Compound: Forodesine
SMILES: O=c1[nH]cnc2c1[nH]cc2[C@@H]3N[C@H](CO)[C@H]([C@H]3O)O
InChIKey: IWKXDMQDITUYRK-KUBHLMPHSA-N
Synonyms: Forodesine, 209799-67-7, Immucillin H, Fodosine, Immucillin-H, mundesine, BCX-1777, ImmH cpd, 1,4-dideoxy-4-aza-1-(s)-(9-deazahypoxanthin-9-yl)-d-ribitol, Forodesina, 426X066ELK, (1S)-1,4-dideoxy-4-imino-(9-deazahypoxanthin-9-yl)-D-ribitol, NSC-717904, 1-(9-deazahypoxanthin-9-yl)-1,4-dideoxy-1,4-iminoribitol, CHEBI:43362, DTXSID50943276, 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one, 4H-Pyrrolo(3,2-d)pyrimidin-4-one, 7-((2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl)-1,5-dihydro-, forodesinum, 7-((2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-1,5-dihydro-4H-pyrrolo(3,2-d)pyrimidin-4-one, 7-((2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-1,5-dihydropyrrolo(2,3-e)pyrimidin-4-one, 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,5-dihydropyrrolo[2,3-e]pyrimidin-4-one, RefChem:600335, DTXCID101478471, BCX1777, MFCD09837827, 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,5-dihydropyrrolo[3,2-d]pyrimidin-4-one, CHEMBL218291, 5(S),12(S)-diHETE, 4H-Pyrrolo[3,2-d]pyrimidin-4-one, 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-pyrrolidinyl]-3,5-dihydro-, IMH, 2-Furoyl Ecgonine Methyl Ester, Fodosine (TN), 188948-53-0, 7-((2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one, 7-((2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one, 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one, Forodesine (USAN/INN), (-)-7-((2S,3S,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl)-1,5-dihydro-4H-pyrrolo(3,2-d)pyrimidin-4-one, (-)-7-[(2S,3S,4R,5R)-3,4-Dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-1,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one, (1R,2R,3S,5S)-Methyl 3-((furan-2-carbonyl)oxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, 7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one, 1b8o, 1g2o, 1nw4, 2ff1, 2ff2, FORODESINE [MI], FORODESINE [INN], Forodesine; Immucillin H, Forodesine [USAN:INN], FORODESINE [USAN], FORODESINE [WHO-DD], SCHEMBL506383, UNII-426X066ELK, Fodosine (proposed trade name), GTPL8272, orb1707303, SCHEMBL3896676, SCHEMBL16321929, SCHEMBL30989336, EX-A7842M, TXFGPFIDYBMMJY-KUBHLMPHSA-N, GLXC-07600, BCX 1777, BDBM50195587, AKOS027326672, AKOS040741759, CS-3781, DB06185, MD11591, NSC 717904, NCGC00485883-01, (2R,3R,4S,5S)-2-(hydroxymethyl)-5-(4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)pyrrolidine-3,4-diol, AS-35282, DA-53379, HY-16210, NS00070855, D06596, Q410040, BRD-K16505263-003-01-1, BRD-K16505263-003-02-9, (1S)-1,4-dideoxy-1-c-(4-hydroxypyrrolo[3,2-d]pyrimidin-7-yl)-1,4-imino-d-ribitol, 7-[(2s,3s,4r,5r)-3,4-dihydroxy-5-hydroxymethyl-2-pyrrolidinyl]-1,5-dihydro-4h-pyrrolo-[3,2-d]-pyrimidin-4-one
Theoretical properties:
molecular_formula: C11H14N4O4
molecular_weight: 266.25 g/mol
exact_mass: 266.10150494 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 2
heavy_atom_count: 19
topological_polar_surface_area: 130 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Immucillin H is a pyrrolopyrimidine and a dihydroxypyrrolidine.
chembl: FORODESINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Forodesine (INN; also known as Immucillin H; trade names Mundesine and Fodosine) is a transition-state analog inhibitor of purine nucleoside phosphorylase studied for the treatment of patients with T-cell acute lymphoblastic leukemia (T-ALL) and for treatment of B-cell acute lymphocytic leukemia (B-ALL).
Forodesine was originally discovered by Vern Schramm's laboratory at the Albert Einstein College of Medicine in New York and Industrial Research Limited in New Zealand.
Forodesine is being developed by BioCryst Pharmaceuticals. As of 2008, it is currently in phase II clinical trials..
In 2006, BioCryst entered into a licensing agreement with Mundipharma International Holdings Limited to develop and commercialize forodesine in markets across Europe, Asia, and Australasia for use in oncology.
In April 2017, forodesine was approved in Japan for the treatment of relapsed/refractory peripheral T-cell lymphoma.