Zalcitabine

CAS# 7481-89-2

Zalcitabine

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Chemical structure

Zalcitabine

3D structure

Chemical Properties of Zalcitabine

Cas No. 7481-89-2 SDF Download SDF
PubChem ID 24066 Appearance Powder
Formula C9H13N3O3 M.Wt 211.22
Type of Compound N/A Storage Desiccate at -20°C
Synonyms ddC; Dideoxycytidine; 2',3'-Dideoxycytidine
Solubility DMSO : 16.67 mg/mL (78.92 mM; Need ultrasonic and warming)
Chemical Name 4-amino-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
SMILES C1CC(OC1CO)N2C=CC(=NC2=O)N
Standard InChIKey WREGKURFCTUGRC-POYBYMJQSA-N
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Zalcitabine

DescriptionZalcitabine is a potent nucleoside analogue reverse transcriptase inhibitor used in the treatment of HIV infection.In Vitro:Zalcitabine is a dideoxynucleoside antiretroviral agent that is phosphorylated to the active metabolite 2',3'-dideoxycytidine 5'-triphosphate (ddCTP) within both uninfected and HIV-infected cells. At therapeutic concentrations, ddCTP inhibits HIV replication by inhibiting the enzyme reverse transcriptase and terminating elongation of the proviral DNA chain[1]. Zalcitabine exhibits the inhibition effect on the cellular uptake of [3H]-PAH in CHO/hOAT1 cells with an IC50 value of 1.23 mM. Furthermore, the cellular uptake of zalcitabine increased threefold with the enhancement of hOATI activity in CHO/hOAT1 cells[2].

References:
[1]. Adkins JC, et al. Zalcitabine. An update of its pharmacodynamic and pharmacokinetic properties and clinical efficacy in the management of HIV infection.Drugs. 1997 Jun;53(6):1054-80. [2]. Jin MJ, et al. Interaction of zalcitabine with human organic anion transporter 1. Pharmazie. 2006 May;61(5):491-2.

Zalcitabine Dilution Calculator

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Zalcitabine Molarity Calculator

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Preparing Stock Solutions of Zalcitabine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.7344 mL 23.672 mL 47.344 mL 94.688 mL 118.36 mL
5 mM 0.9469 mL 4.7344 mL 9.4688 mL 18.9376 mL 23.672 mL
10 mM 0.4734 mL 2.3672 mL 4.7344 mL 9.4688 mL 11.836 mL
50 mM 0.0947 mL 0.4734 mL 0.9469 mL 1.8938 mL 2.3672 mL
100 mM 0.0473 mL 0.2367 mL 0.4734 mL 0.9469 mL 1.1836 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Zalcitabine

Zalcitabine is a nucleoside analog reverse transcriptase inhibitor (NRTI).

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References on Zalcitabine

Transdermal penetration of zalcitabine, lamivudine and synthesised N-acyl lamivudine esters.[Pubmed:18006257]

Int J Pharm. 2008 Mar 3;351(1-2):186-93.

The objective of this study was to determine the in vitro transdermal permeation through human epidermis of Zalcitabine, lamivudine and the synthesised N-acyl lamivudine esters, with and without the use of Pheroid as delivery system and to establish a correlation, if any, with selected physicochemical properties. Six N-acyl lamivudine esters were prepared by acylation of lamivudine with six different acid chlorides. The experimental aqueous solubility, log D and in vitro transdermal flux values were determined for these compounds. There was an inverse correlation between the aqueous solubility and the log D values. The median flux of Zalcitabine (0.442 micromol/cm2 h) in PBS was lower than that of lamivudine (4.289 micromol/cm2 h), but in Pheroid, lamivudine (0.011 micromol/cm2 h) had a slightly lower median flux than Zalcitabine (0.015 micromol/cm2 h). Entrapment of compounds in Pheroid was confirmed by confocal laser scanning microscopy.

Vibrational and thermal analyses of multicomponent crystal forms of the anti-HIV drugs lamivudine and zalcitabine.[Pubmed:25808817]

J Pharm Biomed Anal. 2015 Jun 10;110:76-82.

The vibrational and thermal characterizations of four multicomponent molecular crystals of lamivudine, namely, lamivudine hydrochloride anhydrate (1), lamivudine hydrochloride monohydrate (2), lamivudine duplex I (3), with a 8:2:2:1:4 lamivudine:maleic acid:HCl:(CH3)2CHOH:H2O stoichiometry, being all three more soluble in water than the commercial solid form of lamivudine, and lamivudine maleate (4), have been performed here by infrared (IR) and Raman spectroscopy, differential scanning calorimetry (DSC), and thermogravimetry (TG). Furthermore, the vibrational spectra of Zalcitabine hydrochloride (5), isostructural to 1 but with a methylene moiety in the 3'-position of the five-membered ring instead of sulfur in lamivudine, have also been measured in order to point out the role of this molecular substitution and conformation in the vibrational modes of the salts. In fact, scattering bands at the high frequency range relative to CH stretching modes are not superimposable in the Raman spectra of 1 and 5, even though these crystal forms are assembled with the same molecular conformation and intermolecular packing. At the same time, the structural similarity between 1 and 5 can be reflected in their IR spectra, as in the carbonyl and iminium stretching bands shifted to lower frequencies as consequence of their hydrogen bonding engagement. Furthermore, a scattering band at 3057 cm(-1) is observed only in the Raman spectra of crystal forms present with their 5'-CH2OH moiety in-gauche conformation, namely, 2-4. It is absent in the Raman spectra of 1 and 5 whose 5'-CH2OH moiety adopts (+)gauche conformation. In-gauche conformation, the 5'-OH oxygen is pointed toward one of the two aromatic CH hydrogens. Consequently, there is formation of an intramolecular hydrogen bond between them, shifting the aromatic CH stretching band to a lower frequency. The DFT calculations have also revealed in-phase and out-of-phase couplings of the two aromatic CH stretchings in the Raman spectra of 1, which is without intramolecular hydrogen bond due to (+)gauche conformation of 5'-CH2OH moiety. Both coupled vibrational modes are observed in the corresponding experimental spectrum as a single peak because of their similar frequencies. On contrary, aromatic CH stretching modes are not coupled in 2 due to the intramolecular hydrogen bond, resulting in resolution of the Raman bands. Thermal events in DSC and TG curves of 1 and 2 are also in agreement with crystal stoichiometry as observed from single-crystal X-ray diffraction analysis.

Determination of Zalcitabine in Medicaments by Differential Pulse Voltammetry.[Pubmed:26555981]

J Pharm (Cairo). 2013;2013:495814.

The Zalcitabine (ddC) has been extensively used in the treatment of HIV patients due to its antiretroviral activity. The quality control of this active principle in medications is of outstanding importance to public health. The principal objective of the current study was the development of an alternative analytical methodology for the Zalcitabine determination using a voltammetric process. The Zalcitabine gives a reduction peak (at -1.22 V versus Ag/AgCl) at the hanging mercury drop electrode (HMDE). The differential pulse voltammetric response is evaluated with respect to the scan rate (20 mV/s), pulse amplitude (50 mV), support electrolyte (Clark-Lubs buffer), pH (2.0), and other variables. The response is linear over the 10.0 to 28.0 mg/L (47 to 133 muM) concentration range, and the detection limit is 2.08 mg/L. The validation of this method was realized using a governmental Brazilian document (Inmetro, 2007) and the results are reported for medication drugs.

Conjugates of phosphorylated zalcitabine and lamivudine with SiO2 nanoparticles: Synthesis by CuAAC click chemistry and preliminary assessment of anti-HIV and antiproliferative activity.[Pubmed:28169081]

Bioorg Med Chem. 2017 Mar 1;25(5):1696-1702.

Conjugates of phosphorylated dideoxynucleoside antiviral drugs dideoxycytidine (Zalcitabine) and lamivudine with SiO2 nanoparticles were obtained via the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click chemistry between a nucleoside triphosphate containing an alkynyl group at the gamma-phosphate or azidothymidine triphosphate and SiO2 nanoparticles containing alkyl azide or alkynyl groups, respectively. 4-(Prop-2-yn-1-yloxy)butylamino group has been attached to the gamma-phosphate group of dideoxycytidine (Zalcitabine) and lamivudine 5'-triphosphates via the phosphoramidate linkage. New compounds were shown to be potent killers of human colon carcinoma cells. Anti-HIV activity of the conjugates was demonstrated as well. The conjugates of phosphorylated lamivudine and dideoxycytidine (Zalcitabine) showed higher potency than the parent nucleosides. The conjugate of phosphorylated azidothymidine was less active against HIV-1 than the parent nucleoside probably because of the replacement of its 3'-azido group by 1,2,3-triazole ring. These results show an opportunity for using SiO2 nanoparticles as a transport for delivering phosphorylated nucleosides to cells in order to increase their efficiency as antiviral and anticancer drugs.

Description

Zalcitabine is a potent nucleoside analogue reverse transcriptase inhibitor used in the treatment of HIV infection.

Keywords:

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