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CHEBI:28680 - cytarabine

ChEBI IDCHEBI:28680
ChEBI Namecytarabine
Stars
DefinitionA pyrimidine nucleoside in which cytosine is attached to D-arabinofuranose via a β-N1-glycosidic bond. Used mainly in the treatment of leukaemia, especially acute non-lymphoblastic leukaemia, cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. It also has antiviral and immunosuppressant properties.
Secondary ChEBI IDsCHEBI:4074, CHEBI:23532, CHEBI:40824
Last Modified20 June 2018
DownloadsMolfile
FormulaC9H13N3O5
Net Charge0
Average Mass243.219
Monoisotopic Mass243.08552
SMILESNc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1
InChIInChI=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
InChIKeyUHDGCWIWMRVCDJ-CCXZUQQUSA-N
Wikipedia
Roles Classification
Biological Roles:
antiviral agent  A substance that destroys or inhibits replication of viruses.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
antimetabolite  A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
immunosuppressive agent  An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response.
ChEBI Ontology
Outgoing Relation(s)
cytarabine (CHEBI:28680) has functional parent cytosine (CHEBI:16040)
cytarabine (CHEBI:28680) has role antimetabolite (CHEBI:35221)
cytarabine (CHEBI:28680) has role antineoplastic agent (CHEBI:35610)
cytarabine (CHEBI:28680) has role antiviral agent (CHEBI:22587)
cytarabine (CHEBI:28680) has role immunosuppressive agent (CHEBI:35705)
cytarabine (CHEBI:28680) is a monosaccharide derivative (CHEBI:63367)
cytarabine (CHEBI:28680) is a pyrimidine nucleoside (CHEBI:26440)
cytarabine (CHEBI:28680) is a β-D-arabinoside (CHEBI:38315)
IUPAC Name 
4-amino-1-β-D-arabinofuranosylpyrimidin-2(1H)-one
INNs  Source
cytarabineChemIDplus
cytarabinumChemIDplus
cytarabineWHO MedNet
citarabinaChemIDplus
Synonyms  Source
Cytosine arabinosideKEGG COMPOUND
CytarabineKEGG COMPOUND
Cytosine-1-beta-D-arabinofuranosideKEGG COMPOUND
1-beta-D-ArabinofuranosylcytosineChemIDplus
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinoneChemIDplus
cytosine-β-D-arabinofuranosideChEBI
Manual XrefsDatabases
C02961KEGG COMPOUND
AR3PDBeChem
CytarabineWikipedia
DB00987DrugBank
HMDB0015122HMDB
D00168KEGG DRUG
LSM-5470LINCS
770DrugCentral
Registry NumbersSources
Reaxys:89175Reaxys
CAS:147-94-4KEGG COMPOUND
CAS:147-94-4ChemIDplus
Citations