EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

cytarabine
4-amino-1-(b-D-arabinofuranosyl)-2(1H)-pyrimidinone

Supplier Sponsors

Name:4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CAS Number: 147-94-4Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:205-705-9
FDA UNII: 04079A1RDZ
Nikkaji Web:J2.958K
Beilstein Number:089175
MDL:MFCD00066487
XlogP3:-2.10 (est)
Molecular Weight:243.21961000
Formula:C9 H13 N3 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Cytarabine ≥98%
George Uhe Company
Cytarabine
Glentham Life Sciences
Cytarabine
Sigma-Aldrich: Sigma
For experimental / research use only.
Cytosine β-D-arabinofuranoside crystalline, ≥90% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intravenous-child TDLo 33200 ug/kg/24
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Cancer Vol. 42, Pg. 53, 1978.

intravenous-human TDLo 17241 mg/kg/6D
SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"
Annals of Internal Medicine. Vol. 102, Pg. 556, 1985.

intravenous-man LDLo 1536 mg/kg/43W
PERIPHERAL NERVE AND SENSATION: FASCICULATIONS BEHAVIORAL: ATAXIA
Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 177, 1987.

intravenous-man TDLo 23500 ug/kg/7D
SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE
American Journal of Ophthalmology. Vol. 113, Pg. 587, 1992.

intravenous-man TDLo 649 mg/kg/4D-I
PERIPHERAL NERVE AND SENSATION: FASCICULATIONS
Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 177, 1987.

intraperitoneal-mouse LD50 3779 mg/kg
Cancer Research. Vol. 39, Pg. 2204, 1979.

intravenous-mouse LD50 > 7000 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

oral-mouse LD50 3150 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

intraperitoneal-rat LD50 > 5000 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

intravenous-rat LD50 > 5000 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

oral-rat LD50 > 5000 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

Dermal Toxicity:
subcutaneous-man TDLo 60 mg/kg/90W-I
BLOOD: CHANGES IN SPLEEN SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR BEHAVIORAL: ATAXIA
Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 798, 1987.

subcutaneous-mouse LD50 > 10000 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

subcutaneous-rat LD50 > 5000 mg/kg
Drugs in Japan Vol. 6, Pg. 321, 1982.

Inhalation Toxicity:
Not determined
 
Safety in Use Information:
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.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :6253
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Chemidplus:0000147944
EPA/NOAA CAMEO:hazardous materials
 
References:
 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6253
Pubchem (sid):134975262
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C02961
HMDB (The Human Metabolome Database):HMDB15122
FooDB:FDB001979
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
Formulations/Preparations:
depocyt is available in 5 ml, ready-to-use, single-use vials containing 50 mg of cytarabine. depocyt is formulated as a sterile, nonpyrogenic, white to off-white suspension of cytarabine in sodium chloride 0.9% wv in water for injection. depocyt is preservative-free. cytarabine, the active ingredient, is present at a concentration of 10 mgml and is encapsulated in the particles. inactive ingredients at their respective approximate concentrations are cholesterol, 4.1 mgml; triolein, 1.2 mgml; dioleoylphosphatidylcholine (dopc), 5.7 mgml; and dipalmitoylphosphatidylglycerol (dppg), 1.0 mgml. the ph of the product falls within the range from 5.5 to 8.5. cytarabine liposome injection
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 xerocomus nigromaculatus
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
a pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia. cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of dna. its actions are specific for the s phase of the cell cycle. it also has antiviral and immunosuppressant properties. (from martindale, the extra pharmacopoeia, 30th ed, p472) Isol. from the mushroom Xerocomus nigromaculatus of unknown palatability Cytarabine is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute myelogenous leukemia and meningeal leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. Cytarabine is metabolized intracellularly into its active triphosphate form (cytosine arabinoside triphosphate). This metabolite then damages DNA by multiple mechanisms, including the inhibition of alpha-DNA polymerase, inhibition of DNA repair through an effect on beta-DNA polymerase, and incorporation into DNA. The latter mechanism is probably the most important. Cytotoxicity is highly specific for the S phase of the cell cycle.; Cytarabine, or cytosine arabinoside, is a chemotherapy agent used mainly in the treatment of hematological malignancies such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It is also known as ara C.; Cytosine arabinoside is an antimetabolic agent with the chemical name of 1?-arabinofuranosylcytosine. Its mode of action is due to its rapid conversion into cytosine arabinoside triphosphate, which damages DNA when the cell cycle holds in the S phase (synthesis of DNA). Rapidly dividing cells, which require DNA replication for mitosis, are therefore most affected. Cytosine arabinoside also inhibits both DNA and RNA polymerases and nucleotide reductase enzymes needed for DNA synthesis.
Please share your Comments.
Email Address:
Top of Page Home
Copyright © 1980-2021 The Good Scents Company (tgsc) ™ Disclaimer Privacy Policy