Record Information |
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Version | 1.0 |
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Creation Date | 2014-10-14 21:16:36 UTC |
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Update Date | 2016-10-28 10:04:08 UTC |
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Accession Number | CHEM003932 |
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Identification |
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Common Name | Cytarabine |
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Class | Small Molecule |
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Description | 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) |
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Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
- STOFF IDENT Compounds
- Suspected Compounds - Waste Water
- Suspected Compounds – Schymanski Project
- T3DB toxins
- ToxCast & Tox21 Chemicals
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Contaminant Type | - Antimetabolite, Antineoplastic
- Antiviral Agent
- Drug
- Immunosuppressive Agent
- Metabolite
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Value | Source |
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1-beta-D-Arabinofuranosylcytosine | ChEBI | 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone | ChEBI | Ara-C | ChEBI | Arabinocytosine | ChEBI | Arabinoside C | ChEBI | Citarabina | ChEBI | Cytarabinum | ChEBI | Cytosine arabinoside | ChEBI | Cytosine-1-beta-D-arabinofuranoside | ChEBI | Cytosine-beta-D-arabinofuranoside | ChEBI | Depocyt | Kegg | 1-b-D-Arabinofuranosylcytosine | Generator | 1-Β-D-arabinofuranosylcytosine | Generator | 4-Amino-1-b-D-arabinofuranosyl-2(1H)-pyrimidinone | Generator | 4-Amino-1-β-D-arabinofuranosyl-2(1H)-pyrimidinone | Generator | Cytosine-1-b-D-arabinofuranoside | Generator | Cytosine-1-β-D-arabinofuranoside | Generator | Cytosine-b-D-arabinofuranoside | Generator | Cytosine-β-D-arabinofuranoside | Generator | (beta-D-Arabinofuranosyl)cytosine | HMDB | 1-Arabinofuranosylcytosine | HMDB | 1-beta -D-Arabinofaranosylcytosine | HMDB | 1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone | HMDB | 1-beta -D-Arabinofuranosylcytosine | HMDB | 1-beta-D-Arabinofaranosylcytosine | HMDB | 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone | HMDB | 1-beta-D-Arabinofuranosyl-cytosine | HMDB | 1-beta-D-Arabinofuranosylcytosine, cytosine arabinoside | HMDB | 1-beta-D-Arabinosyl-cytosine | HMDB | 1-beta-D-Arabinosylcytosine | HMDB | 1beta -Arabinofuranasylcytosine | HMDB | 1beta -D-Arabinofuranosylcytosine | HMDB | 1beta -D-Arabinosylcytosine | HMDB | 1beta-Arabinofuranasylcytosine | HMDB | 1beta-D-Arabinofuranosylcytosine | HMDB | 1beta-D-Arabinosylcytosine | HMDB | 2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl | HMDB | 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin | HMDB | 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine | HMDB | 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone | HMDB | 4-Amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one | HMDB | Alexan | HMDB | Arabinocytidine | HMDB | Arabinofuranosylcytosine | HMDB | Arabinosylcytosine | HMDB | Arabitin | HMDB | AraC | HMDB | Aracytidine | HMDB | Aracytin | HMDB | Aracytine | HMDB | Arafcyt | HMDB | beta -Arabinosylcytosine | HMDB | beta -Cytosine arabinoside | HMDB | beta -D-Arabinosylcytosine | HMDB | beta-Ara c | HMDB | beta-Arabinosylcytosine | HMDB | beta-Cytosine arabinoside | HMDB | beta-D-Arabinosylcytosine | HMDB | Cytarabin | HMDB | Cytarabina | HMDB | Cytarabine liposome injection | HMDB | Cytarabinoside | HMDB | Cytonal | HMDB | Cytosar | HMDB | Cytosar-u | HMDB | Cytosine 1-beta-D-arabinofuranoside | HMDB | Cytosine arabinofuranoside | HMDB | Cytosine arabinose | HMDB | Cytosine beta-D-arabinofuranoside | HMDB | Cytosine beta-D-arabinoside | HMDB | Cytosine, beta -D-arabinoside | HMDB | Cytosine, beta-D-arabinoside | HMDB | Cytosine-1-beta-D-arabinofuranoside hydrochloride | HMDB | Cytosine-beta -arabinoside | HMDB | Cytosine-beta -D-arabinofuranoside | HMDB | Cytosine-beta-arabinoside | HMDB | Cytosinearabinoside | HMDB | Depocyte | HMDB | Erpalfa | HMDB | Iretin | HMDB | Spongocytidine | HMDB | Tarabine | HMDB | Udicil | HMDB | Arabinoside, cytosine | HMDB | CytosarU | HMDB | Hydrochloride, cytarabine | HMDB | Cytarabine hydrochloride | HMDB | Cytosar u | HMDB | Ara C | HMDB | beta Ara C | HMDB | Cytarabine | MeSH |
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Chemical Formula | C9H13N3O5 |
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Average Molecular Mass | 243.217 g/mol |
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Monoisotopic Mass | 243.086 g/mol |
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CAS Registry Number | 147-94-4 |
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IUPAC Name | 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one |
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Traditional Name | cytarabine |
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SMILES | NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1 |
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InChI Key | UHDGCWIWMRVCDJ-CCXZUQQUSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Pyrimidine nucleosides |
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Sub Class | Not Available |
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Direct Parent | Pyrimidine nucleosides |
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Alternative Parents | |
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Substituents | - Pyrimidine nucleoside
- Glycosyl compound
- N-glycosyl compound
- Pentose monosaccharide
- Aminopyrimidine
- Pyrimidone
- Hydropyrimidine
- Monosaccharide
- Pyrimidine
- Imidolactam
- Tetrahydrofuran
- Heteroaromatic compound
- Secondary alcohol
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Primary alcohol
- Organic oxide
- Organooxygen compound
- Organonitrogen compound
- Amine
- Alcohol
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | 186-188 | Boiling Point | Not Available | Solubility | Freely soluble |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | splash10-08ml-9320000000-b032ad2c3dbed3face55 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) | splash10-0fuu-3934200000-7c3baaaffddf6aacd0f3 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0zfr-2951000000-7baf0e1ea8b1a34362e2 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0g4j-2980000000-9337623aef7fec22dd97 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS | splash10-0zfr-2951000000-7baf0e1ea8b1a34362e2 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS | splash10-0g4j-2980000000-9337623aef7fec22dd97 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0190000000-eff861edb69ddab2c195 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0900000000-4b5b14f0a5467db173b6 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-3900000000-d85ae6c771dd9206c4c2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-06sl-9600000000-b154ca170372bcbf8a4a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00lu-9200000000-840df44a2d1149f4a7f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-01ox-0790000000-270551529aa609aa9ce8 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-855a7f8775ed4351b290 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-50671582f88f6b4d8cee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-1900000000-54269291900f80d353c3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-7900000000-ae3ff52581cbe6141064 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-03di-0900000000-9f3ae8e87da22e4e2e82 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0910000000-9575881412c4c94a7eae | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-5900000000-2cb5f7e3dbd7baa35b56 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dj-9600000000-7d281b2b2d57c8786e11 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01ox-0960000000-db9207082a1fabf42dae | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xs-4910000000-c89de30dd376cbcb3b66 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-5715839499753b91f845 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available |
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2D NMR | [1H,1H] 2D NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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Toxicity Profile |
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Route of Exposure | Less than 20% of the orally administered dose is absorbed from the gastrointestinal tract. |
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Mechanism of Toxicity | Cytarabine acts through direct DNA damage and incorporation into DNA. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture. It exhibits cell phase specificity, primarily killing cells undergoing DNA synthesis (S-phase) and under certain conditions blocking the progression of cells from the G1 phase to the S-phase. Although the mechanism of action is not completely understood, it appears that cytarabine acts through the inhibition of DNA polymerase. A limited, but significant, incorporation of cytarabine into both DNA and RNA has also been reported. |
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Metabolism | Hepatic. |
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Toxicity Values | Cytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise. |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Status | Value | Unit | Sample Location | Reference |
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Not Detected | | | | |
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External Links |
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DrugBank ID | DB00987 |
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HMDB ID | HMDB0015122 |
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FooDB ID | FDB001216 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Cytarabine |
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Chemspider ID | 6017 |
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ChEBI ID | 28680 |
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PubChem Compound ID | 6253 |
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Kegg Compound ID | C02961 |
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YMDB ID | YMDB00051 |
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ECMDB ID | ECMDB00089 |
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References |
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Synthesis Reference | Michael Kluge, Herbert Schott, “Cytarabine derivatives, the preparation and use thereof.” U.S. Patent US5641758, issued August, 1992. |
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MSDS | Not Available |
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General References | 1. Qu, Guirong; Yang, Xining; Shen, Yanhong; Dong, Chunhong; Guo, Haiming; Wang, Xiuqiang; Wang, Dongchao. Synthesis of cytidine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 11pp. | 2. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386 | 3. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) | 4. Zaky DA, Betts RF, Douglas RG Jr, Bengali K, Neil GL: Varicella-zoster virus and subcutaneous cytarabine: correlation of in vitro sensitivities to blood levels. Antimicrob Agents Chemother. 1975 Mar;7(3):229-32. | 5. Relling MV, Mulhern RK, Fairclough D, Baker D, Pui CH: Chlorpromazine with and without lorazepam as antiemetic therapy in children receiving uniform chemotherapy. J Pediatr. 1993 Nov;123(5):811-6. | 6. Mallick KS, Hajek AS, Parrish RK 2nd: Fluorouracil (5-FU) and cytarabine (ara-C) inhibition of corneal epithelial cell and conjunctival fibroblast proliferation. Arch Ophthalmol. 1985 Sep;103(9):1398-402. | 7. Bursztyn J, Boccara JF, Paillassou B, Bavoux F: [Corneal toxicity of cytarabine. Apropos of a case]. Ophtalmologie. 1989 Jun-Aug;3(3):229-30. | 8. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC. | 9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15492802 |
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