Fosdevirine

{{Short description|Chemical compound}}

{{Infobox drug

| drug_name =

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| IUPAC_name = 5-Chloro-3-[[3-[(E)-2-cyanoethenyl]-5-methylphenyl]-methoxyphosphoryl]-1H-indole-2-carboxamide

| image = Fosdevirine.svg

| width = 180

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| CAS_number = 1018450-26-4

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| ATC_prefix = None

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| PubChem = 44232529

| DrugBank =

| ChemSpiderID = 28529638

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z4I0C281BJ

| KEGG = D09906

| ChEBI =

| ChEMBL = 2104968

| synonyms = GSK2248761; GSK2248761A; IDX-12899; IDX-899

| C=20|H=17|Cl=1|N=3|O=3|P=1

| smiles = CC1=CC(=CC(=C1)/C=C/C#N)[P@](=O)(C2=C(NC3=C2C=C(C=C3)Cl)C(=O)N)OC

| StdInChI=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

| StdInChIKey=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.{{cite journal | vauthors = Dousson C, Alexandre FR, Amador A, Bonaric S, Bot S, Caillet C, Convard T, da Costa D, Lioure MP, Roland A, Rosinovsky E, Maldonado S, Parsy C, Trochet C, Storer R, Stewart A, Wang J, Mayes BA, Musiu C, Poddesu B, Vargiu L, Liuzzi M, Moussa A, Jakubik J, Hubbard L, Seifer M, Standring D | display-authors = 6 | title = Discovery of the Aryl-phospho-indole IDX899, a Highly Potent Anti-HIV Non-nucleoside Reverse Transcriptase Inhibitor | journal = Journal of Medicinal Chemistry | volume = 59 | issue = 5 | pages = 1891–8 | date = March 2016 | pmid = 26804933 | doi = 10.1021/acs.jmedchem.5b01430 }}{{Cite web | url = https://aidsinfo.nih.gov/drugs/552/fosdevirine/0/professional | title = Fosdevirine | work = AIDSinfo | publisher = U.S. National Library of Medicine, U.S. Department of Health and Human Services | access-date = 2018-08-14 | archive-date = 2019-08-11 | archive-url = https://web.archive.org/web/20190811180837/https://aidsinfo.nih.gov/drugs/552/fosdevirine/0/professional | url-status = dead }}

It was discovered by Idenix Pharmaceuticals and was being developed by GlaxoSmithKline and ViiV Healthcare, but it has now been discontinued{{cite web | url = https://adisinsight.springer.com/drugs/800027243 | title = Fosdevirine | work = Adis Insight | publisher = Springer Nature Switzerland AG | quote = Highest Development Phases: Discontinued, HIV-1 infections}}{{Cite web | url = https://www.medkoo.com/products/7914 | title = Fosdevirine | publisher = MedKoo Biosciences | quote = GSK2248761 is no longer in clinical development.}} due to unexpected side effects.{{cite journal | vauthors = Margolis DA, Eron JJ, DeJesus E, White S, Wannamaker P, Stancil B, Johnson M | title = Unexpected finding of delayed-onset seizures in HIV-positive, treatment-experienced subjects in the Phase IIb evaluation of fosdevirine (GSK2248761) | journal = Antiviral Therapy | volume = 19 | issue = 1 | pages = 69–78 | year = 2013 | pmid = 24158593 | doi = 10.3851/IMP2689 | s2cid = 6147197 | doi-access = free }}