Identification
- Generic Name
- Ibudilast
- DrugBank Accession Number
- DB05266
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Ibudilast (DB05266)
- Weight
- Average: 230.3055
Monoisotopic: 230.141913208 - Chemical Formula
- C14H18N2O
- Synonyms
- Ibudilast
- Ibudilastum
- External IDs
- AV-411
- AV411
- BRN 0656579
- MN-166
Pharmacology
- Indication
For the treatment of multiple sclerosis, asthma, and cerebrovascular disease.
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Not Available
- 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.
Target Actions Organism AcAMP-specific 3',5'-cyclic phosphodiesterase 4A inhibitorHumans AcAMP-specific 3',5'-cyclic phosphodiesterase 4B inhibitorHumans AcAMP-specific 3',5'-cyclic phosphodiesterase 4C inhibitorHumans UcAMP-specific 3',5'-cyclic phosphodiesterase 4D inhibitorHumans UcGMP-inhibited 3',5'-cyclic phosphodiesterase A inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
19 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Neuroprotective role of phosphodiesterase inhibitor ibudilast on neuronal cell death induced by activated microglia
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of hypotension can be increased when Ibudilast is combined with Abaloparatide. Abciximab The risk or severity of bleeding can be increased when Ibudilast is combined with Abciximab. Abrocitinib The risk or severity of bleeding and thrombocytopenia can be increased when Ibudilast is combined with Abrocitinib. Acebutolol Ibudilast may increase the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of bleeding can be increased when Aceclofenac is combined with Ibudilast. Acemetacin The risk or severity of bleeding can be increased when Acemetacin is combined with Ibudilast. Acenocoumarol The risk or severity of bleeding can be increased when Ibudilast is combined with Acenocoumarol. Acetylsalicylic acid Acetylsalicylic acid may increase the antiplatelet activities of Ibudilast. Alclofenac The risk or severity of bleeding can be increased when Alclofenac is combined with Ibudilast. Aldesleukin The risk or severity of bleeding can be increased when Ibudilast is combined with Aldesleukin. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Ke Tas / Ketas
Categories
- ATC Codes
- R03DC04 — Ibudilast
- Drug Categories
- Anti-Asthmatic Agents
- Antiplatelet agents
- Autonomic Agents
- Bronchodilator Agents
- Cardiovascular Agents
- Drugs for Obstructive Airway Diseases
- Enzyme Inhibitors
- Hematologic Agents
- Heterocyclic Compounds, Fused-Ring
- Leukotriene Antagonists
- Peripheral Nervous System Agents
- Phosphodiesterase 5 Inhibitors
- Phosphodiesterase Inhibitors
- Respiratory System Agents
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyrazolopyridines. These 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
- Aryl alkyl ketones / Pyridines and derivatives / Vinylogous amides / Pyrazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Ketone / Organic nitrogen compound / Organic oxide
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- M0TTH61XC5
- CAS number
- 50847-11-5
- InChI Key
- ZJVFLBOZORBYFE-UHFFFAOYSA-N
- 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
- IUPAC Name
- 2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one
- SMILES
- CC(C)C(=O)C1=C2C=CC=CN2N=C1C(C)C
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015614
- PubChem Compound
- 3671
- PubChem Substance
- 99443231
- ChemSpider
- 3543
- BindingDB
- 50240404
- ChEBI
- 31684
- ChEMBL
- CHEMBL19449
- ZINC
- ZINC000000004234
- PharmGKB
- PA165958351
- PDBe Ligand
- AVL
- Wikipedia
- Ibudilast
- PDB Entries
- 4grq
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Recruiting Treatment Myelopathy / Spinal Cord Diseases 1 2 Active Not Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Viral Pneumonia 1 2 Completed Basic Science Opioid Related Disorders 1 2 Completed Other Opioid Abuse / Opioid Dependence 1 2 Completed Treatment Alcohol Use Disorders (AUD) 2 2 Completed Treatment Amyotrophic Lateral Sclerosis (ALS) 1 2 Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Methamphetamine Dependence 1 2 Completed Treatment Primary Progressive Multiple Sclerosis (PPMS) / Secondary Progressive Multiple Sclerosis (SPMS) 1 2 Recruiting Treatment Alcohol Dependency / Alcohol Use Disorders (AUD) 1 2 Recruiting Treatment Methamphetamine Dependence 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.179 mg/mL ALOGPS logP 3.36 ALOGPS logP 3.68 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 16.55 Chemaxon pKa (Strongest Basic) 1.85 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 - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9868 Caco-2 permeable + 0.6112 P-glycoprotein substrate Non-substrate 0.788 P-glycoprotein inhibitor I Inhibitor 0.5207 P-glycoprotein inhibitor II Non-inhibitor 0.7071 Renal organic cation transporter Non-inhibitor 0.8179 CYP450 2C9 substrate Non-substrate 0.8076 CYP450 2D6 substrate Non-substrate 0.793 CYP450 3A4 substrate Substrate 0.5476 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.6259 CYP450 2C19 inhibitor Inhibitor 0.8071 CYP450 3A4 inhibitor Non-inhibitor 0.6338 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7965 Ames test Non AMES toxic 0.7408 Carcinogenicity Non-carcinogens 0.8482 Biodegradation Not ready biodegradable 0.9838 Rat acute toxicity 2.2040 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9554 hERG inhibition (predictor II) Non-inhibitor 0.9088
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-000w-3910000000-7c4d5c86420e4e74cdb1
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4A
- Uniprot ID
- P27815
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4A
- Molecular Weight
- 98142.155 Da
References
- Yagi K, Tada Y, Kitazato KT, Tamura T, Satomi J, Nagahiro S: Ibudilast inhibits cerebral aneurysms by down-regulating inflammation-related molecules in the vascular wall of rats. Neurosurgery. 2010 Mar;66(3):551-9; discussion 559. doi: 10.1227/01.NEU.0000365771.89576.77. [Article]
- Yamazaki T, Anraku T, Matsuzawa S: Ibudilast, a mixed PDE3/4 inhibitor, causes a selective and nitric oxide/cGMP-independent relaxation of the intracranial vertebrobasilar artery. Eur J Pharmacol. 2011 Jan 15;650(2-3):605-11. doi: 10.1016/j.ejphar.2010.10.033. Epub 2010 Oct 29. [Article]
- Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
- Gene Name
- PDE4B
- Uniprot ID
- Q07343
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4B
- Molecular Weight
- 83342.695 Da
References
- Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4C
- Uniprot ID
- Q08493
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4C
- Molecular Weight
- 79900.795 Da
References
- Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
- Gene Name
- PDE4D
- Uniprot ID
- Q08499
- Uniprot Name
- cAMP-specific 3',5'-cyclic phosphodiesterase 4D
- Molecular Weight
- 91114.1 Da
References
- Huang Z, Liu S, Zhang L, Salem M, Greig GM, Chan CC, Natsumeda Y, Noguchi K: Preferential inhibition of human phosphodiesterase 4 by ibudilast. Life Sci. 2006 May 1;78(23):2663-8. Epub 2005 Nov 28. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Metal ion binding
- Specific Function
- Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
- Gene Name
- PDE3A
- Uniprot ID
- Q14432
- Uniprot Name
- cGMP-inhibited 3',5'-cyclic phosphodiesterase A
- Molecular Weight
- 124978.06 Da
References
- Yamazaki T, Anraku T, Matsuzawa S: Ibudilast, a mixed PDE3/4 inhibitor, causes a selective and nitric oxide/cGMP-independent relaxation of the intracranial vertebrobasilar artery. Eur J Pharmacol. 2011 Jan 15;650(2-3):605-11. doi: 10.1016/j.ejphar.2010.10.033. Epub 2010 Oct 29. [Article]
Drug created at November 18, 2007 18:22 / Updated at January 14, 2023 19:02