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
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
NQHXCOAXSHGTIA-SKXNDZRYSA-N
InChIKey
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
Cross-matching ID
PubChem CID
64142
ChEBI ID
CHEBI:7497
CAS Number
159989-65-8
INTEDE ID
DR1138
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
Adiponectin (ADIPOQ) OTNX23LE ADIPO_HUMAN Gene/Protein Processing [4]
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [5]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Regulation of Drug Effects [6]
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Drug Response [6]
Bile salt export pump (ABCB11) OTRU7THO ABCBB_HUMAN Gene/Protein Processing [7]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2) OTW8V2V1 ABCG2_HUMAN Gene/Protein Processing [6]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [4]
C-C motif chemokine 3 (CCL3) OTW2H3ND CCL3_HUMAN Gene/Protein Processing [4]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [8]
Caspase-7 (CASP7) OTAPJ040 CASP7_HUMAN Gene/Protein Processing [8]
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 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.
5 Binding of anti-HIV drugs to human serum albumin. IUBMB Life. 2004 Oct;56(10):609-14. doi: 10.1080/15216540400016286.
6 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.
7 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.
8 The mitochondria-independent cytotoxic effect of nelfinavir on leukemia cells can be enhanced by sorafenib-mediated mcl-1 downregulation and mitochondrial membrane destabilization. Mol Cancer. 2010 Jan 27;9:19. doi: 10.1186/1476-4598-9-19.