Ibudilast Chemical Properties

Melting point:

53-54°C

Boiling point:

175°C/7.5mmHg(lit.)

Density 

1.09

refractive index 

1.5500 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

DMSO: 28 mg/mL, soluble

form 

solid

pka

1.22±0.30(Predicted)

color 

white

Merck 

14,4879

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

InChI

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

InChIKey

ZJVFLBOZORBYFE-UHFFFAOYSA-N

SMILES

C(C1=C2N(N=C1C(C)C)C=CC=C2)(=O)C(C)C

CAS DataBase Reference

50847-11-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UR0711200

HS Code 

2933.99.8290

Toxicity

LD50 i.v. in mice: 260 mg/kg (Irikura, 1973)

MSDS

• Language:English Provider:2-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone
• Language:English Provider:SigmaAldrich

Ibudilast Usage And Synthesis

Description

Ibudilast is a leukomene antagonist and phosphodiesterase inhibitor useful in the treatment of bronchial asthma. It antagonizes leukotriene D4-induced contractions of guinea pig ileum and tracheal muscles in virro, and inhibits eosinophil accumulation in vivo.

Chemical Properties

White Solid

Originator

Kyorin (Japan)

Uses

a phosphodiesterase inhibitor with anti-inflammatory activity

Uses

Inhibitors of phosphodiesterase 4 (PDE4), which catalyzes the hydrolysis of cAMP, have potential applications in a variety of diseases, including asthma. Ibudilast is an inhibitor of PDE4 (IC50 = 54-239 nM) that, at higher doses, also inhibits PDE3 and PDE5 (IC50 = 1,600-3,510 nM). Through this action, it suppresses the elaboration of mediators involved in asthma and inflammation.[Cayman Chemical]

Uses

A leukotriene D4 antagonist. Used as an antiallergic, antiasthmatic, and vasodilator (cerebral)

Definition

ChEBI: Ibudilast is a pyrazolopyridine.

brand name

Ketas

Biological Activity

Phosphodiesterase inhibitor (IC 50 values are 53, 35, 48, 12 and 10 mM for PDE Ia, II, III, IV and V respectively). Inhibits platelet aggregation and is an orally-active cerebral vasodilator, bronchodilator and antiallergic agent.

Biochem/physiol Actions

Phosphodiesterase IV (PDE4) inhbitor. Inhibits platelet aggregation. Anti-asthma drug.

in vitro

ibudilast could potently inhibit purified human pde4a, 4b, 4c and 4d with ic50 values at 54, 65, 239 and 166 nm, respectively. ibudilast was also able to effectively block lps-induced tumor necrosis factor and n-formyl-metleu-phe-induced leukotriene b4 biosynthesis in human whole blood [1].

in vivo

rats received a daily oral administration of 10, 30 or 60 mg/kg ibudilast. results showed that in the vehicle-treated animals, white matter lesions and microglial activation occurred in the optic tract, internal capsule and corpus callosum. a low dose of ibudilast failed to suppress the white matter lesions and microglial activation, whereas a dose of either 30 or 60 mg/kg ibudilast ameliorated these lesions [2].

IC 50

54-239 nm

storage

Store at RT

References

1) Kishi et al. (2001), Ibudilast: a non-selective PDE inhibitor with multiple actions on blood cells and the vascular wall; Cardiovasc. Drug Rev., 19 215 2) Yamazaki et al. (2011), Ibudilast. A mixed PDE3/4 inhibitor, causes a selective and nitric oxide/cGMP-independent relaxation of the intracranial vertebrobasilar artery; Eur. J. Pharmacol., 650 605 3) Cueva Vargas et al. (2016), The glial cell modulator ibudilast attenuates neuroinflammation and enhances retinal ganglion cell viability in glaucoma through protein kinase A signaling.; Neurobiol. Dis., 93 156 4) Mizuno et al. (2004), Neuroprotective role of phosphodiesterase inhibitor ibudilast on neuronal cell death induced by activated microglia; Neuropharmacology, 46 404 5) Ledeboer et al. (2007), Ibudilast (AV-411). A class therapeutic candidate for neuropathic pain and opioid withdrawal syndromes; Expert. Opin. Investig. Drugs, 16 935

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