Chemical Component Summary

Name2-chloro-2'-deoxyadenosine
Identifiers(2R,3S,5R)-5-(6-amino-2-chloro-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
FormulaC10 H12 Cl N5 O3
Molecular Weight285.687
TypeNON-POLYMER
Isomeric SMILESc1nc2c(nc(nc2n1[C@H]3C[C@@H]([C@H](O3)CO)O)Cl)N
InChIInChI=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
InChIKeyPTOAARAWEBMLNO-KVQBGUIXSA-N

Chemical Details

Formal Charge0
Atom Count31
Chiral Atom Count3
Bond Count33
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB00242 
NameCladribine
Groups
  • approved
  • investigational
DescriptionAn antineoplastic agent used in the treatment of lymphoproliferative diseases including hairy-cell leukemia.
Synonyms
  • 2ClAdo
  • 2-Chlorodeoxyadenosine
  • 2-chloro-6-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
  • 2-chloro-deoxyadenosine
  • (2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Brand Names
  • Leustatin
  • Litak
  • Cladribine
  • Leustatin 1mg/ml
  • Cladribine Injection
IndicationFor the treatment of active hairy cell leukemia (leukemic reticuloendotheliosis) as defined by clinically significant anemia, neutropenia, thrombocytopenia, or disease-related symptoms. Also used as an alternative agent for the treatment of chronic lymphocytic leukemia (CLL), low-grade non-Hodgkin's lymphoma, and cutaneous T-cell lymphoma.
Categories
  • 2-Chloroadenosine
  • Agents Causing Muscle Toxicity
  • Antimetabolites
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
ATC-Code
  • L04AA40
  • L01BB04
CAS number4291-63-8

Drug Targets

NameTarget SequencePharmacological ActionActions
Ribonucleoside-diphosphate reductase large subunitMHVIKRDGRQERVMFDKITSRIQKLCYGLNMDFVDPAQITMKVIQGLYSG...unknowninhibitor
Ribonucleoside-diphosphate reductase subunit M2MLSLRVPLAPITDPQQLQLSPLKGLSLVDKENTPPALSGTRVLASKTARR...unknowninhibitor
Ribonucleoside-diphosphate reductase subunit M2 BMGDPERPEAAGLDQDERSSSDTNESEIKSNEEPLLRKSSRRFVIFPIQYP...unknowninhibitor
DNA-unknownother/unknown
DNA polymerase alpha catalytic subunitMAPVHGDDSLSDSGSFVSSRARREKKSKKGRQEALERLKKAKAGEKYKYE...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 20279
ChEMBL CHEMBL1619
ChEBI CHEBI:567361
CCDC/CSD IFOSAY