Structure via PubChem · Public domain (PubChem)
zalcitabine
Sign in to saveAlso known as dideoxycytidine (DDC), Hivid®, Ro-242027000/Ro-24-2027-000, 2',3'-Dideoxycytidine, 4-amino-1-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2(1H)-one, Dideoxycytidine, DDCYD, DDC
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.
Chemical data
- Formula
- C9H13N3O3
- Molecular weight
- 211.22 g/mol
- IUPAC name
- 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- SMILES
- C1C[C@@H](O[C@@H]1CO)N2C=CC(=NC2=O)N
- InChIKey
- WREGKURFCTUGRC-POYBYMJQSA-N
- XLogP
- -1.3
- Polar surface area
- 88.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1992
- Admin. routes
- oral
- Indications
- HIV infection, viral disease
via ChEMBL · EBI
Wikidata facts
- Mass
- 211.095691
- Has use
- medication
Show 10 more facts
- found in taxon
- Caenorhabditis elegans
- chemical formula
- C₉H₁₃N₃O₃
- subject has role
- antiviral drug
- medical condition treated
- HIV infection
- isomeric SMILES
- C1C[C@@H](O[C@@H]1CO)N2C=CC(=NC2=O)N
- canonical SMILES
- C1CC(OC1CO)N2C=CC(=NC2=O)N
- World Health Organisation international non-proprietary name
- zalcitabine
- defined daily dose
- 2.25
- Commons category
- Zalcitabine
- melting point
- 218
via Wikidata · CC0
~4 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Drug interactions
- Adverse events
- Resistance
- Pharmacology
- Pharmacokinetics
- Mechanism of action
- History
- References
- Further reading
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.
Excerpted from Wikipedia’s “zalcitabine” article, available under the CC BY-SA 4.0 licence.