147-94-4 , Arabinocytidine, CAS: 147-94-4

147-94-4 , Arabinocytidine,
CAS: 147-94-4
C9H13N3O5 / 243.22
MFCD00066487

Arabinocytidine, 阿糖胞苷

1-(b-D-Arabinofuranosyl)cytosine

Cytarabine is also know as cytosine arabinoside (ara-C) and is a chemotherapy drug that works by inhibiting DNA synthesis. It acts as a nucleoside analogue, which is incorporated into the growing DNA chain during replication. Cytarabine combines a cytosine base with an arabinose sugar (1β-arabinofuranosylcytosine) and is an analog for human deoxycytosine. Cytarabine interferes with DNA synthesis as it is rapidly converted to cytosine arabinoside triphosphate, damaging DNA when cells are in the syntheis phase (S phase). Tumor cells which are highly mitotic and growing rapidly are therefore prefertially targeted. Cytarabine also inhibits nucleotide reductase enzymes as well as nuclear polymerases, leading to interruption and inhibition of synthesis, strand breaks and cell death.

Title: Cytarabine

CAS Registry Number: 147-94-4

CAS Name: 4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone

Additional Names: 1-b-D-arabinofuranosylcytosine; Ara-C; b-cytosine arabinoside; aracytidine

Manufacturers' Codes: CHX-3311; U-19920

Trademarks: Alexan (Ebewe); Aracytine (Pfizer); Cytosar (Pharmacia & Upjohn); Depocyte (Pharmacia); Udicil (Pharmacia & Upjohn)

Molecular Formula: C9H13N3O5

Molecular Weight: 243.22

Percent Composition: C 44.44%, H 5.39%, N 17.28%, O 32.89%

Literature References: Nucleoside analog; converted by cellular kinases into the active metabolite, AraCTP. Prepn: J. H. Hunter, US 3116282 (1963 to Upjohn); T. Y. Shen et al., J. Org. Chem. 30, 835 (1965). NMR soln structure of Ara-C within a DNA dodecamer: B. I. Schweitzer et al., Biochemistry 33, 11460 (1994). Crystal structure of complex with human topoisomerase I: J. E. Chrencik et al., J. Biol. Chem. 278, 12461 (2003). Clinical pharmacology and toxicology: R. C. Donehower et al., Cancer Treat. Rep. 70, 1059 (1986). Symposium on clinical pharmacology, pharmacokinetics and efficacy in leukemia: Scand. J. Haematol. 36, Suppl. 44, 1-74 (1986). Review of development of a high dose treatment for acute myeloid leukemia: R. L. Capizzi, Invest. New Drugs 14, 249-256 (1996); of cellular metabolism and mechanism of action: S. Grant, Adv. Cancer Res. 72, 197-233 (1998).

Properties: Crystals from ethanol, mp 212-213°. [a]D24 +153° (c = 0.5 in water). uv max at pH 2: 281.0, 212.5 nm (e 13171, 10230); at pH 12: 272.5 nm (e 9259).

Melting point: mp 212-213°

Optical Rotation: [a]D24 +153° (c = 0.5 in water)

Absorption maximum: uv max at pH 2: 281.0, 212.5 nm (e 13171, 10230); at pH 12: 272.5 nm (e 9259)

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.

CAS Number	147-94-4
Product Name	Cytarabine
IUPAC Name	4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Molecular Formula	C9H13N3O5
Molecular Weight	243.22 g/mol
InChI	InChI=1S/C9H13N3O5/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)/t4-,6-,7+,8-/m1/s1
InChI Key	UHDGCWIWMRVCDJ-CCXZUQQUSA-N
SMILES	C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
Solubility	Freely soluble 1 G IN ABOUT 5 ML WATER & 500 ML ALC; 1 G IN ABOUT 1000 ML CHLOROFORM & 300 ML METHANOL Soluble in water In water, 1X10+6 mg/L at 25 °C (miscible) (est) 4.38e+01 g/L >36.5 [ug/mL]
Synonyms	Ara C, Ara-C, Arabinofuranosylcytosine, Arabinoside, Cytosine, Arabinosylcytosine, Aracytidine, Aracytine, beta Ara C, beta-Ara C, Cytarabine, Cytarabine Hydrochloride, Cytonal, Cytosar, Cytosar U, Cytosar-U, Cytosine Arabinoside
Canonical SMILES	C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
Isomeric SMILES	C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O

CAS No: 147-94-4 Synonyms: Cytosine-b-D-arabinofuranosideCytarabine4-Amino-1-(b-D-Arabinofuranosyl)-2(1H)pyrimidinone MDL No: MFCD00066487 Chemical Formula: C9H13N3O5 Molecular Weight: 243.22

COA:

Name: Cytosine β-D-Arabinofuranoside；Arabinocytidine

CAS: 147-94-4 M.F.: C₉H₁₃N₃O₅ M.W._:243.22

*Items*	*Standards*	*Results*
Appearance	White powder	Positive
Solubility	Soluble in water and almost insoluble in ether	Complies
Appearance of solution	Dissolve1gin 100mL of water, and the solution should be clear and colorless	Complies
Identification	IR and HPLC	Comply
NMR and MS	Should comply	Positive
Residue on ignition	Max. 0.5%	0.02%
Specific rotation	+154°～ +160°	+156°
Heavy metals	Max. 20ppm	Complies
Loss Weight On Dryness	Max. 1%	0.24%
Assay	Min. 99%	99.6%