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Forodesine

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Identification

Generic Name
Forodesine
DrugBank Accession Number
DB06185
Background

Forodesine 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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 266.2533
Monoisotopic: 266.101504956
Chemical Formula
C11H14N4O4
Synonyms
  • (1S)-1,4-dideoxy-4-imino-(9-deazahypoxanthin-9-yl)-D-ribitol
  • 1,4-Dideoxy-4-aza-1-(S)-(9-deazahypoxanthin-9-yl)-D-ribitol
  • Forodesine
  • Immucillin H
  • Immucillin-H
External IDs
  • BCX-1777
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Pharmacology

Indication

Investigated for use/treatment in lymphoma (non-hodgkin's) and leukemia (lymphoid).

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
APurine nucleoside phosphorylase
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Forodesine hydrochloride6SN82Y9U73284490-13-7WEIAMZKHBCLFOG-QPAIBFMUSA-N
International/Other Brands
Fodosine / Mundesine

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolopyrimidines
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidines
Alternative Parents
Pyrimidones / Aralkylamines / Substituted pyrroles / Vinylogous amides / Pyrrolidines / Heteroaromatic compounds / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Azacyclic compounds
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Substituents
1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dihydroxypyrrolidine, pyrrolopyrimidine (CHEBI:43362)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
426X066ELK
CAS number
209799-67-7
InChI Key
IWKXDMQDITUYRK-KUBHLMPHSA-N
InChI
InChI=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
IUPAC Name
7-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]-3H,4H,5H-pyrrolo[3,2-d]pyrimidin-4-one
SMILES
OC[C@H]1N[C@H]([C@H](O)[C@@H]1O)C1=CNC2=C1N=CNC2=O

References

General References
  1. Galmarini CM: Drug evaluation: forodesine - PNP inhibitor for the treatment of leukemia, lymphoma and solid tumor. IDrugs. 2006 Oct;9(10):712-22. [Article]
KEGG Drug
D06596
PubChem Compound
444499
ChemSpider
392417
BindingDB
50195587
ChEBI
43362
ChEMBL
CHEMBL218291
ZINC
ZINC000013492899
PDBe Ligand
IMH
Wikipedia
Forodesine
PDB Entries
1b8o / 1g2o / 1nw4 / 1pf7 / 1rr6 / 1rt9 / 2ff1 / 2ff2 / 2oc4 / 2oc9 …
show 11 more

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Unlock 175K+ rows when you subscribe.View sample data
2CompletedTreatmentChronic Lymphocytic Leukemia2somestatusstop reasonjust information to hide
2CompletedTreatmentCutaneous T-Cell Lymphoma (CTCL)1somestatusstop reasonjust information to hide
2CompletedTreatmentT Cell Leukemia1somestatusstop reasonjust information to hide
2TerminatedTreatmentLeukemias / Lymphoma1somestatusstop reasonjust information to hide
1CompletedTreatmentCancer1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.11 mg/mLALOGPS
logP-1.8ALOGPS
logP-2.7Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.03Chemaxon
pKa (Strongest Basic)7.94Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area129.97 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity66.37 m3·mol-1Chemaxon
Polarizability25.81 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9784
Blood Brain Barrier-0.7642
Caco-2 permeable-0.8425
P-glycoprotein substrateSubstrate0.5108
P-glycoprotein inhibitor INon-inhibitor0.9882
P-glycoprotein inhibitor IINon-inhibitor0.9682
Renal organic cation transporterNon-inhibitor0.9062
CYP450 2C9 substrateNon-substrate0.8181
CYP450 2D6 substrateNon-substrate0.7955
CYP450 3A4 substrateNon-substrate0.5742
CYP450 1A2 substrateNon-inhibitor0.7907
CYP450 2C9 inhibitorNon-inhibitor0.9242
CYP450 2D6 inhibitorNon-inhibitor0.9001
CYP450 2C19 inhibitorNon-inhibitor0.9373
CYP450 3A4 inhibitorNon-inhibitor0.8658
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8575
Ames testNon AMES toxic0.7612
CarcinogenicityNon-carcinogens0.9209
BiodegradationNot ready biodegradable0.8571
Rat acute toxicity2.0847 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.992
hERG inhibition (predictor II)Non-inhibitor0.9018
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4r-1290000000-ce341467973c983fd88f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-6fb23e36fd2c59008bdb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0190000000-118fdb60aac4242bf132
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-015j-0490000000-e96c2d0ca39251502bc6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2950000000-4f3578e025325bc4515a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-06uu-3930000000-7582a28c536c304a8139
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-8d7321aa3db5e125eaae
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-151.55513
predicted
DeepCCS 1.0 (2019)
[M+H]+153.9507
predicted
DeepCCS 1.0 (2019)
[M+Na]+160.65883
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Purine nucleoside phosphorylase
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Catalyzes the phosphorolytic breakdown of the N-glycosidic bond in the beta-(deoxy)ribonucleoside molecules, with the formation of the corresponding free purine bases and pentose-1-phosphate (PubMed:23438750, PubMed:9305964). Preferentially acts on 6-oxopurine nucleosides including inosine and guanosine (PubMed:9305964)
Specific Function
guanosine phosphorylase activity
Gene Name
PNP
Uniprot ID
P00491
Uniprot Name
Purine nucleoside phosphorylase
Molecular Weight
32117.69 Da
References
  1. Furman RR, Hoelzer D: Purine nucleoside phosphorylase inhibition as a novel therapeutic approach for B-cell lymphoid malignancies. Semin Oncol. 2007 Dec;34(6 Suppl 5):S29-34. [Article]
  2. Gore L, Stelljes M, Quinones R: Forodesine treatment and post-transplant graft-versus-host disease in two patients with acute leukemia: facilitation of graft-versus-leukemia effect? Semin Oncol. 2007 Dec;34(6 Suppl 5):S35-9. [Article]
  3. Gandhi V, Kilpatrick JM, Plunkett W, Ayres M, Harman L, Du M, Bantia S, Davisson J, Wierda WG, Faderl S, Kantarjian H, Thomas D: A proof-of-principle pharmacokinetic, pharmacodynamic, and clinical study with purine nucleoside phosphorylase inhibitor immucillin-H (BCX-1777, forodesine). Blood. 2005 Dec 15;106(13):4253-60. Epub 2005 Aug 30. [Article]
  4. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at March 19, 2008 16:16 / Updated at August 26, 2024 19:23