Details of the Drug

General Information of Drug (ID: DMFX6G8)

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
Affected Organisms
Human Immunodeficiency Virus
ATC Code
J05AE04: Nelfinavir mesylate
J05AE: Protease inhibitors
J05A: DIRECT ACTING ANTIVIRALS
J05: ANTIVIRALS FOR SYSTEMIC USE
J: ANTIINFECTIVES FOR SYSTEMIC USE
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski):
1		 Molecular Weight 663.9
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 10
Hydrogen Bond Donor Count 5
Hydrogen Bond Acceptor Count 9
Chemical Identifiers
Formula
C33H49N3O7S2
IUPAC Name
(3S,4aS,8aS)-N-tert-butyl-2-[(2R,3R)-2-hydroxy-3-[(3-hydroxy-2-methylbenzoyl)amino]-4-phenylsulfanylbutyl]-3,4,4a,5,6,7,8,8a-octahydro-1H-isoquinoline-3-carboxamide;methanesulfonic acid
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
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
Cross-matching ID
PubChem CID
64142
ChEBI ID
CHEMBL7497
CAS Number
159989-65-8
UNII
HO3OGH5D7I
DrugBank ID
DB00220
INTEDE ID
DR1138
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [1]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [2]
Cytochrome P450 3A5 (CYP3A5) DEIBDNY CP3A5_HUMAN Substrate [3]
Cytochrome P450 3A7 (CYP3A7) DERD86B CP3A7_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [4]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Drug Response [5]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [6]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [5]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [7]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [7]
Cyclic AMP-dependent transcription factor ATF-4 (ATF4) OTRFV19J ATF4_HUMAN Gene/Protein Processing [8]
Cyclic AMP-dependent transcription factor ATF-6 alpha (ATF6) OTAFHAVI ATF6A_HUMAN Protein Interaction/Cellular Processes [9]
DNA damage-inducible transcript 3 protein (DDIT3) OTI8YKKE DDIT3_HUMAN Gene/Protein Processing [8]
Eukaryotic translation initiation factor 2A (EIF2A) OTWXELQP EIF2A_HUMAN Post-Translational Modifications [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 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.
2 Impact of CYP2C19 polymorphism on the pharmacokinetics of nelfinavir in patients with pancreatic cancer. Br J Clin Pharmacol. 2015 Aug;80(2):267-75.
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 Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. doi: 10.1080/15216540400016286.
5 Influence of ABCB1, ABCC1, ABCC2, and ABCG2 haplotypes on the cellular exposure of nelfinavir in vivo. Pharmacogenet Genomics. 2005 Sep;15(9):599-608. doi: 10.1097/01.fpc.0000172241.42546.d3.
6 Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. Toxicol Sci. 2010 Dec; 118(2):485-500.
7 Some HIV antiretrovirals increase oxidative stress and alter chemokine, cytokine or adiponectin production in human adipocytes and macrophages. Antivir Ther. 2007;12(4):489-500.
8 Inhibin beta E is upregulated by drug-induced endoplasmic reticulum stress as a transcriptional target gene of ATF4. Toxicol Appl Pharmacol. 2012 Oct 15;264(2):300-4. doi: 10.1016/j.taap.2012.08.011. Epub 2012 Aug 23.
9 Nelfinavir induces liposarcoma apoptosis through inhibition of regulated intramembrane proteolysis of SREBP-1 and ATF6. Clin Cancer Res. 2011 Apr 1;17(7):1796-806. doi: 10.1158/1078-0432.CCR-10-3216. Epub 2011 Feb 25.
10 Nelfinavir induces the unfolded protein response in ovarian cancer cells, resulting in ER vacuolization, cell cycle retardation and apoptosis. Cancer Biol Ther. 2009 Feb;8(3):226-32. doi: 10.4161/cbt.8.3.7339. Epub 2009 Feb 3.