O5508
N4-Octadecylcytosine β-D-arabinofuranoside
别名:
N(4)-octadecyl-ara-C, N4-Stearyl-Ara C, NOAC
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关于此项目
经验公式（希尔记法）:
C27H49N3O5
化学文摘社编号:
分子量:
495.70
UNSPSC Code:
41106305
PubChem Substance ID:
MDL number:
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
SMILES string
CCCCCCCCCCCCCCCCCCNC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O
InChI key
HQHQCEKUGWOYPS-URBBEOKESA-N
form
solid
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
存储类别
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
法规信息
新产品
此项目有
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)
R A Schwendener et al.
Journal of cancer research and clinical oncology, 122(2), 102-108 (1996-01-01)
The oral cytostatic activity in L1210 mouse leukaemia of the two new N4-alkyl derivatives of 1-beta-D-arabinofuranosylcytosine (AraC), N4-hexadecyl- and N4-octadecyl-1-beta-D-arabinofuranosylcytosine (NH-AraC, NO-AraC) was investigated. In contrast to AraC, both derivatives were highly cytostatic after oral application as liposome formulations. With
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
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