cytarabine
4-amino-1-(b-D-arabinofuranosyl)-2(1H)-pyrimidinone
Identification
| Name | cytarabine |
| IUPAC | 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one |
| CAS Number | 147-94-4 |
| EINECS | 205-705-9 |
| FDA UNII | 04079A1RDZ |
| Molecular Formula | C9 H13 N3 O5 |
| Molecular Weight | 243.21961000 |
| MDL Number | MFCD00066487 |
| Nikkaji Number | J2.958K |
| Beilstein | 089175 |
| XlogP3 | -2.10 (est) |
Regulatory
Physical Properties
| Appearance | colorless crystals (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 212.50 °C. @ 760.00 mm Hg |
| Boiling Point | 545.68 °C. @ 760.00 mm Hg (est) |
| Flash Point | 543.00 °F. TCC ( 283.80 °C. ) (est) |
| logP (o/w) | -1.808 (est) |
| Soluble in | water, 1.757e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intravenous-child TDLo 33200 ug/kg/24 |
| Dermal Toxicity | subcutaneous-man TDLo 60 mg/kg/90W-I |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for cytarabine usage levels up to | not for fragrance use. |
| Recommendation for cytarabine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4-
amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
4-
amino-1-(b-D-arabinofuranosyl)-2(1H)-pyrimidinone
4-
amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
4-
amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
4-
amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-2(1H)-pyrimidinone
4-
amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]pyrimidin-2(1H)-one
4-
amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone
arabinocytosine
1-b-D-
arabinofuranosyl-4-amino-2(1H)pyrimidinone
1-(b-D-
arabinofuranosyl)cytosine
1-
arabinofuranosylcytosine
1-b-D-
arabinofuranosylcytosine
arabinoside C
arabinosylcytosine
1-b-D-
arabinosylcytosine
arafcyt
cytarabin
cytarabinoside
cytarabinum
cytarbel
b-
cytosine arabinoside
cytosine b-D-arabinofuranoside
cytosine b-D-arabinoside
cytosine-1-b-arabinofuranoside
cytosine-1-b-D-arabinofuranoside
depocyte
erpalfa
spongocytidine
tarabine
PubMed:
Epigenetic action of decitabine (5-aza-2'-deoxycytidine) is more effective against acute myeloid leukemia than cytotoxic action of cytarabine (ARA-C).
PubMed:
Gemtuzumab ozogamicin: time to resurrect?
PubMed:
Successful importation of cytarabine into the United States during a critical national drug shortage.
PubMed:
Drug shortages delay cancer clinical trials.
PubMed:
Clofarabine in pediatric acute leukemia: current findings and issues.
PubMed:
Chemotherapy drug shortages in the United States: genesis and potential solutions.
PubMed:
Anticancer drug discovery from the marine environment.
PubMed:
Cytarabine induced cerebellar neuronal damage in juvenile rat: correlating neurobehavioral performance with cellular and genetic alterations.
PubMed:
Efforts underway to curb drug shortages.
PubMed:
Use of tyrosine kinase inhibitors for chronic myeloid leukemia: management of patients and practical applications for pharmacy practitioners.
PubMed:
Mechanisms of synergistic antileukemic interactions between valproic acid and cytarabine in pediatric acute myeloid leukemia.
PubMed:
Basic mechanisms of arsenic trioxide (ATO)-induced apoptosis in human leukemia (HL-60) cells.
PubMed:
The odyssey of marine pharmaceuticals: a current pipeline perspective.
PubMed:
Antineoplastic mechanisms of niclosamide in acute myelogenous leukemia stem cells: inactivation of the NF-kappaB pathway and generation of reactive oxygen species.
PubMed:
De novo neurogenesis in adult hypothalamus as a compensatory mechanism to regulate energy balance.
PubMed:
Arsenic and old lace: novel approaches in elderly patients with acute myeloid leukemia.
PubMed:
Polysaccharopeptide enhances the anticancer activity of doxorubicin and etoposide on human breast cancer cells ZR-75-30.
PubMed:
Genotoxicity (mitotic recombination) of the cancer chemotherapeutic agents cisplatin and cytosine arabinoside in Aspergillus nidulans.
PubMed:
Clinical features and correlates of gemcitabine-associated lung injury: findings from the RADAR project.
PubMed:
[Disseminated cutaneous and visceral fusariosis in an aplastic patient: an unusual digestive entry].
PubMed:
Adenomatous polyposis coli influences micronuclei induction by PhIP and acrylamide in mouse erythrocytes.
PubMed:
Low dose Ara-C for myelodysplastic syndromes: is it still a current therapy?
PubMed:
[Glivec in combination with HA regimen for treatment of 20 patients with Ph chromosome positive acute leukemia].
PubMed:
Approval summary: imatinib mesylate capsules for treatment of adult patients with newly diagnosed philadelphia chromosome-positive chronic myelogenous leukemia in chronic phase.
PubMed:
Imatinib mesylate for chronic myeloid leukemia: what do we really know?
PubMed:
Green urine in a critically ill patient.
PubMed:
Mylotarg: antibody-targeted chemotherapy comes of age.
PubMed:
Development of obesity and neurochemical backing in aurothioglucose-treated mice.
PubMed:
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis.
PubMed:
Cardiotoxicity of chemotherapeutic agents: incidence, treatment and prevention.
PubMed:
Involvement of hydrogen peroxide and hydroxyl radical in chemically induced apoptosis of HL-60 cells.
PubMed:
Infrared microspectroscopic imaging of the cerebellum of normal and cytarabine treated rats.
PubMed:
Clinical status and optimal use of topotecan.
PubMed:
Acute pancreatitis associated with continuous infusion cytarabine therapy: a case report.
PubMed:
Advances in therapy for hairy cell leukemia. A review.
PubMed:
[Hypersalivation as a leading symptom of neoplastic meningiosis in highly malignant non-Hodgkin's lymphoma].
PubMed:
Clustering of adverse drug events: analysis of risk factors for cerebellar toxicity with high-dose cytarabine.
PubMed:
Maternal and developmental toxicity of low doses of cytosine arabinoside in mice.
PubMed:
Idarubicin: a second-generation anthracycline.
PubMed:
Physicians warned of high-dose cytarabine.
PubMed:
Increased aortic DNA synthesis precedes renal hypertension in rats. An obligatory step?
PubMed:
Effects of intranasal irrigation with mitotic inhibitors on olfactory behavior and biochemistry in mice.
PubMed:
Character of the stimulatory response of uridine kinase in rat livers to cycloheximide treatment.
PubMed:
Drugs five years later: cytarabine.
PubMed:
Hyponatraemia syndrome in acute myeloid leukaemia.
PubMed:
Current trends in clinical pharmacology in the USA.
PubMed:
Chronic viral neuropathies: models for study and food for thought.