Zalcitabine

  • CAT Number: A000277
  • CAS Number: 7481-89-2
  • Molecular Formula: C9H13N3O3
  • Molecular Weight: 211.2
  • Purity: ≥95%
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Zalcitabine, also called dideoxycytidine, is a nucleoside analog reverse transcriptase inhibitor (NARTI) 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.

Catalog Number A000277
CAS Number 7481-89-2
Molecular Formula

C9H13N3O3

Purity 95%
Target Reverse Transcriptase
Solubility Soluble in DMSO > 10 mM
Storage -20°C
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 C1CC(OC1CO)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.
<br>

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.

<br>
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.
<br>

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.
<br>

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.
<br>

7: Jin MJ, Han HK. Interaction of zalcitabine with human organic anion
transporter 1. Pharmazie. 2006 May;61(5):491-2. PubMed PMID: 16724555.
<br>

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.
<br>

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.
<br>

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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