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Zalcitabine information


Zalcitabine
Clinical data
Trade namesHivid (discontinued)
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: D
Routes of
administration
Oral
ATC code
  • J05AF03 (WHO)
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability>80%
Protein binding<4%
MetabolismHepatic
Elimination half-life2 hours
ExcretionRenal (circa 80%)
Identifiers
IUPAC name
  • 4-amino-1-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
CAS Number
  • 7481-89-2 checkY
PubChem CID
  • 24066
IUPHAR/BPS
  • 4828
DrugBank
  • DB00943 checkY
ChemSpider
  • 22498 checkY
UNII
  • 6L3XT8CB3I
KEGG
  • D00412 checkY
ChEBI
  • CHEBI:10101 checkY
ChEMBL
  • ChEMBL853 checkY
NIAID ChemDB
  • 000006
CompTox Dashboard (EPA)
  • DTXSID0023747 Edit this at Wikidata
ECHA InfoCard100.149.677 Edit this at Wikidata
Chemical and physical data
FormulaC9H13N3O3
Molar mass211.221 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H](CC2)CO
InChI
  • InChI=1S/C9H13N3O3/c10-7-3-4-12(9(14)11-7)8-2-1-6(5-13)15-8/h3-4,6,8,13H,1-2,5H2,(H2,10,11,14)/t6-,8+/m0/s1 checkY
  • Key:WREGKURFCTUGRC-POYBYMJQSA-N checkY
  (verify)

Zalcitabine (2′-3′-dideoxycytidine, ddC), also called dideoxycytidine, is a nucleoside analog reverse-transcriptase inhibitor (NRTI) sold under the trade name Hivid. Zalcitabine was the third antiretroviral to be approved by the Food and Drug Administration (FDA) for the treatment of HIV/AIDS. It is used as part of a combination regimen.

Zalcitabine appears less potent than some other nucleoside RTIs, has an inconvenient three-times daily frequency and is associated with serious adverse events. For these reasons it is now rarely used to treat human immunodeficiency virus (HIV), and it has even been removed from pharmacies entirely in some countries.[1]

  1. ^ "zalcitabine (CHEBI:10101)". www.ebi.ac.uk. Retrieved 2021-01-18.

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Nucleoside analogue

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antacids can increase pH and inhibit the absorption of other drugs such as zalcitabine, tipranavir and amprenavir. The opposite is more common, with, for example...

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Jerome Horwitz

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ATC code J05

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Hiroaki Mitsuya

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Dihydrolevoglucosenone

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acid produces optically pure 5-hydroxymethyldihydrofuranone, from which zalcitabine, formerly a HIV drug, is available. In a two-step hydrogenation process...

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Samuel Broder

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AIDS epidemic, he co-developed zidovudine (AZT), didanosine (ddI), and zalcitabine (ddC), which were the first effective drugs licensed for the treatment...

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Jacques Leibowitch

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with advanced HIV-1 infection treated with ritonavir, zidovudine and zalcitabine triple therapy". Antivir Ther. 2 (3): 175–83. PMID 11322272. En savoir...

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It also transports the anti-viral nucleoside analogues Zidovudine and Zalcitabine. Che M, Ortiz DF, Arias IM (Jun 1995). "Primary structure and functional...

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nucleoside analogs acyclovir (ACV), zidovudine (AZT), didanosine (ddI), zalcitabine (ddC), lamivudine (3TC), stavudine (d4T), trifluridine, cidofovir, adefovir...

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