| Identification | More | [Name]
Ibudilast | [CAS]
50847-11-5 | [Synonyms]
1-PROPANONE, 2-METHYL-1-[2-(1-METHYLETHYL)PYRAZOLO[1,5-A]PYRIDIN-3-YL]
2-isopropyl-3-isobutyrylpyrazolo[1,5-a]pyridine
2-METHYL-1-[2-(1-METHYLETHYL)PYRAZOLO[1,5-A]PYRIDIN-3-YL]-1-PROPANONE
3-ISOBUTYRYL-2-ISOPROPYLPYRAZOLO(1,5-A)PYRIDINE
IBUDILAST
IBUDILAST-D7
KC-404
2-methyl-1-(2-(1-methylethyl)pyrazolo(1,5-a)pyridin-3-yl)-1-propanon
5-a)pyridine,3-isobutyryl-2-isopropyl-pyrazolo(
lbudilast
2-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone, 3-isobutyrl-2-isopropylpyrazolo[1,5-a]pyridine, KC-404, Ketas
2-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-α]pyridin-3-yl]-1-propanone, 3-isobutyrl-2-isopropylpyrazolo[1,5-α]pyridine, KC-404, Ketas
3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine, KC-404, 2-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl] 1-propanone
3-Isobutyryl-2-isopropy-lpyrazolo[1，5-α]pyridine
Ketas
Eyevinal
1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methyl-1-propanone
Pinatos | [EINECS(EC#)]
637-150-7 | [Molecular Formula]
C14H18N2O | [MDL Number]
MFCD00864808 | [Molecular Weight]
230.31 | [MOL File]
50847-11-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
53-54°C | [Boiling point ]
175°C/7.5mmHg(lit.) | [density ]
1.09 | [refractive index ]
1.5500 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: 28 mg/mL, soluble
| [form ]
solid
| [pka]
1.22±0.30(Predicted) | [color ]
white
| [Usage]
A leukotriene D4 antagonist. Used as an antiallergic, antiasthmatic, and vasodilator (cerebral) | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
UR0711200
| [HS Code ]
2933.99.8290 | [Toxicity]
LD50 i.v. in mice: 260 mg/kg (Irikura, 1973) |
| Hazard Information | Back Directory | [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 leukotriene D4 antagonist. Used as an antiallergic, antiasthmatic, and vasodilator (cerebral) | [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] | [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 -20°C | [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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