Fosdevirine

Fosdevirine
Clinical data
Other names	GSK2248761; GSK2248761A; IDX-12899; IDX-899
ATC code	None;
Identifiers
	IUPAC name 5-Chloro-3-[[3-[(E)-2-cyanoethenyl]-5-methylphenyl]-methoxyphosphoryl]-1H-indole-2-carboxamide;
CAS Number	1018450-26-4;
PubChem CID	44232529;
UNII	Z4I0C281BJ;
Chemical and physical data
Formula	C20H17ClN3O3P
Molar mass	413.80 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=CC(=C1)/C=C/C#N)[P@](=O)(C2=C(NC3=C2C=C(C=C3)Cl)C(=O)N)OC;
	InChI InChI=1S/C20H17ClN3O3P/c1-12-8-13(4-3-7-22)10-15(9-12)28(26,27-2)19-16-11-14(21)5-6-17(16)24-18(19)20(23)25/h3-6,8-11,24H,1-2H3,(H2,23,25)/b4-3+/t28-/m1/s1; Key:CGBYTKOSZYQOPV-ASSBYYIWSA-N;

Fosdevirine is an experimental antiviral agent of the non-nucleoside reverse transcriptase inhibitor class that was studied for potential use in the treatment of HIV-AIDS.[1][2]

It was discovered by Idenix Pharmaceuticals and was being developed by GlaxoSmithKline and ViiV Healthcare, but it has now been discontinued[3][4] due to unexpected side effects.[5]

References

Dousson, C; Alexandre, F. R; Amador, A; Bonaric, S; Bot, S; Caillet, C; Convard, T; Da Costa, D; Lioure, M. P; Roland, A; Rosinovsky, E; Maldonado, S; Parsy, C; Trochet, C; Storer, R; Stewart, A; Wang, J; Mayes, B. A; Musiu, C; Poddesu, B; Vargiu, L; Liuzzi, M; Moussa, A; Jakubik, J; Hubbard, L; Seifer, M; Standring, D (2016). "Discovery of the Aryl-phospho-indole IDX899, a Highly Potent Anti-HIV Non-nucleoside Reverse Transcriptase Inhibitor". Journal of Medicinal Chemistry. 59 (5): 1891–8. doi:10.1021/acs.jmedchem.5b01430. PMID 26804933.
"Fosdevirine". aidsinfo.nih.gov.
"Fosdevirine". Adis Insight. Highest Development Phases: Discontinued, HIV-1 infections
"Fosdevirine". MedKoo Biosciences. GSK2248761 is no longer in clinical development.
Margolis, David A; Eron, Joseph; Dejesus, Edwin; White, Scott; Wannamaker, Paul; Stancil, Britt; Johnson, Mark (2013). "Unexpected finding of delayed-onset seizures in HIV-positive, treatment-experienced subjects in the phase IIb evaluation of fosdevirine (GSK2248761)". Antiviral Therapy. 19 (1): 69–78. doi:10.3851/IMP2689. PMID 24158593.

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[1] Dousson, C; Alexandre, F. R; Amador, A; Bonaric, S; Bot, S; Caillet, C; Convard, T; Da Costa, D; Lioure, M. P; Roland, A; Rosinovsky, E; Maldonado, S; Parsy, C; Trochet, C; Storer, R; Stewart, A; Wang, J; Mayes, B. A; Musiu, C; Poddesu, B; Vargiu, L; Liuzzi, M; Moussa, A; Jakubik, J; Hubbard, L; Seifer, M; Standring, D (2016). "Discovery of the Aryl-phospho-indole IDX899, a Highly Potent Anti-HIV Non-nucleoside Reverse Transcriptase Inhibitor". Journal of Medicinal Chemistry. 59 (5): 1891–8. doi:10.1021/acs.jmedchem.5b01430. PMID 26804933.

[2] "Fosdevirine". aidsinfo.nih.gov.

[3] "Fosdevirine". Adis Insight. Highest Development Phases: Discontinued, HIV-1 infections

[4] "Fosdevirine". MedKoo Biosciences. GSK2248761 is no longer in clinical development.

[5] Margolis, David A; Eron, Joseph; Dejesus, Edwin; White, Scott; Wannamaker, Paul; Stancil, Britt; Johnson, Mark (2013). "Unexpected finding of delayed-onset seizures in HIV-positive, treatment-experienced subjects in the phase IIb evaluation of fosdevirine (GSK2248761)". Antiviral Therapy. 19 (1): 69–78. doi:10.3851/IMP2689. PMID 24158593.