Identification

Generic Name
Isatoribine
DrugBank Accession Number
DB04860
Background

Isatoribine is a selective agonist of TLR7.

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 316.29
Monoisotopic: 316.047754826
Chemical Formula
C10H12N4O6S
Synonyms
  • 7-Deaza-7-thia-8-oxoguanosine
  • 7-Thia-8-oxoguanosine
  • 7-TOG
  • Isatoribine
External IDs
  • ANA-245
  • ANA245
  • ICN-10146
  • NARI-10146

Pharmacology

Indication

For the treatment of Hepatitis C.

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Pharmacodynamics

Isatoribine is a compound that elevates levels of interferon-alpha and provides antiviral and antimetastatic activity in a variety of murine systems. Isatoribine interacts with a specific receptor, Toll-like receptor 7, or TLR7, that is present on certain immune system cells. The compound also has a promising toxicity profile in multiple species. As of February 2007 this drug was no longer listed on Anadys development pipeline.

Mechanism of action

Isatoribine is believed to act by a mechanism of action involving interaction with Toll-like receptor 7 (TLR7) and stimulation of the patient's own immune system, but the precise mechanism by which isatoribine reduced viral load is unknown (possible mechanisms include an antiviral effect, modulation of innate immunity, or enhancement of cellular responses).

TargetActionsOrganism
UToll-like receptor 7Not AvailableHumans
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
Isatoribine monohydrate85141ONN7O198832-38-1BZWQQOVSUSJJJO-QAGDRQIHSA-N
International/Other Brands
Immusine

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as glycosylamines. These are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Glycosylamines
Alternative Parents
Pentoses / Pyrimidones / Aminopyrimidines and derivatives / Vinylogous amides / Thiazoles / Tetrahydrofurans / Heteroaromatic compounds / Secondary alcohols / Oxacyclic compounds / Azacyclic compounds
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Substituents
Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Monosaccharide / N-glycosyl compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals
  • Hepatitis C virus, RSV and other RNA/DNA viruses

Chemical Identifiers

UNII
2DNT962H92
CAS number
122970-40-5
InChI Key
TZYVRXZQAWPIAB-FCLHUMLKSA-N
InChI
InChI=1S/C10H12N4O6S/c11-9-12-6-5(7(18)13-9)21-10(19)14(6)8-4(17)3(16)2(1-15)20-8/h2-4,8,15-17H,1H2,(H3,11,12,13,18)/t2-,3-,4-,8-/m1/s1
IUPAC Name
5-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2H,3H,4H,7H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione
SMILES
NC1=NC(=O)C2=C(N1)N([C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O)C(=O)S2

References

General References
  1. Horsmans Y, Berg T, Desager JP, Mueller T, Schott E, Fletcher SP, Steffy KR, Bauman LA, Kerr BM, Averett DR: Isatoribine, an agonist of TLR7, reduces plasma virus concentration in chronic hepatitis C infection. Hepatology. 2005 Sep;42(3):724-31. [Article]
  2. Fletcher S, Steffy K, Averett D: Masked oral prodrugs of toll-like receptor 7 agonists: a new approach for the treatment of infectious disease. Curr Opin Investig Drugs. 2006 Aug;7(8):702-8. [Article]
PubChem Compound
72231
PubChem Substance
175426870
ChemSpider
65192
ChEMBL
CHEMBL2105116
ZINC
ZINC000008214713

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility34.8 mg/mLALOGPS
logP-1.6ALOGPS
logP-2.6Chemaxon
logS-0.96ALOGPS
pKa (Strongest Acidic)11.81Chemaxon
pKa (Strongest Basic)3.15Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area157.71 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity78.7 m3·mol-1Chemaxon
Polarizability28.33 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8416
Blood Brain Barrier+0.825
Caco-2 permeable-0.7962
P-glycoprotein substrateNon-substrate0.6926
P-glycoprotein inhibitor INon-inhibitor0.969
P-glycoprotein inhibitor IINon-inhibitor0.9813
Renal organic cation transporterNon-inhibitor0.9501
CYP450 2C9 substrateNon-substrate0.7969
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateNon-substrate0.6253
CYP450 1A2 substrateNon-inhibitor0.795
CYP450 2C9 inhibitorNon-inhibitor0.8363
CYP450 2D6 inhibitorNon-inhibitor0.9405
CYP450 2C19 inhibitorNon-inhibitor0.8875
CYP450 3A4 inhibitorNon-inhibitor0.9506
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9783
Ames testNon AMES toxic0.6199
CarcinogenicityNon-carcinogens0.8624
BiodegradationNot ready biodegradable0.6954
Rat acute toxicity2.3196 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9951
hERG inhibition (predictor II)Non-inhibitor0.8547
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Key component of innate and adaptive immunity. TLRs (Toll-like receptors) control host immune response against pathogens through recognition of molecular patterns specific to microorganisms. TLR7 i...
Gene Name
TLR7
Uniprot ID
Q9NYK1
Uniprot Name
Toll-like receptor 7
Molecular Weight
120920.8 Da
References
  1. Horsmans Y, Berg T, Desager JP, Mueller T, Schott E, Fletcher SP, Steffy KR, Bauman LA, Kerr BM, Averett DR: Isatoribine, an agonist of TLR7, reduces plasma virus concentration in chronic hepatitis C infection. Hepatology. 2005 Sep;42(3):724-31. [Article]

Drug created at October 19, 2007 20:42 / Updated at February 21, 2021 18:51