NAV

Tetomilast

Identification

Generic Name
Tetomilast
DrugBank Accession Number
DB05298
Background

Tetomilast has been used in trials studying the treatment of Crohn Disease, Colitis, Ulcerative, and Chronic Obstructive Pulmonary Disease.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 370.422
Monoisotopic: 370.098727764
Chemical Formula
C19H18N2O4S
Synonyms
  • Tetomilast
External IDs
  • OPC-6535
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Pharmacology

Indication

Investigated for use/treatment in ulcerative colitis.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UcAMP-specific 3',5'-cyclic phosphodiesterase 4DNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyridinecarboxylic acids and derivatives
Direct Parent
Pyridinecarboxylic acids
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 2,4-disubstituted thiazoles / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 2 more
Substituents
2,4-disubstituted 1,3-thiazole / Alkyl aryl ether / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Ether / Heteroaromatic compound
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
S6RXB5KF56
CAS number
145739-56-6
InChI Key
XDBHURGONHZNJF-UHFFFAOYSA-N
InChI
InChI=1S/C19H18N2O4S/c1-3-24-16-9-8-12(10-17(16)25-4-2)18-21-15(11-26-18)13-6-5-7-14(20-13)19(22)23/h5-11H,3-4H2,1-2H3,(H,22,23)
IUPAC Name
6-[2-(3,4-diethoxyphenyl)-1,3-thiazol-4-yl]pyridine-2-carboxylic acid
SMILES
CCOC1=C(OCC)C=C(C=C1)C1=NC(=CS1)C1=NC(=CC=C1)C(O)=O

References

General References
  1. Bloomfield GL, Ridings PC, Blocher CR, Fisher BJ, Sugerman HJ, Nagamoto H, Fowler AA: OPC-6535, a superoxide anion production inhibitor, attenuates acute lung injury. J Surg Res. 1997 Sep;72(1):70-7. [Article]
PubChem Compound
3025803
PubChem Substance
175426973
ChemSpider
2291461
BindingDB
50035677
ChEMBL
CHEMBL332750
ZINC
ZINC000000600360

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentUlcerative Colitis3
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2TerminatedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2TerminatedTreatmentCrohn's Disease (CD)1
2TerminatedTreatmentUlcerative Colitis1

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
PropertyValueSource
Water Solubility0.00301 mg/mLALOGPS
logP4.38ALOGPS
logP4.3Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)0.8Chemaxon
pKa (Strongest Basic)4.17Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area81.54 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity107.91 m3·mol-1Chemaxon
Polarizability39.86 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9146
Blood Brain Barrier-0.5473
Caco-2 permeable-0.5594
P-glycoprotein substrateSubstrate0.5453
P-glycoprotein inhibitor INon-inhibitor0.8011
P-glycoprotein inhibitor IINon-inhibitor0.8762
Renal organic cation transporterNon-inhibitor0.8494
CYP450 2C9 substrateNon-substrate0.7883
CYP450 2D6 substrateNon-substrate0.8472
CYP450 3A4 substrateNon-substrate0.6292
CYP450 1A2 substrateInhibitor0.8337
CYP450 2C9 inhibitorInhibitor0.7282
CYP450 2D6 inhibitorNon-inhibitor0.8114
CYP450 2C19 inhibitorInhibitor0.6632
CYP450 3A4 inhibitorNon-inhibitor0.5747
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9381
Ames testNon AMES toxic0.6773
CarcinogenicityNon-carcinogens0.8916
BiodegradationNot ready biodegradable0.9768
Rat acute toxicity2.4193 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9971
hERG inhibition (predictor II)Non-inhibitor0.8183
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-d85db8e45d929d122173
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0098000000-4a6eb955c223fd909fa4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0umi-0009000000-97b079eada6686dfb371
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002b-0094000000-fa25b5dbc4babda19f26
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-0096000000-3846df2db4272fda4c23
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0293000000-4e692141a26ecd0d9293
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-208.9534416
predicted
DarkChem Lite v0.1.0
[M-H]-182.40668
predicted
DeepCCS 1.0 (2019)
[M+H]+209.7653416
predicted
DarkChem Lite v0.1.0
[M+H]+184.76468
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.5585416
predicted
DarkChem Lite v0.1.0
[M+Na]+192.38081
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. cAMP-specific 3',5'-cyclic phosphodiesterase 4D
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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

Drug created at November 18, 2007 18:23 / Updated at February 21, 2021 18:51