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;
ChemSpider	28529638;
UNII	Z4I0C281BJ;
KEGG	D09906;
ChEMBL	ChEMBL2104968;
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 FR, Amador A, Bonaric S, Bot S, Caillet C, et al. (March 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. U.S. National Library of Medicine, U.S. Department of Health and Human Services.
"Fosdevirine". Adis Insight. Springer Nature Switzerland AG. Highest Development Phases: Discontinued, HIV-1 infections
"Fosdevirine". MedKoo Biosciences. GSK2248761 is no longer in clinical development.
Margolis DA, Eron JJ, DeJesus E, White S, Wannamaker P, Stancil B, Johnson M (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 FR, Amador A, Bonaric S, Bot S, Caillet C, et al. (March 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. U.S. National Library of Medicine, U.S. Department of Health and Human Services.

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

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

[5] Margolis DA, Eron JJ, DeJesus E, White S, Wannamaker P, Stancil B, Johnson M (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.