GLPG-0974

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

Identification

Generic Name
GLPG-0974
DrugBank Accession Number
DB15406
Background

GLPG-0974 is under investigation in clinical trial NCT01721980 (Multiple Ascending Dose Study of GLPG0974 in Healthy Subjects).

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 485.0
Monoisotopic: 484.1223562
Chemical Formula
C25H25ClN2O4S
Synonyms
Not Available
External IDs
  • GLPG0974

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFree fatty acid receptor 2
antagonist
Humans
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
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
X7REK61AIS
CAS number
1391076-61-1
InChI Key
MPMKMQHJHDHPBE-RUZDIDTESA-N
InChI
InChI=1S/C25H25ClN2O4S/c1-25(11-13-28(25)23(31)20-16-33-21-9-3-2-8-19(20)21)24(32)27(12-5-10-22(29)30)15-17-6-4-7-18(26)14-17/h2-4,6-9,14,16H,5,10-13,15H2,1H3,(H,29,30)/t25-/m1/s1
IUPAC Name
4-{1-[(2R)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidin-2-yl]-N-[(3-chlorophenyl)methyl]formamido}butanoic acid
SMILES
C[C@@]1(CCN1C(=O)C1=CSC2=C1C=CC=C2)C(=O)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1

References

General References
Not Available
ChemSpider
35033253
BindingDB
50032334
ChEMBL
CHEMBL3353541
ZINC
ZINC000200856271

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentUlcerative Colitis1
1CompletedTreatmentHealthy Subjects (HS)2

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 Solubility0.001 mg/mLALOGPS
logP4.07ALOGPS
logP4.13Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)4.18Chemaxon
pKa (Strongest Basic)-1.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area77.92 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity128.28 m3·mol-1Chemaxon
Polarizability50.93 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-0170-0200900000-9e9974168804a2f9b5d9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bu9-2273900000-957f42b80aa86689eddc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03du-5942800000-9e0e720807079452d890
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-1364900000-c1c2b734e12afd15ade0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01r6-9821000000-381c06365c36fae5f231
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-8961000000-890bc76a9a66f01bf20b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
G protein-coupled receptor that is activated by a major product of dietary fiber digestion, the short chain fatty acids (SCFAs), and that plays a role in the regulation of whole-body energy homeostasis and in intestinal immunity. In omnivorous mammals, the short chain fatty acids acetate, propionate and butyrate are produced primarily by the gut microbiome that metabolizes dietary fibers. SCFAs serve as a source of energy but also act as signaling molecules. That G protein-coupled receptor is probably coupled to the pertussis toxin-sensitive, G(i/o)-alpha family of G proteins but also to the Gq family (PubMed:12496283, PubMed:12711604, PubMed:23589301). Its activation results in the formation of inositol 1,4,5-trisphosphate, the mobilization of intracellular calcium, the phosphorylation of the MAPK3/ERK1 and MAPK1/ERK2 kinases and the inhibition of intracellular cAMP accumulation. May play a role in glucose homeostasis by regulating the secretion of GLP-1, in response to short-chain fatty acids accumulating in the intestine. May also regulate the production of LEP/Leptin, a hormone acting on the central nervous system to inhibit food intake. Finally, may also regulate whole-body energy homeostasis through adipogenesis regulating both differentiation and lipid storage of adipocytes. In parallel to its role in energy homeostasis, may also mediate the activation of the inflammatory and immune responses by SCFA in the intestine, regulating the rapid production of chemokines and cytokines. May also play a role in the resolution of the inflammatory response and control chemotaxis in neutrophils. In addition to SCFAs, may also be activated by the extracellular lectin FCN1 in a process leading to activation of monocytes and inducing the secretion of interleukin-8/IL-8 in response to the presence of microbes (PubMed:21037097). Among SCFAs, the fatty acids containing less than 6 carbons, the most potent activators are probably acetate, propionate and butyrate (PubMed:12496283, PubMed:12711604). Exhibits a SCFA-independent constitutive G protein-coupled receptor activity (PubMed:23066016).
Specific Function
G protein-coupled receptor activity
Gene Name
FFAR2
Uniprot ID
O15552
Uniprot Name
Free fatty acid receptor 2
Molecular Weight
37143.375 Da
References
  1. Li M, van Esch BCAM, Henricks PAJ, Folkerts G, Garssen J: The Anti-inflammatory Effects of Short Chain Fatty Acids on Lipopolysaccharide- or Tumor Necrosis Factor alpha-Stimulated Endothelial Cells via Activation of GPR41/43 and Inhibition of HDACs. Front Pharmacol. 2018 May 23;9:533. doi: 10.3389/fphar.2018.00533. eCollection 2018. [Article]

Drug created at May 20, 2019 15:26 / Updated at June 30, 2022 20:48