Cytarabine hydrochlorideDNA synthsis inhibitor CAS# 69-74-9 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 69-74-9 | SDF | Download SDF |
| PubChem ID | 6252 | Appearance | Powder |
| Formula | C9H14ClN3O5 | M.Wt | 279.68 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Cytosine β-D-arabinofuranoside hydrochloride; Cytosine Arabinoside hydrochloride; Ara-C hydrochloride | ||
| Solubility | >14.2mg/mL in DMSO | ||
| Chemical Name | 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride | ||
| SMILES | [Cl-].NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O.[H+] | ||
| Standard InChIKey | KCURWTAZOZXKSJ-JBMRGDGGSA-N | ||
| Standard InChI | InChI=1S/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./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. |
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| 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. |
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| 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. | ||
| Description | Cytarabine hydrochloride is an antimetabolic agent and DNA synthesis inhibitor with IC50 of 16 nM.In Vitro:Cytarabine is phosphorylated into a triphosphate form (Ara-CTP) involving deoxycytidine kinase (dCK), which competes with dCTP for incorporation into DNA, and then blocks DNA synthesis by inhibiting the function of DNA and RNA polymerases. Cytarabine displays a higher growth inhibitory activity towards wild-type CCRF-CEM cells compared to other acute myelogenous leukemia (AML) cells with IC50 of 16 nM[1]. Cytarabine apparently induces apoptosis of rat sympathetic neurons at 10 μM, of which 100 μM shows the highest toxicity and kills over 80% of the neurons by 84 hours, involving the release of mitochondrial cytochrome-c and the activation of caspase-3, and the toxicity can be attenuated by p53 knockdown and delayed by bax deletion[2].In Vivo:Cytarabine (250 mg/kg) also causes placental growth retardation and increases placental trophoblastic cells apoptosis in the placental labyrinth zone of the pregnant Slc:Wistar rats, which increases from 3 hour after the treatment and peaks at 6 hour before returning to control levels at 48 hour, with remarkably enhanced p53 protein, p53 trancriptional target genes such as p21, cyclinG1 and fas and caspase-3 activity[3]. Cytarabine is highly effective against acute leukaemias, which causes the chCytarabineteristic G1/S blockage and synchronization, and increases the survival time for leukaemic Brown Norway rats in a weak dose-related fashion indicating that the use of higher dosages of Cytarabine does not contribute to its antileukaemic effectiveness in man[4]. References: | |||||
Cytarabine hydrochloride Dilution Calculator
Cytarabine hydrochloride Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.5755 mL | 17.8776 mL | 35.7551 mL | 71.5103 mL | 89.3879 mL |
| 5 mM | 0.7151 mL | 3.5755 mL | 7.151 mL | 14.3021 mL | 17.8776 mL |
| 10 mM | 0.3576 mL | 1.7878 mL | 3.5755 mL | 7.151 mL | 8.9388 mL |
| 50 mM | 0.0715 mL | 0.3576 mL | 0.7151 mL | 1.4302 mL | 1.7878 mL |
| 100 mM | 0.0358 mL | 0.1788 mL | 0.3576 mL | 0.7151 mL | 0.8939 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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Cytarabine hydrochloride is an effective drug in the treatment of cancers of white blood cells [1].
Cytarabine hydrochloride is a dxoxycytidine (dC) analogue. Cytarabine hydrochloride has been found to be phosphorylated into a triphophate form, and thus compete with dCTP for incorporation into DNA. Cytarabine hydrochloride has reported to incorporate into DNA and block DNA synthesis by inhibiting the function of DNA and RNA polymerases. In addition, incorporated has shown a growth inhibition dose-dependent curve using acute myelogenous leukemia (AML) in a growth inhibition assay with IC50 values of 16nM,103μM and 223μM for CCRF-CEM, CEM/AraC8C and CEM/dCK-cell lines, respectively. Moreover, Cytarabine hydrochloride has been exhibited to retrovirally transducer rat leukemic KA cells by WST-1 assay with IC50 values of 0.69μM,1.73μM and 0.037μM for KA, kA/GFP and KA/wt, respectively [1,2].
References:
[1] Tobias SC1, Borch RF.Synthesis and biological evaluation of a cytarabine phosphoramidate prodrug. Mol Pharm. 2004 Mar-Apr; 1(2):112-6.
[2] Veuger MJ1, Heemskerk MH, Honders MW, Willemze R, Barge RM.Functional role of alternatively spliced deoxycytidine kinase in sensitivity to cytarabine of acute myeloid leukemic cells. Blood. 2002 Feb 15; 99(4):1373-80.
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The CAG regimen (low-dose cytarabine, aclarubicin hydrochloride and granulocyte colony-stimulating factor) for the treatment of elderly acute myelomonocytic leukaemia: a case study.[Pubmed:11277347]
J Int Med Res. 2001 Jan-Feb;29(1):41-7.
Elderly patients with acute myelomonocytic leukaemia (AMMoL) frequently have a poor quality of life after induction of remission using high-intensity treatment; we seek a more appropriate regimen for such patients. An 86-year-old man was hospitalized with a diagnosis of AMMoL (FAB classification M4), of abnormal karyotype, and complications of diabetes mellitus and complete right bundle branch block. He was treated with CAG therapy (cytarabine 10 mg/m2 subcutaneously every 12 h for 14 consecutive days; aclarubicin hydrochloride 10 mg/m2 per day, bolus intravenously for 4 consecutive days; granulocyte colony-stimulating factor 100 microg/day, subcutaneous injection for 14 consecutive days) every 3 months. White blood cell counts were at their lowest (around 600 - 800/microl) 12 days after the end of therapy, but returned to about 2000 - 2300/microl 30 days after stopping therapy. No symptoms of drug-related toxicity, except slight nausea, were found. Complete remission with a good quality of life was induced and lasted over 2 years suggesting that CAG therapy might prove effective in elderly patients with AMMoL.
Nonionic surfactant vesicles (niosomes) of cytarabine hydrochloride for effective treatment of leukemias: encapsulation, storage, and in vitro release.[Pubmed:10697760]
Drug Dev Ind Pharm. 2000 Feb;26(2):217-22.
Niosome vesicles of Cytarabine hydrochloride were prepared by a lipid hydration method that excluded dicetylphosphate. The sizes of the vesicles obtained ranged from 600 to 1000 nm, with the objective of producing more blood levels in vivo. The study of the release of drug from niosomes exhibited a prolonged release profile as studied over a period of 16 hr. The drug entrapment efficiency was about 80% with Tween 80, Span 60 and Tween 20; for Span 80, it was 67.5%. The physical stability profile of vesicular suspension was good as studied over a period of 4 weeks.
Stability of fluorouracil, cytarabine, or doxorubicin hydrochloride in ethylene vinylacetate portable infusion-pump reservoirs.[Pubmed:1598939]
Am J Hosp Pharm. 1992 Mar;49(3):619-23.
The stability of fluorouracil, cytarabine, and doxorubicin hydrochloride in admixtures stored in portable infusion-pump reservoirs was investigated. Admixtures containing fluorouracil 50 or 10 mg/mL, cytarabine 25 or 1.25 mg/mL, or doxorubicin hydrochloride 1.25 or 0.5 mg/mL in 0.9% sodium chloride injection or 5% dextrose injection were placed in 80-mL ethylene vinylacetate drug reservoirs protected from light, and 1-mL quantities were withdrawn immediately after preparation and after storage for 1, 2, 3, 4, 7, 14, and 28 days at 4, 22, or 35 degrees C. For each condition, three samples from each admixture were tested for drug concentration by stability-indicating high-performance liquid chromatography. The admixtures were also monitored for precipitation, color change, and pH. Evaporative water loss from the containers was measured. Fluorouracil was stable at all temperatures for 28 days. Cytarabine was stable for 28 days at 4 and 22 degrees C and for 7 days at 35 degrees C. Doxorubicin hydrochloride was stable for 14 days at 4 and 22 degrees C and for 7 days at 35 degrees C. No color change or precipitation was observed, and pH values were stable. Loss of water through the reservoirs was substantial only at 35 degrees C for 28 days. When stored in ethylene vinylacetate portable infusion-pump reservoirs, fluorouracil, cytarabine, and doxorubicin hydrochloride were each stable for at least one week at temperatures up to 35 degrees C. Cytarabine and doxorubicin hydrochloride showed decreasing stability at longer storage times and higher temperatures.
