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Fosdevirine

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Chemical compound Pharmaceutical compound
Fosdevirine
Clinical data
Other namesGSK2248761; GSK2248761A; IDX-12899; IDX-899
ATC code
  • None
Identifiers
IUPAC name
  • 5-Chloro-3--5-methylphenyl]-methoxyphosphoryl]-1H-indole-2-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC20H17ClN3O3P
Molar mass413.80 g·mol
3D model (JSmol)
SMILES
  • CC1=CC(=CC(=C1)/C=C/C#N)(=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.

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

References

  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. Archived from the original on 2019-08-11. Retrieved 2018-08-14.
  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. S2CID 6147197.
Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)
Capsid inhibitors
Entry/fusion inhibitors
(Discovery and development)
Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))
Maturation inhibitors
Protease Inhibitors (PI)
(Discovery and development)
1 generation
2 generation
Reverse-transcriptase
inhibitors (RTIs)
Nucleoside and
nucleotide (NRTI)
Non-nucleoside (NNRTI)
(Discovery and development)
1 generation
2 generation
Combined formulations
Pharmacokinetic boosters
Experimental agents
Uncoating inhibitors
Transcription inhibitors
Translation inhibitors
BNAbs
Other
Failed agents
°DHHS recommended initial regimen options. Formerly or rarely used agent.
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