You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameEnfuvirtide
Accession NumberDB00109  (BTD00106, BIOD00106)
TypeBiotech
GroupsApproved, Investigational
DescriptionEnfuvirtide is a 36 residue synthetic peptide that inhibits HIV-1 fusion with CD4 cells. It is an N-terminal acetylated, C-terminal amide. As an HIV fusion inhibitor, it is the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection.
Protein structureDb00109
Related Articles
Protein chemical formulaC204H301N51O64
Protein average weight4491.876 Da
Sequences
>DB00109 sequence
YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWF
Download FASTA Format
Synonyms
Envelope polyprotein GP160 precursor [Contains: Exterior membrane glycoprotein,GP120, Transmembrane glycoprotein,GP41]
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FuzeonKitGenentech, Inc.2012-04-10Not applicableUs
FuzeonPowder, for solution108 mgSubcutaneousHoffmann La Roche Limited2003-08-18Not applicableCanada
FuzeonInjection, powder, for solution90 mg/mlSubcutaneousRoche Registration Limited2003-05-27Not applicableEu
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII19OWO1T3ZE
CAS number159519-65-0
Pharmacology
IndicationEnfuvirtide is an antiretroviral drug used in combination therapy for the treatment of HIV-1/AIDS.
Structured Indications
PharmacodynamicsNot Available
Mechanism of actionEnfuvirtide binds to the first heptad-repeat (HR1) in the gp41 subunit of the viral envelope glycoprotein and prevents the conformational changes required for the fusion of viral and cellular membranes. It works by disrupting the HIV-1 molecular machinery at the final stage of fusion with the target cell, preventing uninfected cells from becoming infected. Enfuvirtide is a biomimetic peptide that was rationally designed to mimic components of the HIV-1 fusion machinery and displace them, preventing normal fusion.
TargetKindPharmacological actionActionsOrganismUniProt ID
Envelope glycoproteinProteinyesNot AvailableHuman immunodeficiency virus 1Q53I07 details
Related Articles
AbsorptionAfter a 90 mg single subcutaneous injection of Enfuvirtide into the abdomen in 12 HIV-1 infected subjects, the mean peak concentration is 4.59+/-1.5 ug/ml and the median time to peak concentration was 8 hours (ranged from 3 to12 hours).
Volume of distribution
  • 5.5 ± 1.1 L
Protein binding92%
Metabolism

Expected to undergo catabolism to its constituent amino acids, with subsequent recycling of the amino acids in the body pool.

Route of eliminationNot Available
Half life3.8 +/- 0.6 hrs
Clearance
  • 24.8 +/- 4.1 mL/h/kg [HIV-1 infected adult and pediatric subjects following a 90-mg single SC dose of enfuvirtide]
  • 30.6 +/- 10.6 mL/h/kg [Following 90-mg twice daily dosing of FUZEON SC in combination with other antiretroviral agents in HIV-1 infected subjects]
  • 40 +/- 17 mL/h/kg [pediatric patients in the presence of concomitant medications including antiretroviral agents receiving the 2 mg/kg twice daily dose]
ToxicityNot Available
Affected organisms
  • Human Immunodeficiency Virus
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Enfuvirtide can be increased when it is combined with 1,10-Phenanthroline.Experimental
3,4-DichloroisocoumarinThe serum concentration of Enfuvirtide can be increased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDEThe serum concentration of Enfuvirtide can be increased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
AbirateroneThe metabolism of Enfuvirtide can be decreased when combined with Abiraterone.Approved
AlogliptinThe serum concentration of Enfuvirtide can be increased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Enfuvirtide can be increased when it is combined with Alpha-1-proteinase inhibitor.Approved
AmprenavirThe serum concentration of Enfuvirtide can be increased when it is combined with Amprenavir.Approved
Antithrombin III humanThe serum concentration of Enfuvirtide can be increased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Enfuvirtide can be increased when it is combined with Apixaban.Approved
AprotininThe serum concentration of Enfuvirtide can be increased when it is combined with Aprotinin.Approved, Withdrawn
ArgatrobanThe serum concentration of Enfuvirtide can be increased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe metabolism of Enfuvirtide can be decreased when combined with Armodafinil.Approved, Investigational
AsunaprevirThe serum concentration of Enfuvirtide can be increased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Enfuvirtide can be increased when it is combined with Atazanavir.Approved, Investigational
BatimastatThe serum concentration of Enfuvirtide can be increased when it is combined with Batimastat.Experimental
BenazeprilThe serum concentration of Enfuvirtide can be increased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Enfuvirtide can be increased when it is combined with Benzamidine.Experimental
Bi201335The serum concentration of Enfuvirtide can be increased when it is combined with Bi201335.Investigational
BivalirudinThe serum concentration of Enfuvirtide can be increased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Enfuvirtide can be increased when it is combined with Boceprevir.Approved
BortezomibThe metabolism of Enfuvirtide can be decreased when combined with Bortezomib.Approved, Investigational
CandoxatrilThe serum concentration of Enfuvirtide can be increased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Enfuvirtide can be increased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Enfuvirtide can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Enfuvirtide can be increased when combined with Carbamazepine.Approved, Investigational
ChloramphenicolThe metabolism of Enfuvirtide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Enfuvirtide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
ChymostatinThe serum concentration of Enfuvirtide can be increased when it is combined with Chymostatin.Experimental
CilastatinThe serum concentration of Enfuvirtide can be increased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Enfuvirtide can be increased when it is combined with Cilazapril.Approved
CimetidineThe metabolism of Enfuvirtide can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Enfuvirtide can be decreased when combined with Citalopram.Approved
ClotrimazoleThe metabolism of Enfuvirtide can be decreased when combined with Clotrimazole.Approved, Vet Approved
Cyproterone acetateThe serum concentration of Enfuvirtide can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Dabigatran etexilateThe serum concentration of Enfuvirtide can be increased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Enfuvirtide can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Enfuvirtide can be increased when it is combined with Darunavir.Approved
DelavirdineThe metabolism of Enfuvirtide can be decreased when combined with Delavirdine.Approved
DisulfiramThe metabolism of Enfuvirtide can be decreased when combined with Disulfiram.Approved
EcabetThe serum concentration of Enfuvirtide can be increased when it is combined with Ecabet.Approved, Investigational
EdoxabanThe serum concentration of Enfuvirtide can be increased when it is combined with Edoxaban.Approved
EfavirenzThe metabolism of Enfuvirtide can be decreased when combined with Efavirenz.Approved, Investigational
ElafinThe serum concentration of Enfuvirtide can be increased when it is combined with Elafin.Investigational
EnalaprilThe serum concentration of Enfuvirtide can be increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Enfuvirtide can be increased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Enfuvirtide can be increased when it is combined with Enalkiren.Experimental
Eslicarbazepine acetateThe metabolism of Enfuvirtide can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Enfuvirtide can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Enfuvirtide can be decreased when combined with Etravirine.Approved
FluconazoleThe metabolism of Enfuvirtide can be decreased when combined with Fluconazole.Approved
FluoxetineThe metabolism of Enfuvirtide can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Enfuvirtide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe serum concentration of Enfuvirtide can be increased when it is combined with Fosamprenavir.Approved
FosinoprilThe serum concentration of Enfuvirtide can be increased when it is combined with Fosinopril.Approved
FosphenytoinThe metabolism of Enfuvirtide can be increased when combined with Fosphenytoin.Approved
GabexateThe serum concentration of Enfuvirtide can be increased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Enfuvirtide can be increased when it is combined with Geldanamycin.Experimental
GemfibrozilThe metabolism of Enfuvirtide can be decreased when combined with Gemfibrozil.Approved
GM6001The serum concentration of Enfuvirtide can be increased when it is combined with GM6001.Experimental
HirulogThe serum concentration of Enfuvirtide can be increased when it is combined with Hirulog.Experimental
idraparinuxThe serum concentration of Enfuvirtide can be increased when it is combined with idraparinux.Investigational
ImidaprilThe serum concentration of Enfuvirtide can be increased when it is combined with Imidapril.Investigational
IndinavirThe serum concentration of Enfuvirtide can be increased when it is combined with Indinavir.Approved
IsoflurophateThe serum concentration of Enfuvirtide can be increased when it is combined with Isoflurophate.Approved, Withdrawn
IsoniazidThe metabolism of Enfuvirtide can be decreased when combined with Isoniazid.Approved
IxazomibThe serum concentration of Enfuvirtide can be increased when it is combined with Ixazomib.Approved
KetoconazoleThe metabolism of Enfuvirtide can be decreased when combined with Ketoconazole.Approved, Investigational
LepirudinThe serum concentration of Enfuvirtide can be increased when it is combined with Lepirudin.Approved
LinagliptinThe serum concentration of Enfuvirtide can be increased when it is combined with Linagliptin.Approved
LisinoprilThe serum concentration of Enfuvirtide can be increased when it is combined with Lisinopril.Approved, Investigational
LopinavirThe serum concentration of Enfuvirtide can be increased when it is combined with Lopinavir.Approved
LuliconazoleThe serum concentration of Enfuvirtide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Enfuvirtide can be decreased when it is combined with Lumacaftor.Approved
MoclobemideThe metabolism of Enfuvirtide can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Enfuvirtide can be decreased when combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Enfuvirtide can be increased when it is combined with Moexipril.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Enfuvirtide can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Enfuvirtide can be increased when it is combined with Nafamostat.Investigational
NCX 4016The serum concentration of Enfuvirtide can be increased when it is combined with NCX 4016.Investigational
NelfinavirThe serum concentration of Enfuvirtide can be increased when it is combined with Nelfinavir.Approved
NicardipineThe metabolism of Enfuvirtide can be decreased when combined with Nicardipine.Approved
NicotineThe metabolism of Enfuvirtide can be decreased when combined with Nicotine.Approved
NitroaspirinThe serum concentration of Enfuvirtide can be increased when it is combined with Nitroaspirin.Investigational
OmapatrilatThe serum concentration of Enfuvirtide can be increased when it is combined with Omapatrilat.Investigational
OmeprazoleThe metabolism of Enfuvirtide can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OtamixabanThe serum concentration of Enfuvirtide can be increased when it is combined with Otamixaban.Investigational
PantoprazoleThe metabolism of Enfuvirtide can be decreased when combined with Pantoprazole.Approved
PerindoprilThe serum concentration of Enfuvirtide can be increased when it is combined with Perindopril.Approved
PhenytoinThe metabolism of Enfuvirtide can be increased when combined with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Enfuvirtide can be increased when it is combined with Phosphoramidon.Experimental
PrinomastatThe serum concentration of Enfuvirtide can be increased when it is combined with Prinomastat.Investigational
QuinaprilThe serum concentration of Enfuvirtide can be increased when it is combined with Quinapril.Approved, Investigational
RacecadotrilThe serum concentration of Enfuvirtide can be increased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Enfuvirtide can be increased when it is combined with Ramipril.Approved
RemikirenThe serum concentration of Enfuvirtide can be increased when it is combined with Remikiren.Approved
RifampicinThe metabolism of Enfuvirtide can be increased when combined with Rifampicin.Approved
RitonavirThe serum concentration of Enfuvirtide can be increased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Enfuvirtide can be increased when it is combined with Rivaroxaban.Approved
SaquinavirThe serum concentration of Enfuvirtide can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Enfuvirtide can be increased when it is combined with Saxagliptin.Approved
SertralineThe metabolism of Enfuvirtide can be decreased when combined with Sertraline.Approved
SimeprevirThe serum concentration of Enfuvirtide can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Enfuvirtide can be increased when it is combined with Sitagliptin.Approved, Investigational
SpiraprilThe serum concentration of Enfuvirtide can be increased when it is combined with Spirapril.Approved
StiripentolThe metabolism of Enfuvirtide can be decreased when combined with Stiripentol.Approved
TelaprevirThe serum concentration of Enfuvirtide can be increased when it is combined with Telaprevir.Approved
TemocaprilThe serum concentration of Enfuvirtide can be increased when it is combined with Temocapril.Experimental, Investigational
ThiorphanThe serum concentration of Enfuvirtide can be increased when it is combined with Thiorphan.Experimental
TiclopidineThe metabolism of Enfuvirtide can be decreased when combined with Ticlopidine.Approved
TipranavirThe serum concentration of Enfuvirtide can be increased when it is combined with Tipranavir.Approved, Investigational
TopiramateThe metabolism of Enfuvirtide can be decreased when combined with Topiramate.Approved
TrandolaprilThe serum concentration of Enfuvirtide can be increased when it is combined with Trandolapril.Approved
TranylcypromineThe metabolism of Enfuvirtide can be decreased when combined with Tranylcypromine.Approved
UbenimexThe serum concentration of Enfuvirtide can be increased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Enfuvirtide can be increased when it is combined with Ulinastatin.Investigational
VildagliptinThe serum concentration of Enfuvirtide can be increased when it is combined with Vildagliptin.Approved, Investigational
VoriconazoleThe metabolism of Enfuvirtide can be decreased when combined with Voriconazole.Approved, Investigational
XimelagatranThe serum concentration of Enfuvirtide can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The serum concentration of Enfuvirtide can be increased when it is combined with Ym150.Investigational
Food InteractionsNot Available
References
Synthesis Reference

Ananda Kuppanna, Reddy Maria Bhaskar Reddy Komma, Debashish Datta. An improved process for the preparation of enfuvirtide. WO2011095989A2 (Issued Aug 11, 2011).

General References
  1. Greenberg ML, Cammack N: Resistance to enfuvirtide, the first HIV fusion inhibitor. J Antimicrob Chemother. 2004 Aug;54(2):333-40. Epub 2004 Jul 1. [PubMed:15231762 ]
External Links
ATC CodesJ05AX07
AHFS Codes
  • 08:18.08.04
PDB Entries
FDA labelDownload (153 KB)
MSDSNot Available
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionSubcutaneous90 mg/ml
Kit
Powder, for solutionSubcutaneous108 mg
Prices
Unit descriptionCostUnit
Fuzeon convenience kit3062.23USD kit
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2224008 No2009-08-182016-06-06Canada
US5464933 No1993-06-072013-06-07Us
US6475491 No1995-06-072015-06-07Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
hydrophobicity-0.875Not Available
isoelectric point4.30Not Available
Taxonomy
DescriptionNot Available
KingdomOrganic Compounds
Super ClassOrganic Acids
ClassCarboxylic Acids and Derivatives
Sub ClassAmino Acids, Peptides, and Analogues
Direct ParentPeptides
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human immunodeficiency virus 1
Pharmacological action
yes
General Function:
Structural molecule activity
Specific Function:
Not Available
Gene Name:
gp41
Uniprot ID:
Q53I07
Molecular Weight:
16767.98 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
  3. Cabrera C, Marfil S, Garcia E, Martinez-Picado J, Bonjoch A, Bofill M, Moreno S, Ribera E, Domingo P, Clotet B, Ruiz L: Genetic evolution of gp41 reveals a highly exclusive relationship between codons 36, 38 and 43 in gp41 under long-term enfuvirtide-containing salvage regimen. AIDS. 2006 Oct 24;20(16):2075-80. [PubMed:17053353 ]
  4. Mink M, Mosier SM, Janumpalli S, Davison D, Jin L, Melby T, Sista P, Erickson J, Lambert D, Stanfield-Oakley SA, Salgo M, Cammack N, Matthews T, Greenberg ML: Impact of human immunodeficiency virus type 1 gp41 amino acid substitutions selected during enfuvirtide treatment on gp41 binding and antiviral potency of enfuvirtide in vitro. J Virol. 2005 Oct;79(19):12447-54. [PubMed:16160172 ]
  5. Aquaro S, D'Arrigo R, Svicher V, Perri GD, Caputo SL, Visco-Comandini U, Santoro M, Bertoli A, Mazzotta F, Bonora S, Tozzi V, Bellagamba R, Zaccarelli M, Narciso P, Antinori A, Perno CF: Specific mutations in HIV-1 gp41 are associated with immunological success in HIV-1-infected patients receiving enfuvirtide treatment. J Antimicrob Chemother. 2006 Oct;58(4):714-22. Epub 2006 Aug 5. [PubMed:16891628 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Patel IH, Zhang X, Nieforth K, Salgo M, Buss N: Pharmacokinetics, pharmacodynamics and drug interaction potential of enfuvirtide. Clin Pharmacokinet. 2005;44(2):175-86. [PubMed:15656696 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Patel IH, Zhang X, Nieforth K, Salgo M, Buss N: Pharmacokinetics, pharmacodynamics and drug interaction potential of enfuvirtide. Clin Pharmacokinet. 2005;44(2):175-86. [PubMed:15656696 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23