,34,39);1H3,(H,2,3,4)/t22-,23+,26-,27-,29+;/m0./s1
InChIKey
NQHXCOAXSHGTIA-SKXNDZRYSA-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
2-methoxy-3-hydroxynelfinavir DM002152
3008857
Unclear 1 [5]
3,4-Dihydroxynelfinavir DM002151
154699909
Oxidation - Hydroxylation 1 [5]
Nelfinavir hydroxyl-t- butylamide DM002150
475066
Oxidation - Hydroxylation 1 [6] , [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001719 Nelfinavir mesylate Nelfinavir hydroxyl-t- butylamide Oxidation - Hydroxylation CYP2C19 [6], [7]
MR001720 Nelfinavir mesylate 3,4-Dihydroxynelfinavir Oxidation - Hydroxylation CYP3A4 [5]
MR001721 Nelfinavir mesylate 2-methoxy-3-hydroxynelfinavir Unclear CYP3A4 [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]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
References
1 Nelfinavir Mesylate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 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.
3 Differential inhibition of cytochrome P450 3A4, 3A5 and 3A7 by five human immunodeficiency virus (HIV) protease inhibitors in vitro. Basic Clin Pharmacol Toxicol. 2006 Jan;98(1):79-85.
4 Impact of CYP2C19 polymorphism on the pharmacokinetics of nelfinavir in patients with pancreatic cancer. Br J Clin Pharmacol. 2015 Aug;80(2):267-75.
5 Conversion of the HIV protease inhibitor nelfinavir to a bioactive metabolite by human liver CYP2C19 Drug Metab Dispos. 2004 Dec;32(12):1462-7. doi: 10.1124/dmd.104.001743.
6 Effect of CYP2C19 polymorphism on nelfinavir to M8 biotransformation in HIV patients Br J Clin Pharmacol. 2008 Apr;65(4):548-57. doi: 10.1111/j.1365-2125.2007.03039.x.
7 Nelfinavir and Its Active Metabolite M8 Are Partial Agonists and Competitive Antagonists of the Human Pregnane X Receptor Mol Pharmacol. 2021 Mar;99(3):184-196. doi: 10.1124/molpharm.120.000116.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.