Page last updated: 2024-12-11

1-arabinofuranosylcytosine-5'-stearylphosphate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

1-arabinofuranosylcytosine-5'-stearylphosphate (Ara-C-Stearyl Phosphate) is a synthetic analog of the antiviral drug cytarabine (Ara-C), also known as cytosine arabinoside.

**Here's what makes Ara-C-Stearyl Phosphate unique and important for research:**

* **Enhanced Delivery:** The addition of the stearyl phosphate group to Ara-C significantly improves its ability to penetrate cell membranes. This enhanced delivery mechanism makes Ara-C-Stearyl Phosphate a promising candidate for:
* **Targeted Drug Delivery:** It can be specifically delivered to target cells or tissues by incorporating the stearyl phosphate moiety into liposomes or other carrier systems.
* **Overcoming Drug Resistance:** Some cancer cells develop resistance to traditional chemotherapy drugs, including Ara-C. Ara-C-Stearyl Phosphate's enhanced delivery could circumvent these resistance mechanisms.

* **Potent Antitumor Activity:** Ara-C-Stearyl Phosphate retains the anticancer activity of Ara-C, acting as an inhibitor of DNA synthesis. This makes it a valuable tool for studying:
* **Cancer Biology:** Understanding the mechanisms of action and resistance of anticancer drugs.
* **New Treatment Strategies:** Developing novel therapies for various types of cancer.

* **Improved Pharmacokinetic Properties:** The stearyl phosphate group alters the pharmacokinetic profile of Ara-C, potentially leading to:
* **Longer Duration of Action:** Increased time the drug remains effective in the body.
* **Reduced Dosage Frequency:** Fewer administrations needed for therapeutic effect.

**Current Research Applications:**

* **Preclinical Studies:** Ara-C-Stearyl Phosphate is actively being studied in preclinical models (in vitro and in vivo) to evaluate its efficacy against various cancer types.
* **Drug Delivery Systems:** Researchers are investigating ways to incorporate Ara-C-Stearyl Phosphate into liposomes, nanoparticles, and other delivery systems to achieve targeted drug delivery.
* **Combination Therapies:** Exploring the potential of Ara-C-Stearyl Phosphate in combination with other anticancer agents to enhance therapeutic outcomes.

**Overall, Ara-C-Stearyl Phosphate is a promising drug candidate with the potential to overcome limitations of traditional Ara-C therapy. It offers researchers a valuable tool for exploring novel cancer treatment strategies and advancing the fight against this disease.**

1-arabinofuranosylcytosine-5'-stearylphosphate: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13491648
SCHEMBL ID13524289
MeSH IDM0169659

Synonyms (5)

Synonym
1-arabinofuranosylcytosine-5'-stearylphosphate
SCHEMBL13524289
SY313379
[(2r,3s,4s,5r)-5-[4-amino-2-oxopyrimidin-1(2h)-yl]-3,4-dihydroxy-2-tetrahydrofuryl]methyl octadecyl hydrogen phosphate
mfcd31746875

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" During a phase I study in patients with advanced low-grade non-Hodgkin lymphomas or acute myeloid leukemia, the pharmacokinetic parameters of Ara-CMP-Stearate (kindly provided by ASTA Medica, Frankfurt, Germany) were determined by HPLC analysis."( Pharmacokinetics of Ara-CMP-Stearate (YNK01): phase I study of the oral Ara-C derivative.
Braess, J; Hiddemann, W; Kaufmann, C; Ramsauer, B; Schleyer, E; Schüssler, M; Unterhalt, M; Wilde, S, 1995
)
0.29
" From all of pharmacokinetic data, the oral administration of SPAC at 150 to 300 mg/m2/day was pharmacokinetically concluded to be comparable to the continuous infusion of ara-C at 20 mg/m2/day."( [A pharmacokinetic study of the value of oral cytarabine ocfosfate in the treatment of hematological malignancies].
Ito, T; Konishi, H; Maesako, Y; Mori, S; Ueda, Y; Yagiri, Y, 1998
)
0.3
" Pharmacokinetic evaluations were performed during 34 treatment cycles in 28 patients."( Oral cytarabine ocfosfate in acute myeloid leukemia and non-Hodgkin's lymphoma--phase I/II studies and pharmacokinetics.
Braess, J; Freund, M; Hanauske, A; Heil, G; Hiddemann, W; Kaufmann, C; Kern, W; Schleyer, E; Schüssler, M, 1998
)
0.3
"Provide pharmacokinetic data for orally administered CO and determine accumulation and functional consequences of Ara-CTP within peripheral blood leukocytes."( Oral cytarabine ocfosfate pharmacokinetics and assessment of leukocyte biomarkers in normal dogs.
Dickinson, PJ; Knych, HK; Kol, A; Pypendop, BH; Questa, M; Rodrigues, CA; Vernau, KM; Vernau, W; Zwueste, DM,
)
0.13

Bioavailability

ExcerptReferenceRelevance
"8% was absorbed and metabolized to AraC and AraU, defining the metabolic bioavailability of this prodrug."( Oral cytarabine ocfosfate in acute myeloid leukemia and non-Hodgkin's lymphoma--phase I/II studies and pharmacokinetics.
Braess, J; Freund, M; Hanauske, A; Heil, G; Hiddemann, W; Kaufmann, C; Kern, W; Schleyer, E; Schüssler, M, 1998
)
0.3

Dosage Studied

ExcerptRelevanceReference
" The dosage for the single and 5-day oral administration ranged 50 to 1,200 and 100 to 900 mg/body/day, respectively."( [Phase I study of YNK01 (1-beta-D-arabinofuranosylcytosine-5'-stearylphosphate)].
Fukuoka, M; Hattori, M; Hirota, Y; Miyazaki, T; Nakamura, T; Niitani, H; Ohta, K; Suzuoki, Y; Tanaka, M; Yoshida, Y, 1990
)
0.28
" The patient has been free of these symptoms on a dosage of 1500 mg cytarabine ocfosfate/day (cycle of 14 days with intervals of 14-21 days) for 24 months and remains in an ongoing partial remission."( Response to cytarabine ocfosfate (YNK01) in a patient with chronic lymphocytic leukemia refractory to treatment with chlorambucil/prednisone, fludarabine, and prednimustine/mitoxantrone.
Braess, J; Hiddemann, W; Kaeser-Fröhlich, A; Kaufmann, CC; Kern, W; Ramsauer, B; Schleyer, E; Schüssler, M; Unterhalt, M, 1996
)
0.29
" After administration of YNK01 at a dosage of 100-150 mg/m2 plasma levels of AraC were comparable to those achieved after low-dose AraC treatment (20 mg/m2) while at doses of YNK01 of 450-600 mg/m2 concentrations of standard-dose AraC (100 mg/m2) were obtained."( Oral cytarabine ocfosfate in acute myeloid leukemia and non-Hodgkin's lymphoma--phase I/II studies and pharmacokinetics.
Braess, J; Freund, M; Hanauske, A; Heil, G; Hiddemann, W; Kaufmann, C; Kern, W; Schleyer, E; Schüssler, M, 1998
)
0.3
" Alternate dosing strategies may enhance the tolerability of YNK01."( Interferon-alpha-2b and oral cytarabine ocfosfate for newly diagnosed chronic myeloid leukaemia.
Arthur, C; Blacklock, H; Bradstock, K; Browett, P; Coulston, J; Gibson, J; Grigg, A; Hawkins, T; Herrmann, R; Hughes, T; Januszewicz, H; Low, C; Martin, N; Mollee, P; Morton, J; Rodwell, R; Schwarer, AP; Seldon, M; Seymour, JF; Shina, S; Spencer, A; Taylor, D; Taylor, KM; Watson, A; Wolf, M; Wright, S, 2004
)
0.32
" Optimal dosing protocols for immunomodulation in dogs have not been defined."( Oral cytarabine ocfosfate pharmacokinetics and assessment of leukocyte biomarkers in normal dogs.
Dickinson, PJ; Knych, HK; Kol, A; Pypendop, BH; Questa, M; Rodrigues, CA; Vernau, KM; Vernau, W; Zwueste, DM,
)
0.13
" Application of functional and active metabolite assessment is feasible and may provide more relevant data to determine optimal dosing regimens for Ara-C-based treatments."( Oral cytarabine ocfosfate pharmacokinetics and assessment of leukocyte biomarkers in normal dogs.
Dickinson, PJ; Knych, HK; Kol, A; Pypendop, BH; Questa, M; Rodrigues, CA; Vernau, KM; Vernau, W; Zwueste, DM,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (55)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (3.64)18.7374
1990's41 (74.55)18.2507
2000's10 (18.18)29.6817
2010's2 (3.64)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials17 (29.82%)5.53%
Reviews2 (3.51%)6.00%
Case Studies21 (36.84%)4.05%
Observational0 (0.00%)0.25%
Other17 (29.82%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]