Ibudilast (CHEM020220)

Record Information
Version1.0
Creation Date2016-05-22 06:55:43 UTC
Update Date2026-08-19 06:25:27 UTC
Accession NumberCHEM020220
Identification
Common NameIbudilast
ClassSmall Molecule
Description
Ibudilast is an anti-inflammatory and neuroprotective oral agent which shows an excellent safety profile at 60 mg/day and provides significantly prolonged time-to-first relapse and attenuated brain volume shrinkage in patients with relapsing-remitting (RR) and/or secondary progressive (SP) multiple sclerosis (MS). Ibudilast is currently in development in the U.S. (codes: Ibudilast or MN-166), but is approved for use as an antiinflammatory in Japan.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
KetasKegg
2-Isopropyl-3-isobutyrylpyrazolo(1,5-a)pyridineHMDB
3-Isobutyryl-2-isopropyl-pyrazolo(1,5-a)pyridineHMDB
3-Isobutyryl-2-isopropylpyrazolo(1,5-a)pyridineHMDB
3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridineHMDB
AV-411HMDB
EyevinalHMDB
I0157_sigmaHMDB
IbudilastumHMDB
Ke tasHMDB
Lopac-I-0157HMDB
MN-166HMDB
Tocris-1694HMDB
UNII-m0TTH61XC5HMDB
Chemical FormulaC14H18N2O
Average Molecular Mass230.306 g/mol
Monoisotopic Mass230.142 g/mol
CAS Registry Number50847-11-5
IUPAC Name2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one
Traditional Nameibudilast
SMILESCC(C)C(=O)C1=C2C=CC=CN2N=C1C(C)C
InChI IdentifierInChI=1S/C14H18N2O/c1-9(2)13-12(14(17)10(3)4)11-7-5-6-8-16(11)15-13/h5-10H,1-4H3
InChI KeyZJVFLBOZORBYFE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrazolopyridines. Pyrazolopyridines are compounds containing a pyrazolopyridine skeleton, which consists of a pyrazole fused to a pyridine. Pyrazole is 5-membered ring consisting of three carbon atoms and two adjacent nitrogen centers. Pyridine is a 6-membered ring with four carbon and one nitrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrazolopyridines
Sub ClassNot Available
Direct ParentPyrazolopyridines
Alternative Parents
Substituents
  • Pyrazolopyridine
  • Aryl alkyl ketone
  • Aryl ketone
  • Pyridine
  • Azole
  • Pyrazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Ketone
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.18 g/LALOGPS
logP3.36ALOGPS
logP3.68ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)16.12ChemAxon
pKa (Strongest Basic)1.86ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.38 m³·mol⁻¹ChemAxon
Polarizability26.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB05266
HMDB IDHMDB0015614
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkIbudilast
Chemspider ID3543
ChEBI ID123745
PubChem Compound ID3671
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cho Y, Crichlow GV, Vermeire JJ, Leng L, Du X, Hodsdon ME, Bucala R, Cappello M, Gross M, Gaeta F, Johnson K, Lolis EJ: Allosteric inhibition of macrophage migration inhibitory factor revealed by ibudilast. Proc Natl Acad Sci U S A. 2010 Jun 22;107(25):11313-8. doi: 10.1073/pnas.1002716107. Epub 2010 Jun 8.
2. Rodgers KM, Bercum FM, McCallum DL, Rudy JW, Frey LC, Johnson KW, Watkins LR, Barth DS: Acute neuroimmune modulation attenuates the development of anxiety-like freezing behavior in an animal model of traumatic brain injury. J Neurotrauma. 2012 Jul 1;29(10):1886-97. doi: 10.1089/neu.2011.2273. Epub 2012 Apr 26.
3. Snider SE, Hendrick ES, Beardsley PM: Glial cell modulators attenuate methamphetamine self-administration in the rat. Eur J Pharmacol. 2013 Feb 15;701(1-3):124-30. doi: 10.1016/j.ejphar.2013.01.016. Epub 2013 Jan 31.