ContaminantDB: Ibudilast

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 06:55:43 UTC

Update Date

2016-11-09 01:16:09 UTC

Accession Number

CHEM020220

Identification

Common Name

Ibudilast

Class

Small 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 Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Ketas	Kegg
2-Isopropyl-3-isobutyrylpyrazolo(1,5-a)pyridine	HMDB
3-Isobutyryl-2-isopropyl-pyrazolo(1,5-a)pyridine	HMDB
3-Isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine	HMDB
3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine	HMDB
AV-411	HMDB
Eyevinal	HMDB
I0157_sigma	HMDB
Ibudilastum	HMDB
Ke tas	HMDB
Lopac-I-0157	HMDB
MN-166	HMDB
Tocris-1694	HMDB
UNII-m0TTH61XC5	HMDB

Chemical Formula

C₁₄H₁₈N₂O

Average Molecular Mass

230.306 g/mol

Monoisotopic Mass

230.142 g/mol

CAS Registry Number

50847-11-5

IUPAC Name

2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one

Traditional Name

ibudilast

SMILES

CC(C)C(=O)C1=C2C=CC=CN2N=C1C(C)C

InChI Identifier

InChI=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 Key

ZJVFLBOZORBYFE-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrazolopyridines

Sub Class

Not Available

Direct Parent

Pyrazolopyridines

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	3.36	ALOGPS
logP	3.68	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	16.12	ChemAxon
pKa (Strongest Basic)	1.86	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	26.31 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ko-9620000000-41b0ba218eb72a30b29c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-1900000000-857f6720dd17fb2547d1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000w-3910000000-7c4d5c86420e4e74cdb1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1490000000-e05398fd5b7ddcf160e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9330000000-8fca320ae4500967062f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9200000000-f809e94dd2a3af4982fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0190000000-29d8c7d8254601f09a23	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a6r-0940000000-91b751bd446800ac3fe4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btl-2920000000-e768231925a9299b5328	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-5a3d2f6ed0a80e005143	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-1190000000-8b174dc132cb6ac2651b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006w-2900000000-a9dd3e6970b4fcaffd46	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-aa5e22fd3aed8a7657c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-0890000000-6c7384878a8fa5c86666	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ke-0900000000-37e60538e4767bd87892	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB05266

HMDB ID

HMDB0015614

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not 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.

Ibudilast (CHEM020220)

Structure for CHEM020220: Ibudilast