CAS 50847-11-5|3-isobutyryl-2-isopropylpyrazolo(1,5-a)pyridine|Ibudilastum|MN-166|I0157_SIGMA|Ketas|Ketas (TN)|Ibudilast [inn:jan]|Ke tas|3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine|UNII-M0TTH61...

General Information

Structure

Molecular Formula

C₁₄H₁₈N₂O

Molecular Mass

230.30552

Exact Mass

230.14191321

Charge

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

Canonic Smiles

CC(C(=O)c1c(nn2c1cccc2)C(C)C)C

Isomeric Smiles

O=C(c1c(nn2c1cccc2)C(C)C)C(C)C

Calculated Properties

JChem

Acid pKa

16.124111

H Acceptors

H Donor

LogD (pH = 5.5)

3.6791465

LogD (pH = 7.4)

3.6792438

Log P

3.679245

Molar Refractivity

79.375

Polarizability

26.83163

Polar Surface Area

34.37

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.36

LOG S

-3.11

Solubility (Water)

1.79e-01 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

IbudilastumKetas (TN)MN-166Ibudilast [inn:jan]3-Isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine3-isobutyryl-2-isopropylpyrazolo(1,5-a)pyridineKe tasKetasI0157_SIGMAUNII-M0TTH61XC5Tocris-1694Lopac-I-0157Pyrazolo(1,5-a)pyridine, 3-isobutyryl-2-isopropyl-Ibudilast (jan/inn)AV-4112-Isopropyl-3-isobutyrylpyrazolo(1,5-a)pyridineEyevinalIbudilastum [latin]IbudilastKC-4042-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl] 1-propanoneIbudilastAV 4112-Methyl-1-[2-(1-methylethyl)pyrazolo[1,5-a]pyridin-3-yl]-1-propanone1-(2-Isopropylpyrazolo[1,5-a]pyridin-3-yl)-2-methylpropan-1-oneKC 4042-Isopropyl-3-isobutyrylpyrazolo[1,5-a]pyridine

IUPAC name

2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one

IUPAC Traditional name

ketas ibudilast 2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one

Names and Identifiers

Registration numbers

CAS Number

50847-11-5

PubChem CID

3671

PubChem SID

1609678439944323124278482

MDL Number

MFCD00864808

Registration numbers

Properties

Safety Information

22-36/37/38

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

human ... PDE4A(5141), PDE4B(5142), PDE4C(5143), PDE4D(5144)

Bronchodilator

Lowers Ca 2+ deposition in soft tissues

Phosphodiesterase inhibitor

Vasodilator

Properties

Related Proteins

No Data Available

Click here to submit data

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB05266

Drug Groups

approved; investigational

Description

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.

Indication

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

Toxicity

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

Affected Organisms

Humans and other mammals

Half Life

19 hours

External Links

• [Wikipedia]

Sigma Aldrich

I0157

Biochem/physiol Actions
Phosphodiesterase IV (PDE4) inhbitor. Inhibits platelet aggregation. Anti-asthma drug.

TRC

I125000

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

Molecule Details

References

PubChem Literature

From Data Sources

• Nishino, K., et al.: Japan J. Pharmacol., 33, 267 (1983)

• Ohashi, M., et al.: Arch. Int. Pharmacodyn., 280, 216 (1983)

• Armstead, W.M., et al.: J. Pharmacol., Exp. Ther., 244, 138 (1983)

• Yasui, M. et al., J. Int. Med. Res., 1990, 18, 415, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1140

• Nagai, H. et al., Jpn. J. Pharmacol., 1983, 33, 1215, (pharmacol)

• Izumi, Y. et al., Arzneim.-Forsch., 1990, 40, 1300

• Ohashi, M. et al., Int. Arch. Allergy Appl. Immunol., 1993, 101, 288, (pharmacol)

• Souness, J.E. et al., Br. J. Pharmacol., 1994, 111, 1081, (pharmacol)

• Japan. Pat., 1977, Kyorin Pharm, 77 14 799; CA, 87, 53282w, (synth, pharmacol)

• Ger. Pat., 1973, Kyorin Pharm, 2 315 801; CA, 80, 14923s, (synth)

• Mue, S. et al., Arch. Int. Pharmacodyn. Ther., 1986, 283, 153, (pharmacol)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one

IUPAC Traditional name

ketas ibudilast 2-methyl-1-[2-(propan-2-yl)pyrazolo[1,5-a]pyridin-3-yl]propan-1-one

Properties

Safety Information

22-36/37/38

Acute toxicity (oral, dermal, inhalation), category 4

Skin irritation, category 2

Eye irritation, category 2

Skin sensitisation, category 1

Specific Target Organ Toxicity – Single exposure, category 3

Pharmacology Properties

human ... PDE4A(5141), PDE4B(5142), PDE4C(5143), PDE4D(5144)

Bronchodilator

Lowers Ca 2+ deposition in soft tissues

Phosphodiesterase inhibitor

Vasodilator

Molecule Details

DrugBank

DB05266

Drug Groups

approved; investigational

Description

Indication

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

Toxicity

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

Affected Organisms

Humans and other mammals

Half Life

19 hours

External Links

• [Wikipedia]

Sigma Aldrich

I0157

Biochem/physiol Actions
Phosphodiesterase IV (PDE4) inhbitor. Inhibits platelet aggregation. Anti-asthma drug.

TRC

I125000

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

Data Source

Academic Data

Commercial Catalog

Bioactivity

PubChem BioAssay

References

PubChem Literature

From Data Sources

• Nishino, K., et al.: Japan J. Pharmacol., 33, 267 (1983)

• Ohashi, M., et al.: Arch. Int. Pharmacodyn., 280, 216 (1983)

• Armstead, W.M., et al.: J. Pharmacol., Exp. Ther., 244, 138 (1983)

• Yasui, M. et al., J. Int. Med. Res., 1990, 18, 415, (pharmacol)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1140

• Nagai, H. et al., Jpn. J. Pharmacol., 1983, 33, 1215, (pharmacol)

• Izumi, Y. et al., Arzneim.-Forsch., 1990, 40, 1300

• Ohashi, M. et al., Int. Arch. Allergy Appl. Immunol., 1993, 101, 288, (pharmacol)

• Souness, J.E. et al., Br. J. Pharmacol., 1994, 111, 1081, (pharmacol)

• Japan. Pat., 1977, Kyorin Pharm, 77 14 799; CA, 87, 53282w, (synth, pharmacol)

• Ger. Pat., 1973, Kyorin Pharm, 2 315 801; CA, 80, 14923s, (synth)

• Mue, S. et al., Arch. Int. Pharmacodyn. Ther., 1986, 283, 153, (pharmacol)

Registration numbers

CAS Number

50847-11-5

PubChem CID

3671

PubChem SID

1609678439944323124278482

MDL Number

MFCD00864808

Related Proteins

No Data Available

Click here to submit data

Molecule

ID:4411