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Fosdevirine

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Chemical compound

Pharmaceutical compound

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
PubChemCID	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 thenon-nucleoside reverse transcriptase inhibitor class that was studied for potential use in the treatment ofHIV-AIDS.^[1]^[2]

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

References

[edit]

^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. Archived fromthe original on 2019-08-11. Retrieved2018-08-14.
^"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.S2CID 6147197.

Antiviral drugs:antiretroviral drugs used againstHIV (primarilyJ05)

Capsid inhibitors

Lenacapavir (LEN)

Entry/fusion inhibitors
(Discovery and development)

gp41 (Enfuvirtide (ENF, T-20))^◊
CCR5 (Maraviroc (MVC)
Vicriviroc^†,Cenicriviroc^†,Leronlimab^†)
CD4 (Ibalizumab (IBA),Semzuvolimab^§)
gp120 (Fostemsavir (FTR))

Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))

Maturation inhibitors

Protease Inhibitors (PI)
(Discovery and development)

1^st generation	Amprenavir (APV)^‡ Fosamprenavir (FPV) Indinavir (IDV)^◊ Lopinavir (LPV) Nelfinavir (NFV)^◊ Ritonavir (RTV)^# Saquinavir (SQV)^◊
2^nd generation	Atazanavir (ATV)°^# Darunavir (DRV)°^# Tipranavir (TPV)^◊ TMC-310911^§

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside and
nucleotide (NRTI)

Nucleoside analogues/NRTIs:Abacavir (ABC)^#
Didanosine (ddI)^◊
Emtricitabine (FTC)
Lamivudine (3TC)^#
Stavudine (d4T)^◊
Zalcitabine (ddC)^‡
Zidovudine (AZT, ZDV)^#
Amdoxovir^†
Apricitabine^†
Censavudine^†
Elvucitabine^†
Islatravir (EFdA, ISL)^§
Racivir^†
Stampidine^†

Non-nucleoside (NNRTI)
(Discovery and development)

1^st generation	Efavirenz (EFV)^# Nevirapine (NVP)^# Delavirdine (DLV)^‡
2^nd generation	diarylpyrimidines Dapivirine (DPV) Etravirine (ETR) Rilpivirine (RPV) Doravirine (DOR) Elsulfavirine (ESV)

Combined formulations

Pharmacokinetic boosters

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)
Transcription inhibitors	Tat antagonists
Translation inhibitors	Trichosanthin
BNAbs	Elipovimab
Other	Abzyme BIT225^† Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Fosdevirine^† Griffithsin Hydroxycarbamide KP-1461^† Miltefosine Portmanteau inhibitors Scytovirin Seliciclib^† Synergistic enhancers Tre recombinase Zinc finger protein transcription factor
Failed agents	Aplaviroc Atevirdine Brecanavir Capravirine Dexelvucitabine Droxinavir Lasinavir Emivirine Lersivirine Lodenosine Loviride Mozenavir Palinavir Telinavir

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

°DHHSrecommendedinitial regimen options.^◊Formerly or rarely used agent.

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