Tarenflurbil
Identification
- Generic Name
- Tarenflurbil
- DrugBank Accession Number
- DB05289
- Background
Tarenflurbil is an investigational drug that was studied in patients with mild Alzheimer's disease. It is a selective amyloid lowering agent (SALA) that reduces levels of the toxic peptide amyloid beta 42 (Aβ42) in cultured human cells and in animal models. Aβ42 is the primary initiator of neurotoxicity and amyloid plaque development in the brains of Alzheimer's disease patients. In June 2008 development of the drug for Alzheimer's disease was discontinued. Tarenflurbil has also been used in trials studying the treatment of Prostate Cancer.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 244.2609
Monoisotopic: 244.089957865 - Chemical Formula
- C15H13FO2
- Synonyms
- (−)-(2R)-2-(2-fluorobiphenyl-4-yl)propanoic acid
- (2R)-2-(2-fluorobiphenyl-4-yl)propanoic acid
- (R)-2-fluoro-α-methyl(1,1'-biphenyl)-4-acetic acid
- (R)-flurbiprofen
- Tarenflurbil
- External IDs
- E-7869
- MPC-7869
Pharmacology
- Indication
Investigated for use/treatment in alzheimer's disease and prostate cancer.
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- Pharmacodynamics
Not Available
- Mechanism of action
MPC-7869 is not an inhibitor of cyclooxygenase enzymes (COX-1 and COX-2). The compound modulates the signal transduction and transcription activation pathways associated with nuclear factor kappaB (NFkappaB), a principle transcription factor in the expression of many molecules involved in cell growth, cell death and inflammation. In addition, MPC-7869 has recently been shown to modulate gamma-secretase and selectively lower levels of Abeta42 peptide in vitro and in vivo, and to reduce amyloid pathology in the brain. MPC-7869 has an excellent safety profile and is very potent in animal models of cancer and Alzheimer's disease. In transgenic mouse studies, MPC-7869 reduced brain amyloid levels and prevented memory loss.
Target Actions Organism UNF-kappa-B essential modulator Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Flurizan
Categories
- Drug Categories
- Acids, Acyclic
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Antirheumatic Agents
- Benzene Derivatives
- Biphenyl Compounds
- Central Nervous System Agents
- Cyclooxygenase Inhibitors
- Enzyme Inhibitors
- Gamma Secretase Inhibitors and Modulators
- Peripheral Nervous System Agents
- Propionates
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Biphenyls and derivatives
- Direct Parent
- Biphenyls and derivatives
- Alternative Parents
- Phenylpropanoic acids / Monocyclic monoterpenoids / Aromatic monoterpenoids / Fluorobenzenes / Aryl fluorides / Monocarboxylic acids and derivatives / Carboxylic acids / Organofluorides / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- 2-phenylpropanoic-acid / Aromatic homomonocyclic compound / Aromatic monoterpenoid / Aryl fluoride / Aryl halide / Biphenyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fluorobenzene show 11 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- flurbiprofen (CHEBI:38666)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 501W00OOWA
- CAS number
- 51543-40-9
- InChI Key
- SYTBZMRGLBWNTM-SNVBAGLBSA-N
- InChI
- InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)/t10-/m1/s1
- IUPAC Name
- (2R)-2-{2-fluoro-[1,1'-biphenyl]-4-yl}propanoic acid
- SMILES
- C[C@@H](C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 92337
- PubChem Substance
- 175426967
- ChemSpider
- 83361
- BindingDB
- 50172473
- ChEBI
- 38666
- ChEMBL
- CHEMBL190083
- ZINC
- ZINC000000008667
- PDBe Ligand
- FLR
- Wikipedia
- Tarenflurbil
- PDB Entries
- 3r94 / 3rr3 / 7euv
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Alzheimer's Disease (AD) / Dementia 1 3 Terminated Treatment Alzheimer's Disease (AD) 1 3 Terminated Treatment Alzheimer's Disease (AD) / Dementia 1 2 Unknown Status Treatment Prostate Cancer 1 1 Completed Not Available Healthy Volunteers (HV) 1
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
Property Value Source Water Solubility 0.0249 mg/mL ALOGPS logP 3.57 ALOGPS logP 3.94 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 4.42 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 67.29 m3·mol-1 Chemaxon Polarizability 25.31 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9824 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.76 P-glycoprotein inhibitor I Non-inhibitor 0.9061 P-glycoprotein inhibitor II Non-inhibitor 0.9739 Renal organic cation transporter Non-inhibitor 0.912 CYP450 2C9 substrate Non-substrate 0.7247 CYP450 2D6 substrate Non-substrate 0.9249 CYP450 3A4 substrate Non-substrate 0.7205 CYP450 1A2 substrate Inhibitor 0.8663 CYP450 2C9 inhibitor Inhibitor 0.8949 CYP450 2D6 inhibitor Non-inhibitor 0.9546 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9674 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8752 Ames test Non AMES toxic 0.9659 Carcinogenicity Non-carcinogens 0.5554 Biodegradation Not ready biodegradable 0.9861 Rat acute toxicity 3.1121 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9849 hERG inhibition (predictor II) Non-inhibitor 0.9116
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.19579 predictedDeepCCS 1.0 (2019) [M+H]+ 160.55397 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.9121 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Regulatory subunit of the IKK core complex which phosphorylates inhibitors of NF-kappa-B thus leading to the dissociation of the inhibitor/NF-kappa-B complex and ultimately the degradation of the i...
- Gene Name
- IKBKG
- Uniprot ID
- Q9Y6K9
- Uniprot Name
- NF-kappa-B essential modulator
- Molecular Weight
- 48197.35 Da
Drug created at November 18, 2007 18:23 / Updated at February 21, 2021 18:51