Cytarabine hydrochloride

Category	Herpes simplex Virus (HSV)
CAS	69-74-9
Description	Cytarabine, an antimetabolite analogue of cytidine with a modified sugar moiety, is an antimetabolic agent and DNA synthesis inhibitor.

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Product Information

Synonyms	Cytosine arabinoside hydrochloride; 1-beta-D-Arabinofuranosylcytosine hydrochloride; Aracytidine hydrochloride; 4-Amino-1-β-D-arabinofuranosyl-2(1H)-pyrimidinone hydrochloride; Arabinocytidine hydrochloride; Arabinofuranosylcytosine hydrochloride
IUPAC Name	4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
Molecular Weight	279.68
Molecular Formula	C9H14ClN3O5
Canonical SMILES	C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O.Cl
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
InChIKey	KCURWTAZOZXKSJ-JBMRGDGGSA-N
Boiling Point	545.7°C at 760 mmHg
Melting Point	197-198 °C
Flash Point	283.8°C
Purity	95%
Solubility	Soluble in DMSO
Appearance	White powder
Shelf Life	As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage	Store at -20 °C
Complexity	383
Exact Mass	279.0621982
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. 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.
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. 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.
PSA	130.83000
Target	DNA/RNA Synthesis; Nucleoside Antimetabolite/Analog; HSV; Autophagy