(1S,3R,4S,5S,7S)-4-{[2-(4-METHOXYPHENOXY)-2-METHYLPROPANOYL]AMINO}ADAMANTANE-1-CARBOXAMIDE
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Identification
- Generic Name
- (1S,3R,4S,5S,7S)-4-{[2-(4-METHOXYPHENOXY)-2-METHYLPROPANOYL]AMINO}ADAMANTANE-1-CARBOXAMIDE
- DrugBank Accession Number
- DB08280
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 386.4846
Monoisotopic: 386.220557458 - Chemical Formula
- C22H30N2O4
- 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
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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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Anisoles
- Direct Parent
- Anisoles
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Alkyl aryl ethers / Secondary carboxylic acid amides / Primary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Alkyl aryl ether / Anisole / Aromatic homopolycyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Ether / Hydrocarbon derivative / Methoxybenzene / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- MNVKIDPRYUGTTG-YINOZDTMSA-N
- InChI
- InChI=1S/C22H30N2O4/c1-21(2,28-17-6-4-16(27-3)5-7-17)20(26)24-18-14-8-13-9-15(18)12-22(10-13,11-14)19(23)25/h4-7,13-15,18H,8-12H2,1-3H3,(H2,23,25)(H,24,26)/t13-,14-,15+,18-,22-
- IUPAC Name
- (1s,3R,4s,5S,7s)-4-[2-(4-methoxyphenoxy)-2-methylpropanamido]adamantane-1-carboxamide
- SMILES
- [H][C@@]12C[C@@]3([H])C[C@@](C1)(C[C@@]([H])(C2)[C@@]3([H])NC(=O)C(C)(C)OC1=CC=C(OC)C=C1)C(N)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 15942677
- PubChem Substance
- 99444751
- ChemSpider
- 26328288
- ZINC
- ZINC000100036578
- PDBe Ligand
- NN4
- PDB Entries
- 2irw
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 0.0117 mg/mL ALOGPS logP 2.84 ALOGPS logP 2.41 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 14.84 Chemaxon pKa (Strongest Basic) -0.44 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 90.65 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 104.46 m3·mol-1 Chemaxon Polarizability 42.33 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 Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9875 Blood Brain Barrier - 0.532 Caco-2 permeable - 0.6224 P-glycoprotein substrate Substrate 0.5264 P-glycoprotein inhibitor I Non-inhibitor 0.6845 P-glycoprotein inhibitor II Inhibitor 0.5569 Renal organic cation transporter Non-inhibitor 0.9406 CYP450 2C9 substrate Non-substrate 0.8427 CYP450 2D6 substrate Non-substrate 0.8001 CYP450 3A4 substrate Substrate 0.6545 CYP450 1A2 substrate Non-inhibitor 0.8352 CYP450 2C9 inhibitor Non-inhibitor 0.6939 CYP450 2D6 inhibitor Non-inhibitor 0.9424 CYP450 2C19 inhibitor Non-inhibitor 0.8079 CYP450 3A4 inhibitor Non-inhibitor 0.7223 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7394 Ames test Non AMES toxic 0.6802 Carcinogenicity Non-carcinogens 0.8633 Biodegradation Not ready biodegradable 0.9918 Rat acute toxicity 2.3978 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9983 hERG inhibition (predictor II) Non-inhibitor 0.8441
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00xu-2901000000-69aa5ea48de2d4dde9ea Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0019-0096000000-a6f292560c3f1dbdb9fe Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-6946000000-361f9126e413f075aefb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00or-3962000000-19cdbe2c4c2c8cfc5ad7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0il0-6928000000-ecc84ff35b724b696846 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004l-2903000000-284e752ebd8506ed1f34 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-5597000000-d39563bce0257e090747 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]- 181.48708 predictedDeepCCS 1.0 (2019) [M+H]+ 183.32402 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.92982 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