Dexelvucitabine

Last updated
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
PubChem CID
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 X mark.svgN
    Key: HSBKFSPNDWWPSL-CAHLUQPWSA-N X mark.svgN
  • 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).
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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 2 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.
  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.
  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.



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