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CHEBI:28680 - cytarabine

Default Structure
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:
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.
antiviral agent  A substance that destroys or inhibits replication of viruses.
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:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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
citarabinaChemIDplus
cytarabineWHO MedNet
cytarabineChemIDplus
cytarabinumChemIDplus
Synonyms  Source
1-beta-D-ArabinofuranosylcytosineChemIDplus
4-Amino-1-beta-D-arabinofuranosyl-2(1H)-pyrimidinoneChemIDplus
arabinocytosineDrugCentral
Arabinoside CDrugCentral
ara-CChEBI
CytarabineKEGG COMPOUND
Manual XrefsDatabases
770DrugCentral
AR3PDBeChem
C02961KEGG COMPOUND
CytarabineWikipedia
D00168KEGG DRUG
DB00987DrugBank
HMDB0015122HMDB
LSM-5470LINCS
Registry NumbersSources
Reaxys:89175Reaxys
CAS:147-94-4KEGG COMPOUND
CAS:147-94-4ChemIDplus
Citations