Ibudilast

HCID 3671CAS 50847-11-5
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(C)C(=O)c1c(C(C)C)nn2ccccc12
InChIKey
ZJVFLBOZORBYFE-UHFFFAOYSA-N
Molecular formula
C14H18N2O
Average molar mass
230.31 g/mol
Monoisotopic mass
230.1419132

Overview

Ibudilast is a pyrazolopyridine.

Names & identifiers

Preferred name
Ibudilast
IUPAC
2-methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one
English name
Ibudilast
Molecular formula
C14H18N2O
Molecular weight
230.31

Names & synonyms

ibudilast50847-11-5KetasIbudilastumKC-404MN-166AV-4112-methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridineDTXSID7049007AV4113-Isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine
Show more names
CS-351PinatosEyevinalbudilastlbudilast
AV 411M0TTH61XC51-(2-Isopropylpyrazolo(1,5-a)pyridin-3-yl)-2-methyl-1-propanoneDTXCID20289332-methyl-1-(2-propan-2-ylpyrazolo(1,5-a)pyridin-3-yl)propan-1-oneMN166RefChem:789642R03DC04

Database identifiers

CAS
50847-11-5
PubChem CID
3671
DTXSID
DTXSID7049007
ChEMBL
CHEMBL19449
ChEBI
CHEBI:31684
UNII
M0TTH61XC5
EC Number
637-150-7
Nikkaji
J22.219D

Properties

Computed structural properties

XLogP
3
Topological polar surface area
34.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
3
Heavy atoms
17

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Solubility1.79e-01 g/L
Physical DescriptionSolid

Physicochemical properties

Melting point
53 · 53-54°C
Boiling point
175 °C/7.5mmHg · 175°C/7.5mmHg(lit.)
Density
1.09 · 1.09
refractive index
1.55 · 1.5500 (estimate)
storage temp.
2 · Sealed in dry,2-8°C
solubility
28 mg/mL, · DMSO: 28 mg/mL, soluble

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Ibudilast

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
UR0711200
hs_code
2933.99.8290
Toxicity
LD50 i.v. in mice: 260 mg/kg (Irikura, 1973)
risk_code
22-36/37/38

Chemistry & industry

Pharmacology

ATC Code · 2 items

R - Respiratory system

QR - Respiratory system

Mechanism of ActionIbudilast has mechanisms that include anti-inflammatory effects, such as phosphodiesterase inhibition, and neuroprotective effects, such as inhibition of [nitric oxide] synthesis and reduction in reactive oxygen species.
Biological Half-Life19 hours
MeSH Pharmacological Classification · 4 items

Agents that cause an increase in the expansion of a bronchus or bronchial tubes.

Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.

Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.

Drugs used to cause dilation of the blood vessels.

Cellular LocationsCytoplasm
Applications · 4 items

DescriptionIbudilast 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.

Usesa phosphodiesterase inhibitor with anti-inflammatory activity

UsesInhibitors 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]

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

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]

Additional notes

DefinitionChEBI: Ibudilast is a pyrazolopyridine.

Related reactions

15 records
New reaction record

Linked notes

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