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Showing drug card for Nelfinavir (DB00220)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:39
Primary Accession Number DB00220
Secondary Accession Number
  • APRD00003
Name Nelfinavir
Drug Type
  • Approved
  • Small Molecule
Description A potent HIV protease inhibitor. It is used in combination with other antiviral drugs in the treatment of HIV in both adults and children. [PubChem]
Synonyms
  1. 1UN
  2. NFV
  3. NLF
  4. Nelfinavir mesylate
Brand Names
  1. Viracept
Brand Mixtures Not Available
Chemical 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
Chemical Formula C32H45N3O4S
Chemical Structure Structure
CAS Registry Number 159989-64-7
InChI Identifier InChI=1/C32H45N3O4S/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/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)/t22-,23+,26-,27-,29+/m0/s1/f/h33-34H
InChI Key QAGYKUNXZHXKMR-OJWIKGAMDR
KEGG Drug Not Available
KEGG Compound C07257 Link Image
PubChem Compound 64143 Link Image
PubChem Substance 206971 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02248761 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/nelfin.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/vir1483.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Nelfinavir Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 567.7820
Monoisotopic Molecular Weight 567.3131
State Solid
Melting Point 349.84 oC
Experimental Water Solubility Slightly soluble Source: PhysProp
Predicted Water Solubility 1.91e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 6 Source: PhysProp
Predicted LogP 4.62 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.47 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1ODW Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES CC1=C(C=CC=C1O)C(=O)N[C@@H](CSC1=CC=CC=C1)[C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C
Canonical SMILES CC1=C(C=CC=C1O)C(=O)NC(CSC1=CC=CC=C1)C(O)CN1CC2CCCCC2CC1C(=O)NC(C)(C)C
Drug Category
  • Anti-HIV Agents
  • HIV Protease Inhibitors
ATC Codes
AHFS Codes
  • 08:18.08.08
Indication Used in combination with other antiviral drugs in the treatment of HIV in both adults and children.
Pharmacology Nelfinavir is a protease inhibitor with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Protease inhibitors block the part of HIV called protease. HIV-1 protease is an enzyme required for the proteolytic cleavage of the viral polyprotein precursors into the individual functional proteins found in infectious HIV-1. Nelfinavir binds to the protease active site and inhibits the activity of the enzyme. This inhibition prevents cleavage of the viral polyproteins resulting in the formation of immature non-infectious viral particles. Protease inhibitors are almost always used in combination with at least two other anti-HIV drugs.
Mechanism of Action Nelfinavir inhibits the HIV viral proteinase enzyme which prevents cleavage of the gag-pol polyprotein, resulting in noninfectious, immature viral particles.
Absorption Well absorbed following oral administration.
Toxicity Oral LD50 is over 5g/kg in rats. Side effects include thirst and hunger, unexplained weight loss, increased urination, fatigue, and dry, itchy skin.
Protein Binding >98%
Biotransformation Primarily hepatic via cytochrome P450 (CYP450) enzymes. CYP3A and CYP2C19 appear to be the predominant enzymes that metabolize nelfinavir in humans. One major and several minor metabolites are found in plasma; the major oxidative metabolite has in vitro antiviral activity comparable to that of the parent drug.
Half Life 3.5 - 5 hours
Dosage Forms
Form Route
Powder Oral
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The protease inhibitor increases the anticoagulant effect
Alprazolam The protease inhibitor increases the effect of the benzodiazepine
Amiodarone Nelfinavir increases the effect and toxicity of amiodarone
Anisindione The protease inhibitor increases the anticoagulant effect
Aprepitant This CYP3A4 inhibitor increases the effect and toxicity of aprepitant
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atorvastatin Nelfinavir increases the effect and toxicity of the statin
Chlordiazepoxide The protease inhibitor increases the effect of the benzodiazepine
Ciclesonide Increased effects/toxicity of ciclesonide
Cisapride Increased risk of cardiotoxicity and arrhythmias
Clonazepam The protease inhibitor increases the effect of the benzodiazepine
Clorazepate The protease inhibitor increases the effect of the benzodiazepine
Cyclosporine The protease inhibitor increases the effect of cyclosporine
Darifenacin This potent CYP3A4 inhibitor slows darifenacin / solifenacin metabolism
Diazepam The protease inhibitor increases the effect of the benzodiazepine
Dicumarol The protease inhibitor increases the anticoagulant effect
Dihydroergotamine Nelfinavir increases the effect and toxicity of ergot derivative
Dihydroquinidine barbiturate Nelfinavir increases the effect and toxicity of quindine
Eletriptan The protease inhibitor increases the effect and toxicity of eletriptan
Eplerenone The protease inhibitor increases the effect and toxicity of eplerenone
Ergotamine Nelfinavir increases the effect and toxicity of ergot derivative
Erlotinib This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Estazolam The protease inhibitor increases the effect of the benzodiazepine
Ethinyl Estradiol Ritonavir could decrease the contraceptive efficacy
Felodipine Nelfinavir increases the effect and toxicity of felodipine
Fentanyl The protease inhibitor increases the effect and toxicity of fentanyl
Flurazepam The protease inhibitor increases the effect of the benzodiazepine
Fusidic Acid The protease inhibitor increases the effect and toxicity of fusidic acid
Halazepam The protease inhibitor increases the effect of the benzodiazepine
Lovastatin Nelfinavir increases the effect and toxicity of the statin
Mestranol Ritonavir could decrease the contraceptive efficacy
Methadone Nelfinavir decreases the effect of methadone
Midazolam The protease inhibitor increases the effect of the benzodiazepine
Nevirapine Nevirapine decreases the effect of nelfinavir
Pimozide Nelfinavir increases the effect and toxicity of pimozide
Prazepam The protease inhibitor increases the effect of the benzodiazepine
Quazepam The protease inhibitor increases the effect of the benzodiazepine
Quinidine Nelfinavir increases the effect and toxicity of quinidine
Quinidine barbiturate Nelfinavir increases the effect and toxicity of quinidine
Ranolazine Increased levels of ranolazine - risk of toxicity
Rifampin Rifampin decreases the effect of nelfinavir
Sildenafil The protease inhibitor increases the effect and toxicity of sildenafil
Simvastatin Nelfinavir increases the effect and toxicity of the statin
Solifenacin This potent CYP3A4 inhibitor slows darifenacin / solifenacin metabolism
St. John's Wort St. John's Wort decreases the effect of indinavir
Sunitinib Possible increase in sunitinib levels
Tacrolimus The protease inhibitor increases the effect and toxicity of tacrolimus
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Triazolam The protease inhibitor increases the effect of the benzodiazepine
Vardenafil The protease inhibitor increases the effect and toxicity of vardenafil
Warfarin The protease inhibitor increases the anticoagulant effect
Food Interactions
  • Food significantly increases absorption (2 to 3 times).
  • Take with food.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
  4. PDRhealth Link Image
Organisms Affected
  • Human Immunodeficiency Virus
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2C19 (CYP2C19)
  2. Cytochrome P450 3A4 (CYP3A4)
  3. Cytochrome P450 2C9 (CYP2C9)
  4. Cytochrome P450 2B6 (CYP2B6)
Targets
  1. HIV-1 protease
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 1 Gene Name CYP2C19
Enzyme 1 SwissProt ID P33261 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Phase 1 Metabolizing Enzyme 2 [top]
Enzyme 2 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 2 Gene Name CYP3A4
Enzyme 2 SwissProt ID P08684 Link Image
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Phase 1 Metabolizing Enzyme 3 [top]
Enzyme 3 Name Cytochrome P450 2C9 (CYP2C9)
Enzyme 3 Gene Name CYP2C9
Enzyme 3 SwissProt ID P11712 Link Image
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 Protein Sequence >sp|P11712|CP2C9_HUMAN Cytochrome P450 2C9 (EC 1.14.13.80) 
MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDISKSLTNLSKV
YGPVFTLYFGLKPIVVLHGYEAVKEALIDLGEEFSGRGIFPLAERANRGFGIVFSNGKKW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFHKRFDYKDQQFLNLMEKLNENIKILSSPWIQICNNFSPIIDYFPGTHNKLLKNVAFM
KSYILEKVKEHQESMDMNNPQDFIDCFLMKMEKEKHNQPSEFTIESLENTAVDLFGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRSHMPYTDAVVHEVQRYID
LLPTSLPHAVTCDIKFRNYLIPKGTTILISLTSVLHDNKEFPNPEMFDPHHFLDEGGNFK
KSKYFMPFSAGKRICVGEALAGMELFLFLTSILQNFNLKSLVDPKNLDTTPVVNGFASVP
PFYQLCFIPV
Phase 1 Metabolizing Enzyme 4 [top]
Enzyme 4 Name Cytochrome P450 2B6 (CYP2B6)
Enzyme 4 Gene Name CYP2B6
Enzyme 4 SwissProt ID P20813 Link Image
Enzyme 4 SNPs SNPJam Report Link Image
Enzyme 4 Protein Sequence >sp|P20813|CP2B6_HUMAN Cytochrome P450 2B6 (EC 1.14.14.1) 
MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRGLLKSFLRFRE
KYGDVFTVHLGPRPVVMLCGVEAIREALVDKAEAFSGRGKIAMVDPFFRGYGVIFANGNR
WKVLRRFSVTTMRDFGMGKRSVEERIQEEAQCLIEELRKSKGALMDPTFLFQSITANIIC
SIVFGKRFHYQDQEFLKMLNLFYQTFSLISSVFGQLFELFSGFLKYFPGAHRQVYKNLQE
INAYIGHSVEKHRETLDPSAPKDLIDTYLLHMEKEKSNAHSEFSHQNLNLNTLSLFFAGT
ETTSTTLRYGFLLMLKYPHVAERVYREIEQVIGPHRPPELHDRAKMPYTEAVIYEIQRFS
DLLPMGVPHIVTQHTSFRGYIIPKDTEVFLILSTALHDPHYFEKPDAFNPDHFLDANGAL
KKTEAFIPFSLGKRICLGEGIARAELFLFFTTILQNFSMASPVAPEDIDLTPQECGVGKI
PPTYQIRFLPR
Drug Target 1 [top]
Target 1 ID 731
Target 1 Name HIV-1 protease
Target 1 Synonyms
  1. Fragment
Target 1 Gene Name HIV-1 protease
Target 1 Protein Sequence >HIV-1 protease 
PQVTLWQRPIVTIKIGGQLKEALLDTGADDTVLEEMSLPGKWKPKMIGGIGGFIKVRQYD
QVSIEICGHKAIGTVLIGPTPVNIIGRNLLTQLGCTLNF
Target 1 Number of Residues 100
Target 1 Molecular Weight 10725
Target 1 Theoretical pI 8.77
Target 1 GO Classification
Function
catalytic activity
hydrolase activity
peptidase activity
endopeptidase activity
aspartic-type endopeptidase activity
Process
physiological process
metabolism
macromolecule metabolism
protein metabolism
cellular protein metabolism
proteolysis
Component
Not Available
Target 1 General Function Involved in aspartic-type endopeptidase activity
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 4377614 Link Image
Target 1 UniProtKB/Swiss-Prot ID O90777 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name O90777_9PLVG Link Image
Target 1 PDB ID 1ODW Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >297 bp 
CCTCAGGTCACTCTTTGGCAACGACCCATAGTCACAATAAAGATAGGGGGGCAACTAAAG
GAAGCTCTATTAGATACAGGAGCAGATGATACAGTATTAGAAGAAATGAGTTTGCCAGGA
AAATGGAAACCAAAAATGATAGGGGGAATTGGAGGTTTTATCAAAGTAAGACAGTATGAT
CAGGTATCCATAGAAATCTGCGGACATAAAGCTATAGGTACAGTATTAATAGGACCTACA
CCTGTCAACATAATTGGAAGGAATCTGTTGACTCAGCTTGGCTGCACTTTAAATTTT
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Servais J, Lambert C, Fontaine E, Plesseria JM, Robert I, Arendt V, Staub T, Schneider F, Hemmer R, Burtonboy G, Schmit JC: Comparison of DNA sequencing and a line probe assay for detection of human immunodeficiency virus type 1 drug resistance mutations in patients failing highly active antiretroviral therapy. J Clin Microbiol. 2001 Feb;39(2):454-9. [PubMed Link Image]
  2. Servais J, Lambert C, Fontaine E, Plesseria JM, Robert I, Arendt V, Staub T, Schneider F, Hemmer R, Burtonboy G, Schmit JC: Variant human immunodeficiency virus type 1 proteases and response to combination therapy including a protease inhibitor. Antimicrob Agents Chemother. 2001 Mar;45(3):893-900. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. Dandache S, Sevigny G, Yelle J, Stranix BR, Parkin N, Schapiro JM, Wainberg MA, Wu JJ: In Vitro Antiviral Activity and Cross-Resistance Profile of PL-100, a Next Generation Protease Inhibitor of Human Immunodeficiency Virus Type 1. Antimicrob Agents Chemother. 2007 Jul 16;. [PubMed Link Image]
  4. Wittayanarakul K, Hannongbua S, Feig M: Accurate prediction of protonation state as a prerequisite for reliable MM-PB(GB)SA binding free energy calculations of HIV-1 protease inhibitors. J Comput Chem. 2007 Sep 11;. [PubMed Link Image]
  5. Garriga C, Perez-Elias MJ, Delgado R, Ruiz L, Najera R, Pumarola T, Alonso-Socas Mdel M, Garcia-Bujalance S, Menendez-Arias L: Mutational patterns and correlated amino acid substitutions in the HIV-1 protease after virological failure to nelfinavir- and lopinavir/ritonavir-based treatments. J Med Virol. 2007 Nov;79(11):1617-28. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.