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]

Dexelvucitabine
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
  • InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7 /m0/s1 ☒N
    Key: HSBKFSPNDWWPSL-CAHLUQPWSA-N ☒N
  • InChI=1/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7 /m0/s1
    Key: HSBKFSPNDWWPSL-CAHLUQPWBD
  • F\C1=C\N(C(=O)\N=C1\N)[C@@H]/2O[C@@H](\C=C\2)CO
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).
☒N verify (what is checkY☒N ?)

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

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  1. ^ a b PubChem. "Dexelvucitabine". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-07.
  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. PMC 1891415. PMID 17403996.2130-2135&rft.date=2007-06&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1891415#id-name=PMC&rft.issn=0066-4804&rft_id=info:pmid/17403996&rft_id=info:doi/10.1128/aac.01543-06&rft.aulast=Hernandez-Santiago&rft.aufirst=Brenda I.&rft.au=Mathew, Judy S.&rft.au=Rapp, Kim L.&rft.au=Grier, Jason P.&rft.au=Schinazi, Raymond F.&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1891415&rfr_id=info:sid/en.wikipedia.org:Dexelvucitabine" class="Z3988">
  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 15849370.24-44&rft.date=2005-03-01&rft_id=info:pmid/15849370&rft.issn=2161-5845&rft.aulast=Sobieszczyk&rft.aufirst=Magdalena E&rft.au=Talley, Angela K&rft.au=Wilkin, Timothy&rft.au=Hammer, Scott M&rft_id=https://europepmc.org/article/med/15849370&rfr_id=info:sid/en.wikipedia.org:Dexelvucitabine" class="Z3988">
  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. S2CID 40129603.1867-1878&rft.date=2007-12-01&rft.issn=1354-3784&rft_id=https://api.semanticscholar.org/CorpusID:40129603#id-name=S2CID&rft_id=info:pmid/18041997&rft_id=info:doi/10.1517/13543784.16.12.1867&rft.aulast=Ryder&rft.aufirst=Neil S&rft_id=https://doi.org/10.1517/13543784.16.12.1867&rfr_id=info:sid/en.wikipedia.org:Dexelvucitabine" class="Z3988">