CAS Number69-74-9
Synonyms2(1H)-pyrimidinone, 1-β-D-arabinofuranosyl-3,4-dihydro-4-imino-, hydrochloride (1:1); Cytosine, 1-β-D-arabino-furanosyl-, hydrochloride; 1-b-D-Arabinofuranosylcytosine Monohydrochloride; Cytosine arabinoside hydrochloride; 1-(β-D-Arabinofuranosyl)-4-imino-3,4-dihydropyrimidin-2(1H)-one hydrochloride (1:1); 1-β-D-Arabinofuranosylcytosine hydrochloride; Ara-cytidine hydrochloride; 4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone Monohydrochloride; u 19920a; 4-Amino-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one hydrochloride (1:1); MFCD00012839; EINECS 200-713-9; 4-Amino-1-(β-D-arabinofuranosyl)-2(1H)-pyrimidinone hydrochloride (1:1); 2(1H)-Pyrimidinone, 4-amino-1-β-D-arabinofuranosyl-, hydrochloride (1:1); 4-amino-1-β-D-arabinofuranosylpyrimidin-2(1H)-one hydrochloride
Molecular FormulaC9H14ClN3O5
Molecular Weight279.68
Purity≥99 (HPLC)%
Boiling Point545.7ºC at 760 mmHg
Melting Point197-198 °C (lit.)
Appearancecrystalline
EINECS200-713-9
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 69-74-9 |
| Catalog No. | 2A-9016988 |
| Chinese Name | 盐酸阿糖胞苷 |
| Synonyms | 2(1H)-pyrimidinone, 1-β-D-arabinofuranosyl-3,4-dihydro-4-imino-, hydrochloride (1:1); Cytosine, 1-β-D-arabino-furanosyl-, hydrochloride; 1-b-D-Arabinofuranosylcytosine Monohydrochloride; Cytosine arabinoside hydrochloride; 1-(β-D-Arabinofuranosyl)-4-imino-3,4-dihydropyrimidin-2(1H)-one hydrochloride (1:1); 1-β-D-Arabinofuranosylcytosine hydrochloride; Ara-cytidine hydrochloride; 4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone Monohydrochloride; u 19920a; 4-Amino-1-(β-D-arabinofuranosyl)pyrimidin-2(1H)-one hydrochloride (1:1); MFCD00012839; EINECS 200-713-9; 4-Amino-1-(β-D-arabinofuranosyl)-2(1H)-pyrimidinone hydrochloride (1:1); 2(1H)-Pyrimidinone, 4-amino-1-β-D-arabinofuranosyl-, hydrochloride (1:1); 4-amino-1-β-D-arabinofuranosylpyrimidin-2(1H)-one hydrochloride |
| Molecular Formula | C9H14ClN3O5 |
| Molecular Weight | 279.68 |
| Purity | ≥99 (HPLC) |
| Boiling Point | 545.7ºC at 760 mmHg |
| Melting Point | 197-198 °C (lit.) |
| Appearance | crystalline |
| Storage Condition | Warehouse Ventilation Low Temperature Drying |
| Application | Cytarabine (AraC) hydrochloride has anti-metabolic and anti-DNA synthesis activity. |
| EINECS | 200-713-9 |
| HTC | 2942000000 |
| PubChem ID | 24278329 |
| MDL Number | MFCD00012839 |
| SMILES | Cl[H].NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O |
| 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 |
| InChI Key | KCURWTAZOZXKSJ-JBMRGDGGSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352208 |
| Hazard Symbols | Transport |
| MSDS | msds/16988_1_69_74_9.pdf |
| Bioactivity | Cytarabine hydrochloride is an antimetabolic agent and DNA synthesis inhibitor with IC50 of 16 nM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer Target IC50: 16 nM (DNA synthesis) 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]. Kinase Assay Stock solution of Cytarabine is prepared in absolute ethanol, and serial dilutions of Cytarabine are prepared. CCRF-CEM cells are suspended in RPMI medium supplemented with 10% FBS, 0.1% gentamicin, and 1% sodium pyruvate. The cells are suspended in their respective media to give 10 mL volumes of cell suspension at a final density of 3-6×104 cells/mL. Appropriate volumes of Cytarabine solution are transferred to the cell suspensions, and incubation is continued for 72 hours. The cells are spun down and resuspended in fresh Cytarabine -free medium, and final cell counts are determined. The data are analyzed by sigmoidal curve fitting of the cell count versus Cytarabine concentration, and the results are expressed as the IC50 (Cytarabine concentration that inhibits cell growth to 50% of the control value). Animal Admin Pregnant rats are injected intraperitoneally (i.p.) with 250 mg/kg of Cytarabine on Day 13 of gestation (GD13). Under the conditions of this experiment, congenital anomalies and growth retardation are detected at a high rate in perinatal fetuses, although the incidence of fetal death is not markedly increased. At 1, 3, 6, 9, 12, 24, and 48 h after the treatment, six dams each are killed by heart puncture under ether anesthesia, and the placentas are collected. As controls, six pregnant rats are injected i.p. with an equivalent volume of PBS on GD13 and killed at the same time point as Cytarabine-treated groups. Of the six dams obtained at each time point, three are used for histopathological analyses and three for reverse transcription-polymerase chain reaction (RT-PCR) analysis. References [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]. 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. [3]. 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. [4]. 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. Chemical & Physical Properties Boiling Point 545.7ºC at 760 mmHg Melting Point 197-198 °C(lit.) Molecular Formula C9H14ClN3O5 Molecular Weight 279.678 Flash Point 283.8ºC Exact Mass 279.062195 PSA 130.83000 InChIKey KCURWTAZOZXKSJ-JBMRGDGGSA-N SMILES Cl.Nc1ccn(C2OC(CO)C(O)C2O)c(=O)n1 Stability Stable. Combustible. Incompatible with strong oxidizing agents. |
| Use of | Cytarabine hydrochloride is an antimetabolic agent and DNA synthesis inhibitor with IC50 of 16 nM. Properties Articles129 Name Cytarabine hydrochloride Synonym More Synonyms Cytarabine hydrochloride Biological Activity Description Cytarabine hydrochloride is an antimetabolic agent and DNA synthesis inhibitor with IC50 of 16 nM. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer IC50: 16 nM (DNA synthesis) 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]. References [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]. 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. [3]. 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. [4]. 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. Chemical & Physical Properties Exact Mass 279.062195 PSA 130.83000 InChIKey KCURWTAZOZXKSJ-JBMRGDGGSA-N Stability Stable. Combustible. Incompatible with strong oxidizing agents. |
| Transport Info | Product name: Purity: 99.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available |
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