Chemistry:Dexelvucitabine

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Dexelvucitabine
Dexelvucitabine.svg
Names
IUPAC name
2′,3′-Didehydro-2′,3′-dideoxy-5-fluorocytidine
Systematic IUPAC name
4-Amino-5-fluoro-1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-1-yl]pyrimidin-2(1H)-one
Other names
Reverset
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
UNII
Properties
C9H10FN3O3
Molar mass 227.195 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Dexelvucitabine is a failed experimental agent for the management of human immunodeficiency virus infection. It is a cytidine nucleoside analog and nucleoside reverse transcriptase inhibitor.[1] that inhibits HIV-1 replication in vitro. During phase II clinical trials there was some indication of a decreased mean viral load in patients with infected human immunodeficiency virus.[2][3]

On April 3, 2006, Pharmasset and Incyte, the pharmaceutical companies developing dexelvucitabine, announced the decision to cease further trials and development of the drug due to an increased incidence of grade 4 hyperlipasemia (an excess of the pancreatic enzyme lipase in the bloodstream) in a phase II trial.[1][4]

References

  1. 1.0 1.1 PubChem. "Dexelvucitabine" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/64973. 
  2. Hernandez-Santiago, Brenda I.; Mathew, Judy S.; Rapp, Kim L.; Grier, Jason P.; Schinazi, Raymond F. (June 2007). "Antiviral and Cellular Metabolism Interactions between Dexelvucitabine and Lamivudine". Antimicrobial Agents and Chemotherapy 51 (6): 2130–2135. doi:10.1128/aac.01543-06. ISSN 0066-4804. PMID 17403996. 
  3. Sobieszczyk, Magdalena E; Talley, Angela K; Wilkin, Timothy; Hammer, Scott M (2005-03-01). "Advances in antiretroviral therapy". Topics in HIV Medicine 13 (1): 24–44. ISSN 2161-5845. PMID 15849370. https://europepmc.org/article/med/15849370. 
  4. Ryder, Neil S (2007-12-01). "Discontinued drugs in 2006: anti-infectives". Expert Opinion on Investigational Drugs 16 (12): 1867–1878. doi:10.1517/13543784.16.12.1867. ISSN 1354-3784. PMID 18041997. https://doi.org/10.1517/13543784.16.12.1867.