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O5508

Sigma-Aldrich

N4-Octadecylcytosine β-D-arabinofuranoside

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H49N3O5
CAS Number:
158233-67-1
Molecular Weight:
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 Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
065H0992

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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.
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
Reto Schwendener et al.
Methods in enzymology, 391, 58-70 (2005-02-22)
Highly lipophilic drugs can be used therapeutically only by the addition of possibly toxic solubilizing agents or by development of complex pharmaceutical formulations. One way of overcoming these disadvantages is the incorporation of such drugs into the bilayer matrix of
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