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Dexelvucitabine

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Dexelvucitabine
Names
IUPAC name 2′,3′-Didehydro-2′,3′-dideoxy-5-fluorocytidine
Systematic IUPAC name 4-Amino-5-fluoro-1-pyrimidin-2(1H)-one
Other names Reverset
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: HSBKFSPNDWWPSL-CAHLUQPWSA-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/s1Key: HSBKFSPNDWWPSL-CAHLUQPWBD
SMILES
  • F\C1=C\N(C(=O)\N=C1\N)/2O(\C=C\2)CO
Properties
Chemical formula C9H10FN3O3
Molar mass 227.195 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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. 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.

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.

References

  1. ^ 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.


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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