ChemicalBook > CAS DataBase List > Enfuvirtide

Enfuvirtide

Description Background

Product Name: Enfuvirtide
CAS No.: 159519-65-0
Chemical Name: Enfuvirtide
Synonyms: Enf;Aids059486;Enfvectide;Enfuviride;Aids-059486;Enfuvirtide;Pentafuside;Fuzeon (tm);Gp41 127-162 aa;Enfuvirtide; T-2
CBNumber: CB7358557
Molecular Formula: C204H301N51O64
Formula Weight: 4491.92
MOL File: 159519-65-0.mol

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Enfuvirtide Property

storage temp.: -20°C
solubility: DMF: 5 mg/ml; DMSO: 5 mg/ml; PBS (pH 7.2): 2 mg/ml
form: powder
color: white to off-white
Sequence: Ac-Tyr-Thr-Ser-Leu-Ile-His-Ser-Leu-Ile-Glu-Glu-Ser-Gln-Asn-Gln-Gln-Glu-Lys
InChIKey: PEASPLKKXBYDKL-HVYTUBITNA-N

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Safety

WGK Germany: 3
HS Code: 3504009000
Hazardous Substances Data: 159519-65-0(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0934
Product name: Enfuvirtide acetate salt
Purity: ≥95% (HPLC)
Packaging: 5mg
Price: $121
Updated: 2025/07/31

Cayman Chemical

Product number: 24097
Product name: Enfuvirtide
Purity: ≥98%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 24097
Product name: Enfuvirtide
Purity: ≥98%
Packaging: 5mg
Price: $109
Updated: 2024/03/01

Cayman Chemical

Product number: 24097
Product name: Enfuvirtide
Purity: ≥98%
Packaging: 10mg
Price: $199
Updated: 2024/03/01

AK Scientific

Product number: H659
Product name: Enfuvirtideacetate
Packaging: 5mg
Price: $218
Updated: 2021/12/16

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Enfuvirtide Chemical Properties,Usage,Production

Description

Enfuvirtide is the first of a new class of HIV therapeutics that interferes with the entry of HIV-1 by inhibiting fusion of viral and cellular membranes. It binds to the first heptad-repeat (HR1) in ghe gp41 subunit of the viral envelope glycoprotein and prevents the conformational changes required for the fusion with cell membranes, thus representing a new mechanism. It is a potent inhibitor of this binding with an IC50 in laboratory and primary isolates (HIV-1 clades A–G) ranging from 4 to 280 nM (18–1260 ng/mL), but has virtually no activity against HIV-2. Due to its unique mechanism, it does not show cross-resistance to NRTI, NNRTI and PIs. It is prepared by chemical synthesis, using a combination of solution and solid phase steps. The solid phase steps utilize fmoc protection and the acid sensitive 2- chlorotrityl chloride resin to produce peptides of lengths ranging from nine to sixteen amino acids. These amino acids are subsequently coupled to form the full-length peptide followed by side-chain deprotection and column chromatography. In the HuPBMC-SCID mouse model of HIV-1 infection enfuvirtide showed a dosedependent decrease in viral load. At doses of 200 mg/kg/day, it decreased the RNA levels to 8.2 copies/1 million cells compared to 17 million copies/1 million cells in the saline-treated group. In a clinical study involving 78 heavily pretreated patients (plasma HIV RNA＞5000 copies/mL), enfuvirtide dosing of 12.5–200 mg/day by b.i.d. subcutaneous injection resulted in a dose-dependent decrease in viral load (plasma HIV RNA 0.3–1.6 log 10 copies/mL). In a combination drug study where all patients received an optimized retroviral regimen with or without enfuvirtide, it was found that, at week 24, the enfuvirtide group had a 4.5 fold-relative drop in HIV RNA copies/mL relative to the standard treatment group. Subjects received 3–5 antiretroviral agents with or without enfuvirtide. In clinical trials, HIV-1 isolates from 185 patients using enfuvirtide in a cocktail with other antiretroviral agents showed 4 to 422-fold decrease in sensitivity to this drug. These more resistant types had changes in the gp41 amino acids 36–45. Enfuvirtide is dosed twice per day (90 mg) by subcutaneous injection and has an elimination half-life of about 3.8 h. It is highly plasma protein bound (92%) and has a Vdss is 5.5 L. Local injection site irritation (98% had at least one reaction), diarrhea (26.8%), nausea (20.1%), and fatigue (16.1%) were the most common adverse events.

Description

Enfuvirtide is a biomimetic peptide inhibitor of HIV-1 fusion with CD4⁺ cells. It inhibits HIV-1 infectivity of HeLa cells stably expressing CD4 by the HXB2 strain (IC₅₀ = 692 pM) and by clinical isolates (IC₉₀s = 6.1-61 nM) in a single-cycle infectivity assay. It also inhibits genomic integration of HIV-1 into human intraepithelial vaginal cells and peripheral blood mononuclear cells (PBMCs; IC₅₀s = 51.2 and 13.58 μM, respectively). Enfuvirtide binds to a recombinant molecular mimic of HIV-1 glycoprotein gp41 that contains three N-terminal heptad and two C-terminal heptad repeat regions (K_d = 32 nM). It also binds to recombinant formyl peptide receptors (FPR) expressed in rat basophilic leukemia cells (IC₅₀ = 5 nM) and attracts and activates human peripheral blood phagocytes, but not T lymphocytes, in vitro when used at a concentration of 100 nM. Formulations containing enfuvirtide have been used in combination therapy for the treatment of HIV-1/AIDS.

Originator

Duke University (US)

Uses

Antiviral (blockade of gp-41 mediated membrane fusion). Fuzeon (Roche) [Note—The trivial name, pentafuside, has appeared in literature.

Definition

ChEBI: A synthetic 36-amino acid peptide consisting of N-acetyltyrosyl, threonyl, seryl, leucyl, isoleucyl, histidyl, seryl, leucyl, isoleucyl, alpha-glutamyl, alpha-glutamyl, seryl, glutaminyl, asparaginyl, glutaminyl, glutamin l, alpha-glutamyl, lysyl, asparaginyl, alpha-glutamyl, alpha-glutamyl, alpha-glutamyl, leucyl, leucyl, alpha-glutamyl, leucyl, alpha-aspartyl, lysyl, tryp ophyl, alanyl, seryl, leucyl, tryptophyl, asparaginyl, tryptophyl, and phenylalaninamide residues joined in sequence. An HIV fusion inhibitor, it was the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 nfection. It interferes with entry of HIV into cells by binding to the gp41 sub-unit of the viral envelope glycoprotein, so inhibiting fusion of viral and cellular membranes.

brand name

Fuzeon

Biological Functions

Enfuvirtide is used in combination with other antiretrovirals and works against a variety of HIV-1 variants, but it is not active against HIV-2. Resistance to enfuvirtide can develop when the virus produces changes in a 10-amino-acid domain between residues 36 to 45 in the gp41 HIV surface glycoprotein.

Acquired resistance

Resistance is mediated by amino acid substitutions within the first heptad repeat region of gp41 at amino acids 36–45. Resistance emerges fairly rapidly in patients experiencing virological failure with an enfuvirtide-containing antiretroviral regimen, and is associated with the return of the plasma HIV load toward baseline within a few weeks.

General Description

Enfuvirtide acetate salt is a linear synthetic peptide made of 36 amino acids. It has an acetylated N-terminus and a carboxamide C-terminus. Enfuvirtide is catabolized with the help of proteolytic enzymes.

Pharmaceutical Applications

A linear 36-amino acid synthetic peptide with an acetylated N-terminus and a carboxamide C-terminus. It is formulated as a lyophilized powder to be reconstituted for subcutaneous injection.

Biochem/physiol Actions

Enfuvirtide is an HIV fusion inhibitor used to patients with multi-drug resistant HIV. Enfuvirtide binds to gp41 preventing the creation of an entry pore for the HIV-1 virus.

Pharmacokinetics

Subcutaneous absorption c. 84.3%
C_max 90 mg s/c twice daily c. 4.59 mg/L
Plasma half-life c. 3.8 h
Volume of distribution 5.5 L
Plasma protein binding c. 92%
Absorption and distribution
Absorption of the 90 mg dose is comparable when injected into the subcutaneous tissue of the abdomen, thigh or arm. It does not penetrate the CSF or semen. Distribution into breast milk has not been described.
Metabolism and excretion
It probably undergoes catabolism to its constituent amino acids, with subsequent recycling of the amino acids in the body pool.

Clinical Use

Treatment of HIV infection (in combination with other antiretroviral drugs) in adults and children older than 6 years who show evidence of HIV-1 replication despite ongoing antiretroviral therapy

Side effects

It does not seem to have any long-term toxicities (including the HIV lipodystrophy syndrome) associated with other commonly used antiretrovirals. Reaction at the injection site, variously characterized by local pain, erythema, pruritus, induration, ecchymosis, nodules or cysts, is experienced by more than 90% of patients and may lead to treatment fatigue.

Drug interactions

Potentially hazardous interactions with other drugs Orlistat: absorption possibly reduced by orlistat.

Metabolism

As a peptide, enfuvirtide is expected to undergo catabolism to its constituent amino acids, with subsequent recycling of the amino acids in the body pool. In vitro human microsomal studies and in vivo studies indicate that enfuvirtide is not an inhibitor of CYP450 enzymes. In in vitro human microsomal and hepatocyte studies, hydrolysis of the amide group of the C-terminus amino acid, phenylalanine results in a deamidated metabolite. Mass balance studies to determine elimination pathway(s) of enfuvirtide have not been performed in humans.

Description

Enfuvirtide has an amino acid sequence Ac-Tyr-Thr-Ser-Leu-Ile-His-Ser-Leu-Ile-Glu-Glu-Ser-Gln-Asn-Gln-Gln-Glu-Lys-Asn-Glu-Gln-Glu-Leu-Leu-Glu-Leu-Asp-Lys-Trp-Ala-Ser-Leu-Trp-Asn-Trp-Phe-NH₂, molecular formula of C₂₀₄H₃₀₁N₅₁O₆₄ and a molecular weight of 4488.9 Dalton.

Background

Enfuvirtide also called human immunodeficiency fusion inhibitor blocks HIV’s ability to infect healthy CD4 cells. It can reduce the amount of HIV in the blood and increase the number of CD4 cells. Enfuvirtide operates by disrupting the HIV-1 molecular machinery at the final phase of fusion with the target cell, preventing uninfected cells from becoming infected. Enfuvirtide mimics components of the HIV-1 fusion apparatus and displace them, preventing normal fusion. HIV attaches to the host CD4+ cell receptor using the viral protein GP120; upon binding, GP120 deforms allowing the viral protein GP41 to insert itself into the host cell's plasma membrane. Entry inhibitors bind to GP41 preventing the formation of an entry pore for the capsid of the virus, keeping it out of the cell.

References

[1] PAOLO INGALLINELLA. Addition of a cholesterol group to an HIV-1 peptide fusion inhibitor dramatically increases its antiviral potency.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2009, 106 14: 5801-5806. DOI: 10.1073/pnas.0901007106
[2] M JULIANA MCELRATH. Ex vivo comparison of microbicide efficacies for preventing HIV-1 genomic integration in intraepithelial vaginal cells.[J]. Antimicrobial Agents and Chemotherapy, 2010, 54 2: 763-772. DOI: 10.1128/aac.00891-09
[3] KELLY CHAMPAGNE Michael J R Akira Shishido. Interactions of HIV-1 inhibitory peptide T20 with the gp41 N-HR coiled coil.[J]. The Journal of Biological Chemistry, 2009, 284 6: 3619-3627. DOI: 10.1074/jbc.m809269200
[4] S B SU. T20/DP178, an ectodomain peptide of human immunodeficiency virus type 1 gp41, is an activator of human phagocyte N-formyl peptide receptor.[J]. Blood, 1999, 93 11: 3885-3892.

Enfuvirtide Preparation Products And Raw materials

Raw materials

Preparation Products

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Enfuvirtide Suppliers

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View Lastest Price from Enfuvirtide manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Enfuvirtide 159519-65-0
Price: US $0.00/g
Min. Order: 1g
Purity: 98%min
Supply Ability: 1000g
Release date: 2023-01-12

Henan Aochuang Chemical Co.,Ltd.

Product: Enfuvirtide 159519-65-0
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 1Ton
Release date: 2022-10-11

Hebei Yanxi Chemical Co., Ltd.

Product: enfuvirtide 159519-65-0
Price: US $40.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-09-18

159519-65-0, EnfuvirtideRelated Search:

GRF (1-44) (HUMAN) Lecirelin Liraglutide Ornipressin Triptorelin Teriparatide acetate Amyloid β-Peptide (1-42) (human) CRF (HUMAN, RAT) Vasopressin Abarelix FERTIRELIN Octreotide Teriparatideacetate Enfuvirtide ENFUVIRTIDE ACETATE ENFUVIRTIDE (T-20) ENFUVIRTIDE (LEUCINE-D10) Enfuvirtide(T-20)CgmpPeptide

Enfuvirtide; T-2

Enfuvirtide Acetate (T-20)

ENFUVIRTIDE(T-20) 98+%

Enfurvitide(T-20)

Pentafuside

Ac-Tyr-Thr-Ser-Leu-Ile-His-Ser-Leu-Ile-Glu-Glu-Ser-Gln-Asn-Gln-Gln-Glu-Lys-Asn-Glu-Gln-Glu-Leu-Leu-Glu-Leu-Asp-Lys-Trp-Ala-Ser-Leu-Trp-Asn-Trp-Phe-NH{2}

Enfuvirtide

Aids059486

Aids-059486

Enf

Fuzeon (tm)

Gp41 127-162 aa

Enfuvirtide & Enfuvirtide Acetate

Ac-Tyr-Thr-Ser-Leu-Ile-His-Ser-Leu-Ile-Glu-Glu-Ser-Gln-Asn-Gln-Gln-Glu-Lys-Asn-Glu-Gln-Glu-Leu-Leu-Glu-Leu-Asp-Lys-Trp-Ala-Ser-Leu-Trp-Asn-Trp-Asn-Trp-Phe-NH2

T20, Pentafuside

Enfuvirtide acetate salt

T-20 acetate salt

Enfuvirtide(T-20) Acetate

Enfuvirtide,Ac-Tyr-Thr-Ser-Leu-Ile-His-Ser-Leu-Ile-Glu-Glu-Ser-Gln-Asn-Gln-Gln-Glu-Lys-Asn-Glu-Gln-Glu-Leu-Leu-Glu-Leu-Asp-Lys-Trp-Ala-Ser-Leu-Trp-Asn-Trp-Phe-NH2,Ac-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWF-NH2?, >95%

Enfuvirtide impurity

Well, wei peptide

Enfuvirtide USP/EP/BP

159519-65-0 Enfuvirtide Acetate (T-20)

Enfvectide

Enfuvirtide，Ac-Tyr-Thr-Ser-Leu-Ile-His-Ser-Leu-Ile-Glu-Glu-Ser-Gln-Asn-Gln-Gln-Glu-Lys-Asn-Glu-Gln-Glu-Leu-Leu-Glu-Leu-Asp-Lys-Trp-Ala-Ser-Leu-Trp-Asn-Trp-Phe-NH2，Ac-YTSLIHSLIEESQNQQEKNEQELLELDKWASLWNWF-NH2

Enfuvirtide, Pentafuside

Enfuvirtide, Pentafuside, T20

N-Acetyl-L-tyrosyl-L-threonyl-L-seryl-L-leucyl-L-isoleucyl-L-histidyl-L-seryl-L-leucyl-L-isoleucyl-L-α-glutamyl-L-α-glutamyl-L-seryl-L-glutaminyl-L-asparaginyl-L-glutaminyl-L-glutaminyl-L-α-glutamyl-L-lysyl-L-asparaginyl-L-α-glutamyl-L-glutaminyl-L-α-glutamyl-L-leucyl-L-leucyl-L-α-glutamyl-L-leucyl-L-α-aspartyl-L-lysyl-L-tryptophyl-L-alanyl-L-seryl-L-leucyl-L-tryptophyl-L-asparaginyl-L-tryptophyl-L-phenylalaninamide

Enfuviride

Rabbit Anti-Enfuvirtide/Bio Conjugated antibody

Ticagrelor Impurity 227

159519-65-0

C204H301N51O64

proteins

Peptide