ENFUVIRTIDE

ENFUVIRTIDE

Synonyms. Enfuvirtide; Fuzeon; N-Acetyl-L-tyrosyl-L-threonyl-L- seryl-L-leucyl-L-isoleucyl- L-histadyl-L- seryl-L -leucyl- L- isoleucyl-L-alpha-glutamyl-L- alpha-glutamyl-L-seryl-L-glutaminyl-L- asparaginyl -L- glutaminyl- L-glutaminyl-L-alpha-glutamyl-L-lysyl-L- asparaginyl-L-alpha-glutamyl -L-glutaminyl- L-alpha-glutamyl- L-leucyl-L-leucyl-L-alpha-glutamyl-L-leucyl-L-alpha- aspartyl- L-lysyl-L- tryptophyl-L- alanyl-L-seryl-L-leucyl-L- tryptophyl-L -asparaginyl-L-tryptophyl-L- phenylalaninamide; Pentafuside; T 20 (peptide); CH3CO-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 Other RN: 262434-79-7

PRODUCT IDENTIFICATION
CAS RN	159519-65-0
EINECS RN
FORMULA	C₂₀₄H₃₀₁N₅₁O₆₄
MOLE WEIGHT	4491.90
H.S CODE
SMILES	CC[C@H](C)[C@@H](C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H] (CCC (=O )O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(=O)N)C (=O)N[C@@H] (CC(=O)N)C(=O)N[C@@H](CCC(=O)N)C (=O)N[C@@H](CCC(=O)N) C(=O) N[C@@H](CCC(=O)O)C (=O)N[C@@H](CCCCN)C (=O)N[C @@H](CC(= O)N) C(=O)N [C@@H](CCC(=O)O)C(=O)N[C@@H] (CCC(=O)N)C (=O)N[ C@@ H](CCC(=O)O) C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C) C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H] (CC(C)C)C(=O)N [C@@H](C C(= O)O)C(=O) N[C@@H](CCCCN)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2) C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C (=O)N[C@@H](CC(C)C)C (=O)N[ C@@H](Cc3c[nH]c4c3ccc c4)C(=O)N[C@@H](CC(=O)N)C(=O )N[C@@H] (Cc5c[nH]c6c5 cccc6)C(=O)N[C@@H](Cc7ccccc7)C(=O)N)NC(=O )[C @H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](Cc8cnc[nH]8)NC(= O)[C @H]([C@@H](C)CC)NC(=O)[C@H](CC (C)C)NC(=O)[C@H](CO)NC (=O)[ C@H]([C@@H] (C)O)NC(=O)[C@H](Cc9ccc(cc9)O)NC(=O)C;
CLASSIFICATION	Anti-HIV, Anti-Infective, Anti-Retroviral, Antiviral, HIV Fusion Inhibitor
EXTRA NOTES	Corresponds to the heptad repeat sequence of HIV-1 gp41. Enfuvirtide is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV infection in adults and children 6 years of age and older. Enfuvirtide is for people who have not responded well enough to treatment with other anti-HIV medicines. Enfuvirtide is always used in combination with other anti-HIV medicines.

PHYSICAL AND CHEMICAL PROPERTIES
PHYSICAL STATE.	powder
MELTING POINT
BOILING POINT
DENSITY
SOLUBILITY IN WATER
SOLVENT SOLUBILITY
VAPOR DENSITY
log P(octanol-water)
VAPOR PRESSURE
AUTOIGNITION TEMP
pH
REFRACTIVE INDEX
FLASH POINT

STABILITY AND REACTIVITY
STABILITY	Stable under normal conditions.
INCOMPATIBLE MATERIALS	Strong oxidizing agents
POLYMERIZATION	Has not been reported
NFPA RATINGS	Health: 2,Flammability:1, Reactivity: 0

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Enfuvirtide

Google Scholar Search - Enfuvirtide

Drug Information Portal (U.S. National Library of Medicine) - Enfuvirtide

PubChem Compound Summary - Enfuvirtide

Drug Bank - Enfuvirtide

KEGG (Kyoto Encyclopedia of Genes and Genomes) - Enfuvirtide

http://www.ebi.ac.uk/ - Enfuvirtide

http://www.ncbi.nlm.nih.gov/ - Enfuvirtide

http://aidsinfo.nih.gov/
Enfuvirtide is a prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of HIV infection in adults and children 6 years of age and older. Enfuvirtide is for people who have not responded well enough to treatment with other anti-HIV medicines. Enfuvirtide is always used in combination with other anti-HIV medicines. Enfuvirtide is a type of anti-HIV medicine called a fusion inhibitor. Fusion inhibitors work by blocking HIV’s ability to merge with and infect healthy cells. When used with other anti-HIV medicines, enfuvirtide may lower the amount of HIV in the blood. Enfuvirtide does not cure HIV/AIDS. It is not known if enfuvirtide reduces the risk of passing HIV to other people.

http://www.antimicrobe.org/
Mechanism of Action: Enfuvirtide binds to a region of the gp41 subunit of the HIV-1 envelope glycoprotein (first heptad repeat domain – HR1), that mediates a conformational change required for viral and host-cell membrane fusion. This conformational change is essential to bring the viral and cellular membranes into close enough proximity for fusion and subsequent viral entry into the host-cell. Enfuvirtide prevents this step and thus also the infection of the cell by HIV-1.

http://www.plosone.org/
Since the first appearance of enfuvirtide, the search for peptide drugs against HIV has been a growing field of research and several candidates proved to be efficient in vitro. As our knowledge of HIV structure and function progresses, more sophisticated peptide designs are developed in order to overcome viral resistance to previous drugs. The initial view of the mechanism of action of these peptides, that is, binding to NHR region and block 6-helix bundle formation, has been refined over the years. Other factors besides gp41-peptide binding can contribute to explain the mode of action of these peptides. In fact enfuvirtide does not form stable 6-helix bundle structures with N36, a NHR derived peptide, contrary to C34, another CHR derived peptide. Moreover, peptides derived from the membrane-spanning domain in gp41 and the co-receptor binding site in gp120 inhibited enfuvirtide antiviral activity, meaning that other sites in the viral envelope could be targeted by enfuvirtide.

SALES SPECIFICATION
APPEARANCE	white powder
ASSAY	95.0~105.0% (on Anhydrous, Acetic Acid free basis)
WATER	5.0% max (Karl Fischer)
ACETATE CONTENT	10.0% max (HPLC)
AMINO ACID COMPOSITION	±15% theoretical
INDIVIDUAL IMPURITY	1.0% max (HPLC)
PEPTIDE CONTENT	80% min (by %N)
BACTERIAL ENDOTOXINS	5EU/mg max

TRANSPORT & REGULATORY INFORMATION
UN NO.	Not known
HAZARD CLASS
PACKING GROUP

SAFETY INFORMATION
HAZARD OVERVIEW	Avoid contact and inhalation. May causes eye irritation. May causes skin irritation. May cause gastrointestinal irritation. May causes respiratory tract irritation
HAZARD CODES
RISK PHRASES
SAFETY PHRASES	22-24/25

PACKING