IBUDILAST

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H18N2O
Molecular Weight	230.3055
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C(=O)C1=C2C=CC=CN2N=C1C(C)C

InChI

InChIKey=ZJVFLBOZORBYFE-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C14H18N2O
Molecular Weight	230.3055
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607039
Curator's Comment: description was created based on several sources, including https://www.drugbank.ca/drugs/DB05266 | https://www.ncbi.nlm.nih.gov/pubmed/27501293

Ibudilast (KETAS®) is a non-selective cyclic nucleotide phosphodiesterase (PDE) inhibitor. It is an antithrombotic, antiasthmatic drug that is used for improving prognosis and relieving symptoms in patients suffering from ischemic stroke and for the treatment of bronchial asthma. A definitive mechanism of its action is yet to be established. However, inhibition of the release of inflammatory cytokines, inhibition of leukocyte activation, and inhibition of the expression of cell adhesion molecules have been proposed as likely mechanisms of action of ibudilast (KETAS®). It is currently in development in the US (for instance as a potential therapy for multiple sclerosis), but is approved for use in Japan.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphodiesterase 3A 7 Target ID: CHEMBL241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607039	Inhibitor 8504	9.5 µM [Ki]
Phosphodiesterase 4A 13 Target ID: CHEMBL254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607039	Inhibitor 8504	3.3 µM [Ki]
Phosphodiesterase 10A 13 Target ID: CHEMBL4409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607039	Inhibitor 8504	1.27 µM [Ki]
Phosphodiesterase 11A 3 Target ID: CHEMBL2717 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11607039	Inhibitor 8504	8.9 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchial asthma 50 Sources: http://www.kyorin-pharm.co.jp/prodinfo/medicine/pdf/KETAS_Capsules.pdf	Primary		Approved 8583	KETAS Approved Use 1. Bronchial asthma 2. Improvement of dizziness secondary to chronic cerebral circulation impairment associated with sequelae of cerebral infarction
Cerebral infarction 14 Sources: http://www.kyorin-pharm.co.jp/prodinfo/medicine/pdf/KETAS_Capsules.pdf	Palliative		Approved 8583	KETAS Approved Use 1. Bronchial asthma 2. Improvement of dizziness secondary to chronic cerebral circulation impairment associated with sequelae of cerebral infarction

C_max

Value	Dose	Analyte	Population
32 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
59.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg 2 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
59.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg 2 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
25 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/230109_4490010N1021_1_013_1F.pdf#PAGE=19	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
30 ng/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/230109_4490010N1021_1_013_1F.pdf#PAGE=19	10 mg 3 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	IBUDILAST blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19629961/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
373 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
517 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg 2 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
507 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg 2 times / day steady-state, oral dose: 30 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
334 ng × h/mL OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/230109_4490010N1021_1_013_1F.pdf#PAGE=19	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
118.44 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19629961/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
19.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19032723/	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
12 h OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/230109_4490010N1021_1_013_1F.pdf#PAGE=19	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST blood	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.76 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19629961/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	IBUDILAST serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% OTHER GOV'T http://www.info.pmda.go.jp/go/interview/1/230109_4490010N1021_1_013_1F.pdf#PAGE=20			IBUDILAST serum	Homo sapiens
0.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19925385/			IBUDILAST plasma	Homo sapiens population: age: sex: MALE food status:

Doses

Dose	Population	Adverse events
100 mg 2 times / day multiple, oral Highest studied dose Dose: 100 mg, 2 times / day Route: oral Route: multiple Dose: 100 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30157388/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30157388/	Other AEs: Abdominal pain, Diarrhea... Other AEs: Abdominal pain (5%) Diarrhea (16%) Nausea (27%) Vomiting (7%) Fatigue (11%) Skin infection (1%) Upper respiratory tract infection (10%) Urinary tract infection (27%) Back pain (8%) Pain in arm (4%) Pain in leg (4%) Headache (18%) Depression (9%) Insomnia (11%) Sources: https://pubmed.ncbi.nlm.nih.gov/30157388/
30 mg 2 times / day multiple, oral Studied dose Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/19032723/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/19032723/	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/19032723/

AEs

PubMed

Title	Date	PubMed
Phosphodiesterase inhibitors. Part 1: Synthesis and structure-activity relationships of pyrazolopyridine-pyridazinone PDE inhibitors developed from ibudilast.	2011-06-01	21530250
The glial cell modulator and phosphodiesterase inhibitor, AV411 (ibudilast), attenuates prime- and stress-induced methamphetamine relapse.	2010-07-10	20399770
Recent advances on phosphodiesterase 4 inhibitors for the treatment of asthma and chronic obstructive pulmonary disease.	2008-09-25	18686943
Phosphodiesterase inhibitors suppress IL-12 production with microglia and T helper 1 development.	2003-12	14664469
Ménière's disease in childhood.	2001-12-01	11700197
Ibudilast attenuates astrocyte apoptosis via cyclic GMP signalling pathway in an in vitro reperfusion model.	2001-07	11454657
Ibudilast: a non-selective PDE inhibitor with multiple actions on blood cells and the vascular wall.	2001	11607039

Patents

Sample Use Guides

In Vivo Use Guide

In case of bronchhial asthma: The usual adult dosage for oral use is 10 mg of ibudulast (KETAS®) twice daily. In case of cerebro-vascular disorders: The usual dosage for oral use is 10 mg of ibudulast (KETAS®) three times daily. The dosage may be adjusted according to the patient's symptoms.

Route of Administration: Oral

In Vitro Use Guide

The inhibitory effect of ibudilast against the human phosphodiesterase (PDE) enzyme family was measured. Ibudilast did not exhibit PDE4 subfamily selectivity with Ki values ranging from 3.3 uM to 6.3 uM. Inhibition of PDE10 by ibudilast was essentially the same with cAMP and cGMP as substrates yielding Ki values of 2.2 uM and 1.3 uM, respectively. PDE11 was tested for inhibition using both cAMP and cGMP substrates and cAMP hydrolysis was sensitive to inhibition with a Ki value of 8.9 uM. PDE3A was inhibited by ibudilast with a Ki of 9.5 uM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:03:39 GMT 2025` Edited by `admin` on `Mon Mar 31 18:03:39 GMT 2025`
Record UNII	M0TTH61XC5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

KETAS

Preferred Name

English

IBUDILAST

Official Name

English

AV-411

Code

English

IBUDILAST [MART.]

Common Name

English

AV411

Code

English

Ibudilast [WHO-DD]

Common Name

English

ibudilast [INN]

Common Name

English

1-(2-ISOPROPYLPYRAZOLO(1,5-.ALPHA.)PYRIDIN-3-YL)-2-METHYL-1-PROPANONE

Common Name

English

IBUDILAST [MI]

Common Name

English

MN-166

Code

English

IBUDILAST [JAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QR03DC04