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Cytarabine hydrochloride

Catalog No. T1272L   CAS 69-74-9
Synonyms: Ara-C hydrochloride, Cytosine Arabinoside hydrochloride

Cytarabine hydrochloride (Ara-C hydrochloride) is a nucleoside analog that causes S phase cell cycle arrest and inhibits DNA polymerase. Cytarabine inhibits DNA synthesis with an IC 50 of 16 nM. Cytarabine hydrochloride has antiviral effects against HSV.

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Cytarabine hydrochloride Chemical Structure
Cytarabine hydrochloride, CAS 69-74-9
Pack Size Availability Price/USD Quantity
50 mg In stock $ 33.00
100 mg In stock $ 47.00
200 mg In stock $ 68.00
500 mg In stock $ 112.00
1 mL * 10 mM (in DMSO) In stock $ 52.00
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Purity: 99.62%
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Biological Description
Chemical Properties
Storage & Solubility Information
Description Cytarabine hydrochloride (Ara-C hydrochloride) is a nucleoside analog that causes S phase cell cycle arrest and inhibits DNA polymerase. Cytarabine inhibits DNA synthesis with an IC 50 of 16 nM. Cytarabine hydrochloride has antiviral effects against HSV.
In vitro Cytarabine is converted into its active form, Ara-CTP (tri-phosphate), by the enzyme deoxycytidine kinase (dCK). It then competes with the natural nucleotide dCTP for incorporation into DNA, ultimately inhibiting DNA synthesis by disrupting DNA and RNA polymerases' functions. This compound exhibits potent growth inhibitory effects on wild-type CCRF-CEM cells, with an IC50 of 16 nM, showcasing higher efficacy compared to other acute myelogenous leukemia (AML) cells. Moreover, Cytarabine is capable of inducing apoptosis in rat sympathetic neurons at a concentration of 10 μM, with the highest observed toxicity at 100 μM, resulting in over 80% cell death within 84 hours. This process involves the release of mitochondrial cytochrome-c and activation of caspase-3, with noted attenuation of toxicity via p53 knockdown and a delay through bax deletion.
In vivo Cytarabine (250 mg/kg) induces placental growth retardation and elevates apoptosis of trophoblastic cells in the placental labyrinth zone in pregnant Slc:Wistar rats. This effect begins 3 hours post-treatment, peaks at 6 hours, and reverts to baseline at 48 hours. It notably increases p53 protein levels and the expression of p53 transcriptional target genes, such as p21, cyclinG1, fas, and activates caspase-3 [3]. Additionally, Cytarabine effectively combats acute leukemias by causing a characteristic G1/S phase block and cell synchronization, thereby extending the survival of leukemic Brown Norway rats. Its effectiveness shows a weak dose-related pattern, suggesting that higher doses do not enhance its anti-leukemic effect in humans [4].
Synonyms Ara-C hydrochloride, Cytosine Arabinoside hydrochloride
Molecular Weight 279.68
Formula C9H14ClN3O5
CAS No. 69-74-9

Storage

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 45 mg/mL (160.9 mM), Sonication is recommended.

TargetMolReferences and Literature

1. Tobias, S.C. and R.F. Borch, Synthesis and biological evaluation of a cytarabine phosphoramidate prodrug. Mol Pharm, 2004. 1(2): p. 112-6. 2. Shepshelovich D, et al. Pharmacodynamics of cytarabine induced leucopenia: a retrospective cohort study. Br J Clin Pharmacol. 2015 Apr;79(4):685-91. 3. Besirli, C.G., et al. Cytosine arabinoside rapidly activates Bax-dependent apoptosis and a delayed Bax-independent death pathway in sympathetic neurons. Cell Death Differ, 2003. 10(9): p. 1045-58. 4. Yamauchi, H., et al., Involvement of p53 in 1-beta-D-arabinofuranosylcytosine-induced trophoblastic cell apoptosis and impaired proliferation in rat placenta. Biol Reprod, 2004. 70(6): p. 1762-7. 5. Richel, D.J., et al., Comparison of the antileukaemic activity of 5 aza-2-deoxycytidine and arabinofuranosyl-cytosine in rats with myelocytic leukaemia. Br J Cancer, 1988. 58(6): p. 730-3. 6. Renis HE. Antiviral activity of cytarabine in herpesvirus-infected rats. Antimicrob Agents Chemother. 1973 Oct;4(4):439-44.

Related compound libraries

This product is contained In the following compound libraries:
Inhibitor Library Drug Repurposing Compound Library Anti-Cancer Clinical Compound Library Anti-Cancer Drug Library Anti-Cancer Approved Drug Library EMA Approved Drug Library Anti-Cancer Active Compound Library DNA Damage & Repair Compound Library Approved Drug Library FDA-Approved & Pharmacopeia Drug Library

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Keywords

Cytarabine hydrochloride 69-74-9 Cell Cycle/Checkpoint DNA Damage/DNA Repair DNA/RNA Synthesis Ara-C hydrochloride Cytarabine Hydrochloride Cytosine Arabinoside Hydrochloride Cytosine Arabinoside hydrochloride Ara-C Hydrochloride inhibitor inhibit

 

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