Zalcitabine

For research use only. Not for therapeutic Use.

  • CAT Number: A000277
  • CAS Number: 7481-89-2
  • Molecular Formula: C9H13N3O3
  • Molecular Weight: 211.20
  • Purity: ≥95%
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Zalcitabine(Cat No.:A000277)is a nucleoside reverse transcriptase inhibitor (NRTI) used in the treatment of HIV infection. It works by incorporating into viral DNA during replication, causing premature termination and inhibiting viral replication. Zalcitabine is typically used as part of combination antiretroviral therapy to reduce the viral load and enhance immune function in HIV patients. While effective, its use has declined due to the availability of newer drugs with improved safety profiles, as Zalcitabine is associated with side effects such as peripheral neuropathy and pancreatitis. It remains a key compound in historical HIV therapy research.


Catalog Number A000277
CAS Number 7481-89-2
Synonyms

2/’,3/’-DIDEOXYCYTIDINE; 7481-89-2; Dideoxycytidine; DdCyd; HIVID

Molecular Formula C9H13N3O3
Purity ≥95%
Target HIV
Solubility Soluble in DMSO > 10 mM
Storage -20°C
IUPAC Name 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
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
InChIKey WREGKURFCTUGRC-POYBYMJQSA-N
SMILES C1C[C@@H](O[C@@H]1CO)N2C=CC(=NC2=O)N
Reference

1: Vasilyeva SV, Shtil AA, Petrova AS, Balakhnin SM, Achigecheva PY, Stetsenko
DA, Silnikov VN. Conjugates of phosphorylated zalcitabine and lamivudine with
SiO(2) nanoparticles: Synthesis by CuAAC click chemistry and preliminary
assessment of anti-HIV and antiproliferative activity. Bioorg Med Chem. 2017 Mar
1;25(5):1696-1702. doi: 10.1016/j.bmc.2017.01.038. Epub 2017 Jan 25. PubMed PMID:
28169081.
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2: Martins FT, Guimar&#227;es FF, Honorato SB, Ayala AP, Ellena J. Vibrational and
thermal analyses of multicomponent crystal forms of the anti-HIV drugs lamivudine
and zalcitabine. J Pharm Biomed Anal. 2015 Jun 10;110:76-82. doi:
10.1016/j.jpba.2015.03.004. Epub 2015 Mar 11. PubMed PMID: 25808817.
<br>

3: Leandro KC, Moreira JC, Farias PA. Determination of Zalcitabine in Medicaments
by Differential Pulse Voltammetry. J Pharm (Cairo). 2013;2013:495814. doi:
10.1155/2013/495814. Epub 2013 Apr 4. PubMed PMID: 26555981; PubMed Central
PMCID: PMC4590814.

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4: Gerber M, Breytenbach JC, du Plessis J. Transdermal penetration of
zalcitabine, lamivudine and synthesised N-acyl lamivudine esters. Int J Pharm.
2008 Mar 3;351(1-2):186-93. Epub 2007 Oct 6. PubMed PMID: 18006257.
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5: Hanes JW, Johnson KA. Exonuclease removal of dideoxycytidine (zalcitabine) by
the human mitochondrial DNA polymerase. Antimicrob Agents Chemother. 2008
Jan;52(1):253-8. Epub 2007 Nov 5. PubMed PMID: 17984232; PubMed Central PMCID:
PMC2223897.
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6: Lebrecht D, Vargas-Infante YA, Setzer B, Kirschner J, Walker UA. Uridine
supplementation antagonizes zalcitabine-induced microvesicular steatohepatitis in
mice. Hepatology. 2007 Jan;45(1):72-9. PubMed PMID: 17187420.
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7: Jin MJ, Han HK. Interaction of zalcitabine with human organic anion
transporter 1. Pharmazie. 2006 May;61(5):491-2. PubMed PMID: 16724555.
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8: Oh YH, Han HK. Altered pharmacokinetics of zalcitabine by concurrent use of
NSAIDs in rats. Acta Pharmacol Sin. 2006 Jan;27(1):119-22. PubMed PMID: 16364218.
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9: Sangkitporn S, Shide L, Klinbuayaem V, Leenasirimakul P, Wirayutwatthana NA,
Leechanachai P, Dettrairat S, Kunachiwa W, Thamlikitkul V. Efficacy and safety of
zidovudine and zalcitabine combined with a combination of herbs in the treatment
of HIV-infected Thai patients. Southeast Asian J Trop Med Public Health. 2005
May;36(3):704-8. PubMed PMID: 16124442.
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10: Moyle G. A re-evaluation of zalcitabine. Expert Opin Investig Drugs. 1998
Mar;7(3):451-62. PubMed PMID: 15991985.

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