3582. Enfuvirtide

Nomenclature

CAS number: 159519-65-0
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; pentafuside; DP-178; T-20; Fuzeon (Roche).
C204H301N51O64; mol wt 4491.88.
C 54.55%, H 6.75%, N 15.90%, O 22.80%.

Description and references

HIV fusion inhibitor. Synthetic, 36 amino acid peptide corresponding to a region of gp41, the transmembrane subunit of the HIV-1 envelope protein. Prepn and biological activity: D. P. Bolognesi et al., WO 9428920; eidem, US 5464933 (1994, 1995 both to Duke Univ.); C. T. Wild et al., Proc. Natl. Acad. Sci. USA 91, 9770 (1994). Mechanism of action study: R. A. Furuta et al., Nat. Struct. Biol. 5, 276 (1998). Clinical pharmacokinetics: J. M. Kilby et al., AIDS Res. Hum. Retroviruses 18, 685 (2002). Clinical trial in drug-resistant HIV-1: J. P. Lalezari et al., N. Engl. J. Med. 348, 2175 (2003); A. Lazzarin et al., ibid. 2186. Review of development and clinical experience: A. Lazzarin, Expert Opin. Pharmacother. 6, 453-464 (2005).

Properties

White to off-white amorphous solid. Negligible soly in pure water. Soly increases in aq buffers (pH 7.5) to 85-142 g/100 ml.

Therapeutic Category

Antiretroviral.

Keywords

HIV Fusion Inhibitor; Antiretroviral; Fusion Inhibitors