IMH

1,4-DIDEOXY-4-AZA-1-(S)-(9-DEAZAHYPOXANTHIN-9-YL)-D-RIBITOL


Toggle HydrogenToggle Labels

Chemical Component Summary

Name1,4-DIDEOXY-4-AZA-1-(S)-(9-DEAZAHYPOXANTHIN-9-YL)-D-RIBITOL
SynonymsForodesine; Immucillin H
Identifiers7-[(2~{S},3~{S},4~{R},5~{R})-5-(hydroxymethyl)-3,4-bis(oxidanyl)pyrrolidin-2-yl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
FormulaC11 H14 N4 O4
Molecular Weight266.253
TypeNON-POLYMER
Isomeric SMILESc1c(c2c([nH]1)C(=O)NC=N2)[C@H]3[C@@H]([C@@H]([C@H](N3)CO)O)O
InChIInChI=1S/C11H14N4O4/c16-2-5-9(17)10(18)7(15-5)4-1-12-8-6(4)13-3-14-11(8)19/h1,3,5,7,9-10,12,15-18H,2H2,(H,13,14,19)/t5-,7+,9-,10+/m1/s1
InChIKeyIWKXDMQDITUYRK-KUBHLMPHSA-N

Chemical Details

Formal Charge0
Atom Count33
Chiral Atom Count4
Bond Count35
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB06185 
NameForodesine
Groups investigational
DescriptionForodesine is a highly potent, orally active, rationally designed PNP inhibitor that has shown activity in preclinical studies with malignant cells and clinical utility against T-cell acute lymphoblastic leukemia and cutaneous T-cell lymphoma. Additional preliminary findings support its use for the management of some B-cell malignancies.
Synonyms
  • Forodesine hydrochloride
  • 1,4-Dideoxy-4-aza-1-(S)-(9-deazahypoxanthin-9-yl)-D-ribitol
  • Forodesine
  • Immucillin H
  • Immucillin-H
IndicationInvestigated for use/treatment in lymphoma (non-hodgkin's) and leukemia (lymphoid).
Categories
  • Heterocyclic Compounds, Fused-Ring
  • Nucleic Acids, Nucleotides, and Nucleosides
  • Nucleosides
  • Purine-Nucleoside Phosphorylase, antagonists & inhibitors
  • Purines
CAS number209799-67-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Purine nucleoside phosphorylaseMENGYTYEDYKNTAEWLLSHTKHRPQVAIICGSGLGGLTDKLTQAQIFDY...unknown
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
Pharos CHEMBL218291
PubChem 135409409, 5288627, 444499
ChEMBL CHEMBL218291
ChEBI CHEBI:43362