Record Information |
---|
Version | 2.0 |
---|
Creation Date | 2014-10-14 21:16:36 UTC |
---|
Update Date | 2014-12-24 20:27:01 UTC |
---|
Accession Number | T3D4978 |
---|
Identification |
---|
Common Name | Cytarabine |
---|
Class | Small Molecule |
---|
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) |
---|
Compound Type | - Antimetabolite, Antineoplastic
- Antiviral Agent
- Drug
- Immunosuppressive Agent
- Metabolite
- Synthetic Compound
|
---|
Chemical Structure | |
---|
Synonyms | Synonym | (beta-D-arabinofuranosyl)cytosine | 1-Arabinofuranosylcytosine | 1-beta -D-Arabinofaranosylcytosine | 1-beta -D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone | 1-beta -D-Arabinofuranosylcytosine | 1-beta-D-Arabinofaranosylcytosine | 1-beta-D-Arabinofuranosyl-4-amino-2(1H)pyrimidinone | 1-beta-D-Arabinofuranosyl-Cytosine | 1-beta-D-Arabinofuranosylcytosine | 1-beta-D-Arabinofuranosylcytosine, Cytosine Arabinoside | 1-beta-D-Arabinosyl-Cytosine | 1-beta-D-Arabinosylcytosine | 1beta -Arabinofuranasylcytosine | 1beta -D-Arabinofuranosylcytosine | 1beta -D-Arabinosylcytosine | 1beta-Arabinofuranasylcytosine | 1beta-D-Arabinofuranosylcytosine | 1beta-D-Arabinosylcytosine | 2(1H)-Pyrimidinone, 4-amino-1- -D-arabinofuranosyl | 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin | 4-Amino-1-arabinofuranosyl-2-oxo-1,2-dihydropyrimidine | 4-Amino-1-b-D-arabinofuranosyl-2-(1H)-pyrimidinone | 4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinone | 4-amino-1-beta-D-arabinofuranosylpyrimidin-2(1H)-one | Alexan | Ara-C | Arabinocytidine | Arabinofuranosyl Cytidine | Arabinofuranosylcytosine | Arabinosylcytosine | Arabitin | AraC | Aracytidine | Aracytin | Aracytine | Arafcyt | beta -arabinosylcytosine | beta -cytosine arabinoside | beta -D-arabinosylcytosine | beta-Ara c | beta-Arabinosylcytosine | beta-Cytosine arabinoside | beta-D-Arabinosylcytosine | Citarabina | Cytarabin | Cytarabina | Cytarabine liposome injection | Cytarabinoside | Cytarabinum | Cytonal | Cytosar | Cytosar-U | Cytosine 1-beta-D-arabinofuranoside | Cytosine arabinofuranoside | Cytosine arabinose | Cytosine arabinoside | Cytosine beta-D-arabinofuranoside | Cytosine beta-D-arabinoside | Cytosine, beta -D-arabinoside | Cytosine, beta-D-arabinoside | Cytosine-1-beta-D-arabinofuranoside | Cytosine-1-beta-D-arabinofuranoside hydrochloride | Cytosine-beta -arabinoside | Cytosine-beta -D-arabinofuranoside | Cytosine-beta-arabinoside | Cytosine-beta-D-arabinofuranoside | cytosine-β-D-arabinofuranoside | Cytosinearabinoside | Depocyt | Depocyte | Erpalfa | Iretin | Spongocytidine | Tarabine | Udicil |
|
---|
Chemical Formula | C9H13N3O5 |
---|
Average Molecular Mass | 243.217 g/mol |
---|
Monoisotopic Mass | 243.086 g/mol |
---|
CAS Registry Number | 147-94-4 |
---|
IUPAC Name | 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one |
---|
Traditional Name | cytarabine |
---|
SMILES | [H][C@]1(CO)O[C@@]([H])(N2C=CC(=N)N=C2O)[C@@]([H])(O)[C@]1([H])O |
---|
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 |
---|
InChI Key | InChIKey=UHDGCWIWMRVCDJ-CCXZUQQUSA-N |
---|
Chemical Taxonomy |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Nucleosides, nucleotides, and analogues |
---|
Class | Pyrimidine nucleosides |
---|
Sub Class | Not Available |
---|
Direct Parent | Pyrimidine nucleosides |
---|
Alternative Parents | |
---|
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
|
---|
Molecular Framework | Aromatic heteromonocyclic compounds |
---|
External Descriptors | |
---|
Biological Properties |
---|
Status | Detected and Not Quantified |
---|
Origin | Endogenous |
---|
Cellular Locations | |
---|
Biofluid Locations | Not Available |
---|
Tissue Locations | Not Available |
---|
Pathways | Not Available |
---|
Applications | Not Available |
---|
Biological Roles | Not Available |
---|
Chemical Roles | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Appearance | Not Available |
---|
Experimental Properties | Property | Value |
---|
Melting Point | 186-188 | Boiling Point | Not Available | Solubility | Freely soluble | LogP | -2.8 |
|
---|
Predicted Properties | |
---|
Spectra |
---|
Spectra | Spectrum Type | Description | Splash Key | View |
---|
GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0zfr-2951000000-7baf0e1ea8b1a34362e2 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (4 TMS) | splash10-0g4j-2980000000-9337623aef7fec22dd97 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0zfr-2951000000-7baf0e1ea8b1a34362e2 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0g4j-2980000000-9337623aef7fec22dd97 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-08ml-9320000000-b032ad2c3dbed3face55 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0fuu-3934200000-7c3baaaffddf6aacd0f3 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0006-0190000000-eff861edb69ddab2c195 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0900000000-4b5b14f0a5467db173b6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-3900000000-d85ae6c771dd9206c4c2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-06sl-9600000000-b154ca170372bcbf8a4a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00lu-9200000000-840df44a2d1149f4a7f7 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-01ox-0790000000-270551529aa609aa9ce8 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-855a7f8775ed4351b290 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0900000000-50671582f88f6b4d8cee | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-1900000000-54269291900f80d353c3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-7900000000-ae3ff52581cbe6141064 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-03di-0900000000-9f3ae8e87da22e4e2e82 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0btc-3910000000-0c7172b1308a7ac699d4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-03di-0900000000-204e273853aa2d8e09ab | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0910000000-9575881412c4c94a7eae | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-5900000000-2cb5f7e3dbd7baa35b56 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dj-9600000000-7d281b2b2d57c8786e11 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-01ox-0960000000-db9207082a1fabf42dae | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03xs-4910000000-c89de30dd376cbcb3b66 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00kf-9200000000-5715839499753b91f845 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0900000000-61fe3ac4032a2baf1b89 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-2900000000-230b224d4d0dd71d0a49 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02t9-9200000000-7262e80c4fe078b890fc | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2900000000-66dec45988a096cc3483 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ox-9500000000-bc463e76fd8ac42ac1d0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9100000000-98e1626c7f485521a57f | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
|
---|
Toxicity Profile |
---|
Route of Exposure | Less than 20% of the orally administered dose is absorbed from the gastrointestinal tract. |
---|
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. |
---|
Metabolism | Hepatic. |
---|
Toxicity Values | Cytarabine syndrome may develop - it is characterized by fever, myalgia, bone pain, occasionally chest pain, maculopapular rash, conjunctivitis, and malaise. |
---|
Lethal Dose | Not Available |
---|
Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
---|
Uses/Sources | For the treatment of acute non-lymphocytic leukemia, acute lymphocytic leukemia and blast phase of chronic myelocytic leukemia. |
---|
Minimum Risk Level | Not Available |
---|
Health Effects | Not Available |
---|
Symptoms | Not Available |
---|
Treatment | Not Available |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| Not Available |
---|
External Links |
---|
DrugBank ID | DB00987 |
---|
HMDB ID | HMDB15122 |
---|
PubChem Compound ID | 6253 |
---|
ChEMBL ID | CHEMBL803 |
---|
ChemSpider ID | 6017 |
---|
KEGG ID | C02961 |
---|
UniProt ID | Not Available |
---|
OMIM ID | |
---|
ChEBI ID | 28680 |
---|
BioCyc ID | Not Available |
---|
CTD ID | D003561 |
---|
Stitch ID | Not Available |
---|
PDB ID | AR3 |
---|
ACToR ID | Not Available |
---|
Wikipedia Link | Cytarabine |
---|
References |
---|
Synthesis Reference | Michael Kluge, Herbert Schott, “Cytarabine derivatives, the preparation and use thereof.” U.S. Patent US5641758, issued August, 1992. |
---|
MSDS | T3D4978.pdf |
---|
General References | - 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. [166610 ]
- 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. [8229497 ]
- 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. [4038134 ]
- Bursztyn J, Boccara JF, Paillassou B, Bavoux F: [Corneal toxicity of cytarabine. Apropos of a case]. Ophtalmologie. 1989 Jun-Aug;3(3):229-30. [2641118 ]
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
|
---|
Gene Regulation |
---|
Up-Regulated Genes | Not Available |
---|
Down-Regulated Genes | Not Available |
---|