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Key Documents

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O5508

Sigma-Aldrich

N4-Octadecylcytosine β-D-arabinofuranoside

Sinónimos:

N(4)-octadecyl-ara-C, N4-Stearyl-Ara C, NOAC

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About This Item

Fórmula empírica (notación de Hill):
C27H49N3O5
Número de CAS:
158233-67-1
Peso molecular:
495.70
MDL number:
MFCD00467196
UNSPSC Code:
41106305
PubChem Substance ID:
24898023

form

solid

SMILES string

CCCCCCCCCCCCCCCCCCNC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

InChI

1S/C27H49N3O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-28-23-18-20-30(27(34)29-23)26-25(33)24(32)22(21-31)35-26/h18,20,22,24-26,31-33H,2-17,19,21H2,1H3,(H,28,29,34)/t22-,24-,25+,26-/m1/s1

InChI key

HQHQCEKUGWOYPS-URBBEOKESA-N

Application

N4-Stearyl-Ara C (N(4)-octadecyl-ara-C, NOAC) is a lipophilic derivative of Ara-C used to improve the incorporation of Ara-C, an anti-cancer agent, into lipid bilayers of liposomes and/or target cells.

Other Notes

Lipophilic, cytotoxic derivative of cytosine arabinoside

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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R A Schwendener et al.
Investigational new drugs, 19(3), 203-210 (2001-09-20)
N4-octadecyl-1-beta-D-arabinofuranosylcytosine (NOAC) is a new lipophilic derivative of 1-beta-D-arabinofuranosylcytosine (ara-C) with potent antitumor activity against leukemias and solid tumors. In this study the activity of NOAC against freshly explanted clonogenic cells from human tumors was determined and compared with conventional
S K Koller-Lucae et al.
British journal of cancer, 80(10), 1542-1549 (1999-07-17)
Low density lipoprotein (LDL) receptor-mediated uptake and cytotoxic effects of N4-octadecyl-1-beta-D-arabinofuranosylcytosine (NOAC) were studied in Daudi lymphoma cells. NOAC was either incorporated into LDL or liposomes to compare specific and unspecific uptake mechanisms. Binding of LDL to Daudi cells was
S K Koller-Lucae et al.
Drug metabolism and disposition: the biological fate of chemicals, 27(3), 342-350 (1999-03-04)
Metabolism and excretion of the new antitumor drug N4-octadecyl-1-beta-D-arabinofuranosylcytosine (NOAC) was investigated in mice. Mice were injected i.v. with tritium-labeled liposomal NOAC (4 micromol/mouse). Analysis of HPLC-purified extracts of liver homogenates by liquid chromatography coupled with mass spectrometry revealed only
K M Rentsch et al.
Journal of chromatography. B, Biomedical applications, 673(2), 259-266 (1995-11-17)
N4-Hexadecyl- and N4-octadecyl-1-beta-D-arabinofuranosylcytosine (NHAC, NOAC) are two new cytostatic derivatives of cytosine arabinoside (ara-C) with improved cytostatic activity and stability against deamination. A high-performance liquid chromatography (HPLC) method was developed for the specific determination of NHAC and NOAC in plasma
Novel PEG-matrix metalloproteinase-2 cleavable peptide-lipid containing galactosylated liposomes for hepatocellular carcinoma-selective targeting.
Terada T, Iwai M, Kawakami S, et al.
J. Controlled Release, 111, 333-342 (2006)
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