Product Name

Zalcitabine

CAS Number

7481-89-2

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Product Name:
Zalcitabine
CAS Number:
7481-89-2
Indication:
For the treatment of Human immunovirus (HIV) infections in conjunction with other antivirals.
Mode of Action:

Zalcitabine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Within cells, zalcitabine is converted to its active metabolite, dideoxycytidine 5'-triphosphate (ddCTP), by the sequential action of cellular enzymes. ddCTP interferes with viral RNA-directed DNA polymerase (reverse transcriptase) by competing for utilization of the natural substrate deoxycytidine 5'-triphosphate (dCTP), as well as incorpating into viral DNA. Due to it's lack of a 3'-OH group, the formation of a 5' to 3' phosphodiester linkage that is necessary for DNA chain elongation is inhibited, thus leading to the termination of viral DNA growth.

Pharmacodynamics:

Zalcitabine is an analog of 2'-deoxycytidine that is pharmacologically related to but structurally different from other nucleotide reverse transcriptase inhibitors (NRTIs). Zalcitabine inhibits the activity of HIV-1 reverse transcriptase (RT) both by competing with the natural substrate dGTP and by its incorporation into viral DNA.

Metabolism:

Hepatic

Toxicity:

Acute overdose: Inadvertent pediatric overdoses have occurred with doses up to 1.5 mg/kg zalcitabine. Chronic overdose: in an initial dose-finding study in which zalcitabine was administered at doses 25 times (0.25 mg/kg every 8 hours) the currently recommended dose, one patient discontinued zalcitabine after 1_ weeks of treatment subsequent to the development of a rash and fever.

IUPAC:
4-amino-1-[(2R, 5S)-5-(hydroxymethyl)oxolan-2-yl]-1, 2-dihydropyrimidin-2-one
ATC:
J05AF03
PubChem:
24066
DrugBank:
DB00943 (APRD00562)
Formula:
C17H15N5O
Molecular Mass:
211.2178
Synonyms:
DDC DDCYD Dideoxycytidine
SMILES:
NC1=NC(=O)N(C=C1)[C@H]1CC[C@@H](CO)O1
InChi:
WREGKURFCTUGRC-POYBYMJQSA-N
General Reference:
General Reference:

  1. Shelton MJ, OêDonnell AM, Morse GD: Zalcitabine. Ann Pharmacother. 1993 Apr;27(4):480-9. Pubmed
  2. Devineni D, Gallo JM: Zalcitabine. Clinical pharmacokinetics and efficacy. Clin Pharmacokinet. 1995 May;28(5):351-60. Pubmed 7614775

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