2-(2-CHLORO-4-FLUOROPHENOXY)-2-METHYL-N-[(1R,2S,3S,5S,7S)-5-(METHYLSULFONYL)-2-ADAMANTYL]PROPANAMIDE
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Overview
- DrugBank ID
- DB08277
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- 2-(2-CHLORO-4-FLUOROPHENOXY)-2-METHYL-N-[(1R,2S,3S,5S,7S)-5-(METHYLSULFONYL)-2-ADAMANTYL]PROPANAMIDE
- DrugBank Accession Number
- DB08277
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 443.96
Monoisotopic: 443.133334959 - Chemical Formula
- C21H27ClFNO4S
- 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 phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Fluorobenzenes / Chlorobenzenes / Alkyl aryl ethers / Aryl fluorides / Aryl chlorides / Sulfones / Secondary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds show 5 more
- Substituents
- Alkyl aryl ether / Aromatic homopolycyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Chlorobenzene / Ether show 19 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- ULLPKOZNMAWTIP-JGSHYQHOSA-N
- InChI
- InChI=1S/C21H27ClFNO4S/c1-20(2,28-17-5-4-15(23)8-16(17)22)19(25)24-18-13-6-12-7-14(18)11-21(9-12,10-13)29(3,26)27/h4-5,8,12-14,18H,6-7,9-11H2,1-3H3,(H,24,25)/t12-,13-,14+,18-,21-
- IUPAC Name
- 2-(2-chloro-4-fluorophenoxy)-2-methyl-N-[(1R,2s,3S,5s,7s)-5-methanesulfonyladamantan-2-yl]propanamide
- SMILES
- [H][C@@]12C[C@@]3([H])C[C@@](C1)(C[C@@]([H])(C2)[C@@]3([H])NC(=O)C(C)(C)OC1=C(Cl)C=C(F)C=C1)S(C)(=O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 16040257
- PubChem Substance
- 99444748
- ChemSpider
- 26328287
- ZINC
- ZINC000100036563
- PDBe Ligand
- NN1
- PDB Entries
- 2ilt
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 0.00144 mg/mL ALOGPS logP 3.61 ALOGPS logP 2.99 Chemaxon logS -5.5 ALOGPS pKa (Strongest Acidic) 14.2 Chemaxon pKa (Strongest Basic) -4.6 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 72.47 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 108.71 m3·mol-1 Chemaxon Polarizability 44.42 Å3 Chemaxon Number of Rings 4 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 + 0.9966 Blood Brain Barrier + 0.7693 Caco-2 permeable - 0.5571 P-glycoprotein substrate Non-substrate 0.6768 P-glycoprotein inhibitor I Non-inhibitor 0.5726 P-glycoprotein inhibitor II Non-inhibitor 0.8888 Renal organic cation transporter Non-inhibitor 0.9137 CYP450 2C9 substrate Non-substrate 0.6285 CYP450 2D6 substrate Non-substrate 0.7953 CYP450 3A4 substrate Substrate 0.6967 CYP450 1A2 substrate Non-inhibitor 0.5349 CYP450 2C9 inhibitor Non-inhibitor 0.5243 CYP450 2D6 inhibitor Non-inhibitor 0.8883 CYP450 2C19 inhibitor Inhibitor 0.5785 CYP450 3A4 inhibitor Inhibitor 0.6711 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.747 Ames test Non AMES toxic 0.6142 Carcinogenicity Non-carcinogens 0.6371 Biodegradation Not ready biodegradable 0.9935 Rat acute toxicity 2.5462 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9955 hERG inhibition (predictor II) Non-inhibitor 0.6281
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03xr-3409000000-5f26ace219bd3bf6112c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0011900000-273987d2e607c142fc04 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0500900000-40f058e3ad64f6e58c54 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kb-0951100000-dfcaabd64a4ba99b6583 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000x-9431300000-ddb5723c9f183a6af99e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001m-2910000000-dbf1c8631985723f9a34 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000f-4922000000-cc65430c0b026e2843ea 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]- 195.35141 predictedDeepCCS 1.0 (2019) [M+H]+ 197.18272 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.78862 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 21:30 / Updated at June 12, 2020 16:52