NAV

Dilmapimod

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Dilmapimod
DrugBank Accession Number
DB12140
Background

Dilmapimod has been used in trials studying the treatment and diagnostic of Nerve Trauma, Inflammation, Pain, Neuropathic, Arthritis, Rheumatoid, and Coronary Heart Disease, among others. Dilmapimod (SB-681323) is a p38 MAP-kinase inhibitor that has potential uses in inflammatory conditions such as RA (Rheumatoid Arthritis). Previous p38 MAP-kinase inhibitors have been hindered in development by liver toxicity. Methotrexate (common treatment for RA patients) also has potential liver toxicity.}

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 456.425
Monoisotopic: 456.140924977
Chemical Formula
C23H19F3N4O3
Synonyms
  • Dilmapimod
External IDs
  • SB-681323
  • SB681323
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Pharmacology

Indication

Dilmapimod has been used in trials studying the treatment and diagnostic of Nerve Trauma, Inflammation, Pain, Neuropathic, Arthritis, Rheumatoid, and Coronary Heart Disease, among others.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Dilmapimod reduces the levels of proinflammatory cytokines and chemokines and reduce cellular infiltration to sites of inflammation, thereby reducing local damage. In diseases such as RA and IBD, TNFα blockade through either anti-TNFα antibodies or use of soluble TNFα receptors. Inhibition of p38α offers significant inhibition of TNFα, and cytokines such as IL-1β and IL-6, which offer additional therapeutic efficacy.

TargetActionsOrganism
UTumor necrosis factorNot AvailableHumans
UInterleukin-1 betaNot AvailableHumans
UInterleukin-6Not 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

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dilmapimod tosylate7R1193W65J937169-00-1ONQKJJNSLLVYHF-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpyrimidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrimidine ring through a CC or CN bond. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Phenylpyrimidines
Alternative Parents
Pyrido[2,3-d]pyrimidines / Toluenes / Pyridinones / Fluorobenzenes / Aminopyrimidines and derivatives / Aryl fluorides / Heteroaromatic compounds / Lactams / Azacyclic compounds / Primary alcohols
show 4 more
Substituents
4-phenylpyrimidine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Fluorobenzene
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Q3238VQW0N
CAS number
444606-18-2
InChI Key
ORVNHOYNEHYKJG-UHFFFAOYSA-N
InChI
InChI=1S/C23H19F3N4O3/c1-12-9-13(24)5-6-15(12)20-16-7-8-19(33)30(21-17(25)3-2-4-18(21)26)22(16)29-23(28-20)27-14(10-31)11-32/h2-9,14,31-32H,10-11H2,1H3,(H,27,28,29)
IUPAC Name
8-(2,6-difluorophenyl)-2-[(1,3-dihydroxypropan-2-yl)amino]-4-(4-fluoro-2-methylphenyl)-7H,8H-pyrido[2,3-d]pyrimidin-7-one
SMILES
CC1=CC(F)=CC=C1C1=C2C=CC(=O)N(C2=NC(NC(CO)CO)=N1)C1=C(F)C=CC=C1F

References

General References
  1. Hollenbach E, Neumann M, Vieth M, Roessner A, Malfertheiner P, Naumann M: Inhibition of p38 MAP kinase- and RICK/NF-kappaB-signaling suppresses inflammatory bowel disease. FASEB J. 2004 Oct;18(13):1550-2. Epub 2004 Aug 2. [Article]
  2. Schindler JF, Monahan JB, Smith WG: p38 pathway kinases as anti-inflammatory drug targets. J Dent Res. 2007 Sep;86(9):800-11. [Article]
PubChem Compound
10297982
PubChem Substance
347828437
ChemSpider
8473450
ChEMBL
CHEMBL2103838
ZINC
ZINC000034997404

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
2CompletedTreatmentCoronary Heart Disease (CHD)1
2CompletedTreatmentLung Injury, Acute (ALI)1
2CompletedTreatmentNeuropathic Pain1
2CompletedTreatmentRheumatoid Arthritis2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0118 mg/mLALOGPS
logP3.03ALOGPS
logP3.6Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)13.38Chemaxon
pKa (Strongest Basic)1.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area98.58 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity118 m3·mol-1Chemaxon
Polarizability43.31 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0000900000-2bebc9b76ce7453b0293
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aor-3006900000-2c8b07ddb875e5bd81a9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0000900000-3f30d4de6c3de56f574f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0001900000-0ee0bd4481f6637220a0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-08gi-0019200000-f0ad57276959b845f35e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-1029600000-bbc5f66b98e571832721
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]-196.28072
predicted
DeepCCS 1.0 (2019)
[M+H]+198.63872
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.77766
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Tumor necrosis factor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tumor necrosis factor receptor binding
Specific Function
Cytokine that binds to TNFRSF1A/TNFR1 and TNFRSF1B/TNFBR. It is mainly secreted by macrophages and can induce cell death of certain tumor cell lines. It is potent pyrogen causing fever by direct ac...
Gene Name
TNF
Uniprot ID
P01375
Uniprot Name
Tumor necrosis factor
Molecular Weight
25644.15 Da
Details2. Interleukin-1 beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein domain specific binding
Specific Function
Potent proinflammatory cytokine. Initially discovered as the major endogenous pyrogen, induces prostaglandin synthesis, neutrophil influx and activation, T-cell activation and cytokine production, ...
Gene Name
IL1B
Uniprot ID
P01584
Uniprot Name
Interleukin-1 beta
Molecular Weight
30747.7 Da
Details3. Interleukin-6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Interleukin-6 receptor binding
Specific Function
Cytokine with a wide variety of biological functions. It is a potent inducer of the acute phase response. Plays an essential role in the final differentiation of B-cells into Ig-secreting cells Inv...
Gene Name
IL6
Uniprot ID
P05231
Uniprot Name
Interleukin-6
Molecular Weight
23717.965 Da

Drug created at October 20, 2016 21:26 / Updated at February 21, 2021 18:53