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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-ArabinofuranosideArabinocytidine       

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%

References:

1. Donehower RC, et al., Cancer Treat. Rep. 1986, 70, p1059

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