CHEBI:567361 - cladribine

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ChEBI Name cladribine
ChEBI ID CHEBI:567361
Definition 2'-Deoxyadenosine in which the hydrogen at position 2 on the purine ring has been substituted by chlorine. It inhibits the synthesis and repair of DNA, particularly in lymphocytes and monocytes, and is used as an antimetabolite antineoplastic drug for the treatment of lymphoid malignancies including hairy-cell leukaemia and chronic lymphocytic leukaemia.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:568373, CHEBI:31407
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Formula C10H12ClN5O3
Net Charge 0
Average Mass 285.68700
Monoisotopic Mass 285.063
InChI InChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1
InChIKey PTOAARAWEBMLNO-KVQBGUIXSA-N
SMILES Nc1nc(Cl)nc2n(cnc12)[C@H]1C[C@H](O)[C@@H](CO)O1
Roles Classification
Biological Role(s): 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.
Application(s): 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.
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ChEBI Ontology
Outgoing cladribine (CHEBI:567361) has role antineoplastic agent (CHEBI:35610)
cladribine (CHEBI:567361) has role immunosuppressive agent (CHEBI:35705)
cladribine (CHEBI:567361) is a organochlorine compound (CHEBI:36683)
cladribine (CHEBI:567361) is a purine 2'-deoxyribonucleoside (CHEBI:19254)
IUPAC Name
2-chloro-2'-deoxyadenosine
INNs Sources
cladribina ChEBI
cladribine ChemIDplus
cladribinum ChEBI
Synonyms Sources
(2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol DrugBank
2-CdA ChemIDplus
2-chloro-2'-deoxy-β-adenosine ChemIDplus
2-chloro-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine ChEBI
2-chloro-deoxyadenosine ChEMBL
2-chlorodeoxyadenosine ChemIDplus
2ClAdo ChEBI
Cladribine KEGG COMPOUND
CldAdo ChEBI
Manual Xrefs Databases
667 DrugCentral
Cladribine Wikipedia
D01370 KEGG DRUG
DB00242 DrugBank
EP173059 Patent
LSM-5976 LINCS
US4760137 Patent
View more database links
Registry Numbers Types Sources
4291-63-8 CAS Registry Number KEGG DRUG
4291-63-8 CAS Registry Number ChemIDplus
624220 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
17526755 PubMed citation ChEMBL
18570408 PubMed citation ChEMBL
26024233 PubMed citation Europe PMC
Last Modified
22 February 2017