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Enfuvirtide

Enfuvirtide
Enfuvirtide structure
CAS No.
159519-65-0
Chemical Name:
Enfuvirtide
Synonyms
Enf;Aids059486;Aids-059486;Pentafuside;Enfuvirtide;Fuzeon (tm);Gp41 127-162 aa;Enfuvirtide; T-2;T20, Pentafuside;Enfurvitide(T-20)
CBNumber:
CB7358557
Molecular Formula:
C204H301N51O64
Formula Weight:
4491.92
MOL File:
159519-65-0.mol

Enfuvirtide Properties

storage temp. 
?20°C
form 
powder
color 
white to off-white
SAFETY
  • Risk and Safety Statements
WGK Germany  3

Enfuvirtide price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0934 Enfuvirtide acetate salt ≥95% (HPLC) 159519-65-0 5mg $92.1 2018-11-13 Buy
Cayman Chemical 24097 Enfuvirtide ≥98% 159519-65-0 1mg $25 2018-11-19 Buy
Cayman Chemical 24097 Enfuvirtide ≥98% 159519-65-0 5mg $88 2018-11-19 Buy
Cayman Chemical 24097 Enfuvirtide ≥98% 159519-65-0 10mg $163 2018-11-19 Buy

Enfuvirtide Chemical Properties,Uses,Production

Description

N-acetyl-L-tyrosyl-L-threonyl-L-seryl-L-leucyl-L-isoleucyl-L-histidyl-L-seryl-Lleucyl- L-isoleucyl-L-glutamyl-L-glutamyl-L-seryl-L-glutaminyl-L-asparaginyl-Lglutaminyl- L-glutaminyl-L-glutamy-L-lysyl-L-asparaginyl-L-glutamyl-L-glutaminyl- L-glutamyl-L-leucyl-L-leucyl-L-glutamyl-L-leucyl-L-aspartyl-L-lysyl-L-tryptophyl- L-alanyl-L-seryl-L-leucyl-L-tryptophyl-L-asparaginyl-L-tryptophyl-L-phenylalaninamide 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.

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

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.

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.

Pharmacokinetics

Subcutaneous absorption c. 84.3%
Cmax 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.

Enfuvirtide Preparation Products And Raw materials

Raw materials

Preparation Products


Enfuvirtide Suppliers

Global( 124)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Alpha Biopharmaceuticals Co., Ltd
0086-411-39042497
0086-411-39042693 sales@alphabiopharm.com China 921 58
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21676 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Rixing Chemical CO.,LTD
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career henan chemical co
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Chengdu Biopurify Phytochemicals Ltd.
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Chemwill Asia Co.,Ltd.
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Hubei Jusheng Technology Co.,Ltd.
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Hebei Jimi Trading Co., Ltd.
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Hebei Guanlang Biotechnology Co., Ltd.
+8619930501651
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View Lastest Price from Enfuvirtide manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-07-24 Enfuvirtide
159519-65-0
US $20.00 / KG 1KG 98% 20kg career henan chemical co
2019-04-01 Enfuvirtide
159519-65-0
US $1.00 / kg 100g 99.9% 10tons Hebei Jimi Trading Co., Ltd.

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