(5S)-2-{[(1S)-1-(2-fluorophenyl)ethyl]amino}-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4(5H)-one
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Identification
- Generic Name
- (5S)-2-{[(1S)-1-(2-fluorophenyl)ethyl]amino}-5-methyl-5-(trifluoromethyl)-1,3-thiazol-4(5H)-one
- DrugBank Accession Number
- DB07310
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 320.306
Monoisotopic: 320.060646526 - Chemical Formula
- C13H12F4N2OS
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U11-beta-hydroxysteroid dehydrogenase 1 Not Available 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
- 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
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Fluorobenzenes
- Alternative Parents
- Aryl fluorides / Thiazolines / N-acylimines / Isothioureas / Propargyl-type 1,3-dipolar organic compounds / Carboxylic acids and derivatives / Carboximidamides / Azacyclic compounds / Organopnictogen compounds / Organofluorides show 4 more
- Substituents
- Alkyl fluoride / Alkyl halide / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Carbonyl group / Carboximidamide / Carboxylic acid derivative / Fluorobenzene show 15 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- KNHNFKZUNFPPQE-MADCSZMMSA-N
- InChI
- InChI=1S/C13H12F4N2OS/c1-7(8-5-3-4-6-9(8)14)18-11-19-10(20)12(2,21-11)13(15,16)17/h3-7H,1-2H3,(H,18,19,20)/t7-,12-/m0/s1
- IUPAC Name
- (5S)-2-{[(1S)-1-(2-fluorophenyl)ethyl]amino}-5-methyl-5-(trifluoromethyl)-4,5-dihydro-1,3-thiazol-4-one
- SMILES
- C[C@H](NC1=NC(=O)[C@](C)(S1)C(F)(F)F)C1=C(F)C=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 16105493
- PubChem Substance
- 99443781
- ChemSpider
- 16788070
- BindingDB
- 13754
- ChEMBL
- CHEMBL218006
- ZINC
- ZINC000014953779
- PDBe Ligand
- A21
- PDB Entries
- 3bzu
Clinical Trials
- Clinical Trials
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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 0.0131 mg/mL ALOGPS logP 3.31 ALOGPS logP 3.5 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 18.43 Chemaxon pKa (Strongest Basic) -0.52 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.46 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 71.45 m3·mol-1 Chemaxon Polarizability 26.67 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9092 Blood Brain Barrier + 0.9383 Caco-2 permeable - 0.5116 P-glycoprotein substrate Non-substrate 0.7245 P-glycoprotein inhibitor I Non-inhibitor 0.7637 P-glycoprotein inhibitor II Non-inhibitor 0.9547 Renal organic cation transporter Non-inhibitor 0.8453 CYP450 2C9 substrate Non-substrate 0.7232 CYP450 2D6 substrate Non-substrate 0.8387 CYP450 3A4 substrate Non-substrate 0.5445 CYP450 1A2 substrate Inhibitor 0.6384 CYP450 2C9 inhibitor Inhibitor 0.5 CYP450 2D6 inhibitor Non-inhibitor 0.9062 CYP450 2C19 inhibitor Inhibitor 0.7196 CYP450 3A4 inhibitor Non-inhibitor 0.7074 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6366 Ames test Non AMES toxic 0.6765 Carcinogenicity Non-carcinogens 0.8352 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.8408 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9951 hERG inhibition (predictor II) Non-inhibitor 0.8376
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0kmi-4913000000-d07d816c2681e7bd82d0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0009000000-d60155bcea2f5f2dd0e9 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0923000000-85d2d860d3e61c49197e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0209000000-ba31e2902be28ebc5981 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000b-2900000000-1984565a31a9cfa3361d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fai-0940000000-b5f906ffeb3e664f6624 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01xd-9880000000-2ab2456b3161853ccd1f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 168.53368 predictedDeepCCS 1.0 (2019) [M+H]+ 170.89168 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.44754 predictedDeepCCS 1.0 (2019)
Targets
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1. Details11-beta-hydroxysteroid dehydrogenase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Controls the reversible conversion of biologically active glucocorticoids such as cortisone to cortisol, and 11-dehydrocorticosterone to corticosterone in the presence of NADP(H) (PubMed:10497248, PubMed:12460758, PubMed:14973125, PubMed:15152005, PubMed:15280030, PubMed:17593962, PubMed:21453287, PubMed:27927697, PubMed:30902677). Participates in the corticosteroid receptor-mediated anti-inflammatory response, as well as metabolic and homeostatic processes (PubMed:10497248, PubMed:12414862, PubMed:15152005, PubMed:21453287). Plays a role in the secretion of aqueous humor in the eye, maintaining a normotensive, intraocular environment (PubMed:11481269). Bidirectional in vitro, predominantly functions as a reductase in vivo, thereby increasing the concentration of active glucocorticoids (PubMed:10497248, PubMed:11481269, PubMed:12414862, PubMed:12460758). It has broad substrate specificity, besides glucocorticoids, it accepts other steroid and sterol substrates (PubMed:15095019, PubMed:15152005, PubMed:17593962, PubMed:21453287). Interconverts 7-oxo- and 7-hydroxy-neurosteroids such as 7-oxopregnenolone and 7beta-hydroxypregnenolone, 7-oxodehydroepiandrosterone (3beta-hydroxy-5-androstene-7,17-dione) and 7beta-hydroxydehydroepiandrosterone (3beta,7beta-dihydroxyandrost-5-en-17-one), among others (PubMed:17593962). Catalyzes the stereo-specific conversion of the major dietary oxysterol, 7-ketocholesterol (7-oxocholesterol), into the more polar 7-beta-hydroxycholesterol metabolite (PubMed:15095019, PubMed:15152005). 7-oxocholesterol is one of the most important oxysterols, it participates in several events such as induction of apoptosis, accumulation in atherosclerotic lesions, lipid peroxidation, and induction of foam cell formation (PubMed:15095019). Mediates the 7-oxo reduction of 7-oxolithocholate mainly to chenodeoxycholate, and to a lesser extent to ursodeoxycholate, both in its free form and when conjugated to glycine or taurine, providing a link between glucocorticoid activation and bile acid metabolism (PubMed:21453287). Catalyzes the synthesis of 7-beta-25-dihydroxycholesterol from 7-oxo-25-hydroxycholesterol in vitro, which acts as a ligand for the G-protein-coupled receptor (GPCR) Epstein-Barr virus-induced gene 2 (EBI2) and may thereby regulate immune cell migration (PubMed:30902677)
- Specific Function
- 11-beta-hydroxysteroid dehydrogenase (NADP+) activity
- Gene Name
- HSD11B1
- Uniprot ID
- P28845
- Uniprot Name
- 11-beta-hydroxysteroid dehydrogenase 1
- Molecular Weight
- 32400.665 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:20 / Updated at June 12, 2020 16:52