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Dexelvucitabine

From Wikipedia, the free encyclopedia
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 mass227.195 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Dexelvucitabine is a failed experimental agent for the management ofhuman immunodeficiency virus infection. It is acytidine nucleoside analog and nucleosidereverse transcriptase inhibitor.[1] that inhibits HIV-1 replication in vitro. Duringphase 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 andIncyte, 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 enzymelipase in the bloodstream) in a phase II trial.[1][4]

References

[edit]
  1. ^abPubChem."Dexelvucitabine".pubchem.ncbi.nlm.nih.gov. Retrieved2022-04-07.
  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.


Capsid inhibitors
Entry/fusion inhibitors
(Discovery and development)
Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))
Maturation inhibitors
Protease Inhibitors (PI)
(Discovery and development)
1st generation
2nd generation
Reverse-transcriptase
inhibitors
(RTIs)
Nucleoside and
nucleotide (NRTI)
Non-nucleoside (NNRTI)
(Discovery and development)
1st generation
2nd generation
Combined formulations
Pharmacokinetic boosters
Experimental agents
Uncoating inhibitors
Transcription inhibitors
Translation inhibitors
BNAbs
Other
Failed agents
°DHHSrecommendedinitial regimen options.Formerly or rarely used agent.


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