Compounds > 5'-oleoyl cytarabine
Page last updated: 2024-12-11

5'-oleoyl cytarabine

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

Description

elaidic acid-cytarabine: a 5'-elaidic acid (C18:1, unsaturated fatty acid) ester of cytarabine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6438895
CHEMBL ID2105665
CHEBI ID177700
SCHEMBL ID15140172
MeSH IDM0137506

Synonyms (42)

Synonym
5'-oleoyl cytarabine
101235-34-1
CHEBI:177700
[(2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl (e)-octadec-9-enoate
elaidic acid-cytarabine
p-4055
cp-4055
elacyt
elacytarabine
ta7wjg93ar ,
elacytarabine [usan:inn]
cp 4055
2(1h)-pyrimidinone, 4-amino-1-(5-o-((9e)-1-oxo-9-octadecenyl)-beta-d-arabinofuranosyl)-
unii-ta7wjg93ar
elacytarabine (usan/inn)
D09712
188181-42-2
CHEMBL2105665
2(1h)-pyrimidinone, 4-amino-1-(5-o-(1-oxo-9-octadecenyl)-beta-d-arabinofuranosyl)-, (z)-
cp4055
5'-oleyl-ara-c
5'-oleoyl cytosine arabinoside
DB05494
elacytarabine [usan]
5'-o-(trans-9''-octadecenoyl)-1-ss-d-arabinofuranosyl cytosine
2(1h)-pyrimidinone, 4-amino-1-(5-o-((9e)-1-oxo-9-octadecen-1-yl)-.beta.-d-arabinofuranosyl)-
elacytarabine [inn]
4-amino-1-(5-o-((9e)-octadec-9-enoyl)-.beta.-d-arabinofuranosyl)pyrimidin-2(1h)-one
elacytarabine [who-dd]
2(1h)-pyrimidinone, 4-amino-1-(5-o-((9e)-1-oxo-9-octadecenyl)-.beta.-d-arabinofuranosyl)-
SCHEMBL15140172
((2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl (e)-octadec-9-enoate
CS-0003647
HY-14941
EX-A3127
5'-o-(elaidoyl) 1-beta-d-arabinofuranosylcytosine
Q27289866
(e)-((2r,3s,4s,5r)-5-(4-amino-2-oxopyrimidin-1(2h)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl octadec-9-enoate.
5/'-oleoyl cytarabine
DTXSID601031218
cytarabine-5'-elaidate
AKOS040741571

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Elacytarabine is clinically active in relapsed/refractory AML: overall response rate (CR + CRi) was 44% (16/36 with 7 non-evaluable patients) and adverse events were manageable."( Elacytarabine in relapsed/refractory acute myeloid leukaemia: an evaluation of clinical efficacy, pharmacokinetics, cardiac safety and effects on lipid profile.
Bergua, JM; Chevassut, T; Duarte, R; Gianella-Borradori, A; Hals, PA; Jacobsen, TF; Johansen, M; Knapper, S; Rasch, W; Salamero, O; Smith, M, 2014)		0.4

Compound-Compound Interactions

ExcerptReferenceRelevance
"The objective of the present study was to determine the in vivo antitumor activity of elacytarabine, the 5'-elaidic acid ester of arabinofuranosyl cytidine, alone and in combination with bevacizumab, cetuximab and trastuzumab in Vascular endothelial growth factor (VEGF), Epidermal growth factor receptor (EGFR)- and Human epidermal growth factor receptor 2 (HER2)-expressing non-small cell lung cancer xenografts."( Antitumor activity of elacytarabine combined with bevacizumab, cetuximab and trastuzumab in human NSCLC xenografts.
Bruheim, S; Fodstad, O; Mælandsmo, GM; Sandvold, ML, 2013)		0.39
"The antitumor activity of elacytarabine, was tested at the maximal tolerable dose (MTD; 50 mg/kg) and half MTD (25 mg/kg), alone and in combination with the antibodies bevacizumab (5 mg/kg), cetuximab (20 mg/kg) and trastuzumab (4 mg/kg) in two human non-small cell lung cancer xenografts."( Antitumor activity of elacytarabine combined with bevacizumab, cetuximab and trastuzumab in human NSCLC xenografts.
Bruheim, S; Fodstad, O; Mælandsmo, GM; Sandvold, ML, 2013)		0.39
" In the elacytarabine-, bevacizumab- and trastuzumab-insensitive MAKSAX xenograft, the combination of either bevacizumab or trastuzumab with elacytarabine at the MTD or half MTD resulted in intermediate activity, suggesting a beneficial effect of the combinations, whereas for cetuximab, the effect was enhanced when combined with elacytarabine given at the MTD, but not half-MTD."( Antitumor activity of elacytarabine combined with bevacizumab, cetuximab and trastuzumab in human NSCLC xenografts.
Bruheim, S; Fodstad, O; Mælandsmo, GM; Sandvold, ML, 2013)		0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pyrimidine nucleoside
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (4.76)18.7374
1990's1 (4.76)18.2507
2000's3 (14.29)29.6817
2010's16 (76.19)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.90 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (33.33%)5.53%
Reviews3 (14.29%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (52.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
cytosine
[no description available]		3.1610aminopyrimidine;
pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
dipyridamole
Dipyridamole: A phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascular endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752). dipyridamole : A pyrimidopyrimidine that is 2,2',2'',2'''-(pyrimido[5,4-d]pyrimidine-2,6-diyldinitrilo)tetraethanol substituted by piperidin-1-yl groups at positions 4 and 8 respectively. A vasodilator agent, it inhibits the formation of blood clots.		2.0710piperidines;
pyrimidopyrimidine;
tertiary amino compound;
tetrol		adenosine phosphodiesterase inhibitor;
EC 3.5.4.4 (adenosine deaminase) inhibitor;
platelet aggregation inhibitor;
vasodilator agent
valproic acid
Valproic Acid: A fatty acid with anticonvulsant and anti-manic properties that is used in the treatment of EPILEPSY and BIPOLAR DISORDER. The mechanisms of its therapeutic actions are not well understood. It may act by increasing GAMMA-AMINOBUTYRIC ACID levels in the brain or by altering the properties of VOLTAGE-GATED SODIUM CHANNELS.. valproic acid : A branched-chain saturated fatty acid that comprises of a propyl substituent on a pentanoic acid stem.		3.1610branched-chain fatty acid;
branched-chain saturated fatty acid		anticonvulsant;
antimanic drug;
EC 3.5.1.98 (histone deacetylase) inhibitor;
GABA agent;
neuroprotective agent;
psychotropic drug;
teratogenic agent
cytarabine
[no description available]		11.36228beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
pyrimidine
pyrimidine : The parent compound of the pyrimidines; a diazine having the two nitrogens at the 1- and 3-positions.		2.0510diazine;
pyrimidines		Daphnia magna metabolite
hydrazine
diamine : Any polyamine that contains two amino groups.		3.5520azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
azacitidine
Azacitidine: A pyrimidine analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent.. 5-azacytidine : An N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via an N-glycosidic linkage. An antineoplastic agent, it is used in the treatment of myeloid leukaemia.		3.1610N-glycosyl-1,3,5-triazine;
nucleoside analogue		antineoplastic agent
deoxycytidine
[no description available]		3.3160pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
camptothecin
NSC 100880: carboxylate (opened lactone) form of camptothecin; RN refers to (S)-isomer; structure given in first source		2.0410delta-lactone;
pyranoindolizinoquinoline;
quinoline alkaloid;
tertiary alcohol		antineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
genotoxin;
plant metabolite
daunorubicin
Daunorubicin: A very toxic anthracycline aminoglycoside antineoplastic isolated from Streptomyces peucetius and others, used in treatment of LEUKEMIA and other NEOPLASMS.. anthracycline : Anthracyclines are polyketides that have a tetrahydronaphthacenedione ring structure attached by a glycosidic linkage to the amino sugar daunosamine.. daunorubicin : A natural product found in Actinomadura roseola.		3.1610aminoglycoside antibiotic;
anthracycline;
p-quinones;
tetracenequinones		antineoplastic agent;
bacterial metabolite
5'-palmitoyl cytarabine
[no description available]		1.9610
idarubicin
Idarubicin: An orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.		4.732anthracycline antibiotic;
deoxy hexoside;
monosaccharide derivative
topotecan
Topotecan: An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA TOPOISOMERASES, TYPE I.. topotecan : A pyranoindolizinoquinoline used as an antineoplastic agent. It is a derivative of camptothecin and works by binding to the topoisomerase I-DNA complex and preventing religation of these 328 single strand breaks.		2.0410pyranoindolizinoquinolineantineoplastic agent;
EC 5.99.1.2 (DNA topoisomerase) inhibitor
gemcitabine
gemcitabine : A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.		2.9740organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic
irinotecan
[no description available]		2.0410carbamate ester;
delta-lactone;
N-acylpiperidine;
pyranoindolizinoquinoline;
ring assembly;
tertiary alcohol;
tertiary amino compound		antineoplastic agent;
apoptosis inducer;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
prodrug
clofarabine
[no description available]		3.1610adenosines;
organofluorine compound		antimetabolite;
antineoplastic agent
imatinib mesylate
imatinib methanesulfonate : A methanesulfonate (mesylate) salt that is the monomesylate salt of imatinib. Used for treatment of chronic myelogenous leukemia and gastrointestinal stromal tumours.		3.1610methanesulfonate saltanticoronaviral agent;
antineoplastic agent;
apoptosis inducer;
tyrosine kinase inhibitor
docetaxel anhydrous
Docetaxel: A semisynthetic analog of PACLITAXEL used in the treatment of locally advanced or metastatic BREAST NEOPLASMS and NON-SMALL CELL LUNG CANCER.. docetaxel anhydrous : A tetracyclic diterpenoid that is paclitaxel with the N-benzyloxycarbonyl group replaced by N-tert-butoxycarbonyl, and the acetoxy group at position 10 replaced by a hydroxy group.		2.0510secondary alpha-hydroxy ketone;
tetracyclic diterpenoid		antimalarial;
antineoplastic agent;
photosensitizing agent
cyc 682
sapacitabine: structure in first source. sapacitabine : A nucleoside analogue resulting from the formal condensation of the carboxy group of hexadecanoic acid with the amino group of CNDAC. It is the prodrug of CNDAC and is currently in clinical development for the treatment of acute myeloid leukemia (AML).		3.1610nitrile;
nucleoside analogue;
secondary carboxamide		antimetabolite;
antineoplastic agent;
DNA synthesis inhibitor;
prodrug
decitabine
[no description available]		3.16102'-deoxyribonucleoside
troxacitabine
troxacitabine: shows good anti-HIV activity without cytotoxicity		3.1610carbohydrate derivative;
nucleobase-containing molecular entity
laromustine
laromustine: has antineoplastic activity		3.5520
cp 4126
CP 4126: the elaidic acid ester of gemcitabine		2.9740pyrimidine 2'-deoxyribonucleoside
ConditionIndicatedRelationship StrengthStudiesTrials
Adverse Drug Event
[description not available]		02.0810
Acute Myelogenous Leukemia
[description not available]		011.02128
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		113.02128
Drug-Related Side Effects and Adverse Reactions
Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.		02.0810
Carcinoma, Non-Small Cell Lung
[description not available]		03.8521
Cancer of Lung
[description not available]		03.8521
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		03.8521
Lung Neoplasms
Tumors or cancer of the LUNG.		03.8521
Recrudescence
[description not available]		08.1155
Bilirubinemia
[description not available]		07.5244
Elevated Cholesterol
[description not available]		07.5244
Hypercholesterolemia
A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.		07.5244
Malignant Melanoma
[description not available]		03.7821
Benign Neoplasms
[description not available]		03.4311
Cancer of Ovary
[description not available]		04.4122
Melanoma
A malignant neoplasm derived from cells that are capable of forming melanin, which may occur in the skin of any part of the body, in the eye, or, rarely, in the mucous membranes of the genitalia, anus, oral cavity, or other sites. It occurs mostly in adults and may originate de novo or from a pigmented nevus or malignant lentigo. Melanomas frequently metastasize widely, and the regional lymph nodes, liver, lungs, and brain are likely to be involved. The incidence of malignant skin melanomas is rising rapidly in all parts of the world. (Stedman, 25th ed; from Rook et al., Textbook of Dermatology, 4th ed, p2445)		15.7821
Neoplasms
New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.		03.4311
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		16.4122
Germinoblastoma
[description not available]		02.4520
Lymphoma
A general term for various neoplastic diseases of the lymphoid tissue.		02.4520
Metastase
[description not available]		02.0510
Neoplasm Metastasis
The transfer of a neoplasm from one organ or part of the body to another remote from the primary site.		02.0510
Leucocythaemia
[description not available]		02.7530
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		02.7530
Hematologic Malignancies
[description not available]		02.0710
Hematologic Neoplasms
Neoplasms located in the blood and blood-forming tissue (the bone marrow and lymphatic tissue). The commonest forms are the various types of LEUKEMIA, of LYMPHOMA, and of the progressive, life-threatening forms of the MYELODYSPLASTIC SYNDROMES.		02.0710
Leukemia L 1210
[description not available]		02.3820
Carcinoma, Anaplastic
[description not available]		0210
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		0210
Experimental Leukemia
[description not available]		0210
Carcinoma
A malignant neoplasm made up of epithelial cells tending to infiltrate the surrounding tissues and give rise to metastases. It is a histological type of neoplasm and not a synonym for cancer.		0210