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Ibudilast

Ibudilast structure

CAS No:
50847-11-5
Formula:
C14H18N2O
Chemical Name:
Ibudilast
Synonyms:
1-Propanone,2-methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-;Pyrazolo[1,5-a]pyridine,1-propanone deriv.;2-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone;2-Isopropyl-3-isobutyrylpyrazolo[1,5-a]pyridine;KC 404;Ibudilast;Ketas;3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine;1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-one;AV 411;Pinatos;2-Methyl-1-(2-propan-2-ylpyrazolo[1,5-a]pyridin-3-yl)propan-1-one
Categories:
Active Pharmaceutical Ingredients > Antiallergic Drugs

Description

Ibudilast(KC-404;AV-411;MN-166) is a relatively nonselective phosphodiesterase inhibitor which has been marketed for treating asthma.Target: PDEIbudilast (3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine) is a nonselective inhibitor of cyclic nucleotide phosphodiesterase (PDE). The inhibition of platelet aggregation and vasodilatation by ibudilast may be due to synergistic elevation of intracellular cyclic nucleotides and release of nitric oxide (NO) or prostacyclin from endothelium, rath

Solid

Ibudilast is a pyrazolopyridine.|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: AV-411 or MN-166), but is approved for use as an antiinflammatory in Japan.|Ibudilast is an orally bioavailable inhibitor of cyclic nucleotide phosphodiesterase (PDE), mainly PDE-3, -4, -10, and -11, with anti-(neuro)inflammatory, vasorelaxant, bronchodilator, analgesic, neuroprotective and potential anti-tumor activities. Ibudilast (IBD) is able to cross the blood-brain barrier (BBB). Upon administration, IBD exerts its potential anti-tumor activity against glioblastoma multiforme (GBM) cells by inhibiting PDE-4 and the pro-inflammatory cytokine macrophage migration inhibitory factor (MIF), which results in a decrease in MIF, its receptor CD74, and AKT expression, and attenuates the immunosuppressive properties of monocytic myeloid-derived suppressor cells (MDSCs) and reduces T-regulatory cells (Tregs). This causes GBM cell apoptosis and inhibits GBM cell proliferation. In addition, IBD reduces, through its inhibitory effect on various PDEs, the production of certain pro-inflammatory cytokines, such as interleukin-6 (IL-6), IL- 1beta, leukotriene B4, and tumor necrosis factor-alpha (TNF-a). IBD also upregulates the anti-inflammatory cytokine (IL-10), and promotes the production of neurotrophic factors, such as brain-derived neurotrophic factor (BDNF), nerve growth factor (NGF), and neurotrophin-4 (NT-4). It also blocks toll-like receptor-4 (TLR-4), inhibits nitric oxide (NO) synthesis and reduces the level of reactive oxygen species (ROS). It also prevents platelet aggregation, causes cerebral vasodilation, bronchial smooth muscle relaxation, and improves cerebral blood flow. In addition, IBD attenuates the PDE-mediated activation of glial cells and abrogates PDE-mediated neuroinflammation and neurodegeneration. MIF is secreted by cancer stem cells (CSCs) and is highly expressed within GBM and plays a key role in tumor cell proliferation. Co-expression of MIF and CD74 in GBM is associated with poor patient survival.

Ibudilast Basic Attributes

Molecular Weight：

230.31

Exact Mass：

230.31

EC Number：

1806241-263-5

UNII：

M0TTH61XC5

DSSTox ID：

DTXSID7049007

NCI Thesaurus Code：

C65876

ATC Code：

R - Respiratory system

HScode：

2933990090

Characteristics

PSA：

34.4

XLogP3：

Appearance：

white solid

Density：

1.1±0.1 g/cm3

Melting Point：

53.5-54 °C

Boiling Point：

175°C/7.5mmHg(lit.)

Refractive Index：

1.571

Water Solubility：

DMSO: 28 mg/mL, soluble

Storage Conditions：

2-8°C

Toxicity：

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

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-36/37/38

safety instructions：

26-36

RTECS Number：

UR0711200

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H302-H315-H319-H335

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Toxicity Summary：

Neuroprotective role of phosphodiesterase inhibitor ibudilast on neuronal cell death induced by activated microglia

Drug Information

Drug Indication：

For the treatment of multiple sclerosis, asthma, and cerebrovascular disease.

MeSH：

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. (See all compounds classified as Platelet Aggregation Inhibitors.)|Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)|Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)

Biological Half-Life：

19 hours

Mechanism of Action：

Ibudilast 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.

MeSH Entry Terms：

3-isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine

Ibudilast Use and Manufacturing

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]

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:230.31
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:230.141913202
Monoisotopic Mass:230.141913202
Topological Polar Surface Area:34.4
Heavy Atom Count:17
Complexity:288
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

It has an inhibitory effect on the contraction of airway smooth muscle of isolated animals caused by inflammatory mediators such as leukotriene D4 (LTD4) and platelet activating factor (PAF); it can relieve airway smooth muscle spasm of guinea pigs caused by inflammatory mediators, and can inhibit passive skin allergic reactions in experimental animals.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Ibudilast sustained-release capsules
Ingredients	Main ingredients: The main ingredient of this product is ibudilast. Its chemical name is 2-methyl-1-[2-(1-methylethyl)pyrazolin[1,5-a]pyridin-3-yl]-1-propanone.
Indication	Not yet clear.
Specifications	10mg

Ibudilast extended-release tablets
Ingredients	The main ingredient of this product is ibudilast. Its chemical name is 2-methyl-1-[2-(1-methylethyl)pyrazolin[1,5-a]pyridin-3-yl]-1-propanone.
Indication	Not yet clear.
Specifications	10 mg
Manufacturer	Sichuan Yang Tian Biopharmaceutical Co., Ltd.

Ibudilast

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Registered Holders

Weihai Huaxi Pharmaceutical Group Co., Ltd.

China
Active
Gansu Haipunuo Ruichuang Pharmaceutical Co., Ltd.

China
Active
Shenzhen Neptunus Pharmaceutical Co., Ltd.

China
Active

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