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1-{[(3R)-3-methyl-4-({4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]phenyl}sulfonyl)piperazin-1-yl]methyl}cyclopropanecarboxamide

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Identification

Generic Name
1-{[(3R)-3-methyl-4-({4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]phenyl}sulfonyl)piperazin-1-yl]methyl}cyclopropanecarboxamide
DrugBank Accession Number
DB07624
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 449.488
Monoisotopic: 449.15961164
Chemical Formula
C19H26F3N3O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U11-beta-hydroxysteroid dehydrogenase 1Not AvailableHumans
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 benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / N-alkylpiperazines / Organosulfonamides / Cyclopropanecarboxylic acids and derivatives / Sulfonyls / Tertiary alcohols / Primary carboxylic acid amides / Fluorohydrins / Trialkylamines / Amino acids and derivatives
show 8 more
Substituents
1,4-diazinane / Alcohol / Alkyl fluoride / Alkyl halide / Amine / Amino acid or derivatives / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenesulfonamide
show 28 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
YJFULAYRAKPBCY-DYVFJYSZSA-N
InChI
InChI=1S/C19H26F3N3O4S/c1-13-11-24(12-18(7-8-18)16(23)26)9-10-25(13)30(28,29)15-5-3-14(4-6-15)17(2,27)19(20,21)22/h3-6,13,27H,7-12H2,1-2H3,(H2,23,26)/t13-,17+/m1/s1
IUPAC Name
1-{[(3R)-3-methyl-4-{4-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]benzenesulfonyl}piperazin-1-yl]methyl}cyclopropane-1-carboxamide
SMILES
[H][C@@]1(C)CN(CC2(CC2)C(N)=O)CCN1S(=O)(=O)C1=CC=C(C=C1)[C@](C)(O)C(F)(F)F

References

General References
Not Available
PubChem Compound
24856362
PubChem Substance
99444095
ChemSpider
23336276
BindingDB
50248569
ChEMBL
CHEMBL460962
ZINC
ZINC000039110046
PDBe Ligand
D4N
PDB Entries
3d4n

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
PropertyValueSource
Water Solubility0.194 mg/mLALOGPS
logP0.94ALOGPS
logP1.36Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.63Chemaxon
pKa (Strongest Basic)7.15Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area103.94 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity104.93 m3·mol-1Chemaxon
Polarizability42.75 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier-0.6186
Caco-2 permeable-0.6831
P-glycoprotein substrateSubstrate0.8045
P-glycoprotein inhibitor INon-inhibitor0.5129
P-glycoprotein inhibitor IINon-inhibitor0.5251
Renal organic cation transporterNon-inhibitor0.7587
CYP450 2C9 substrateNon-substrate0.7638
CYP450 2D6 substrateNon-substrate0.7966
CYP450 3A4 substrateSubstrate0.5089
CYP450 1A2 substrateNon-inhibitor0.871
CYP450 2C9 inhibitorNon-inhibitor0.8056
CYP450 2D6 inhibitorNon-inhibitor0.7891
CYP450 2C19 inhibitorNon-inhibitor0.8024
CYP450 3A4 inhibitorInhibitor0.7507
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.95
Ames testNon AMES toxic0.6291
CarcinogenicityNon-carcinogens0.7431
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4903 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9809
hERG inhibition (predictor II)Inhibitor0.6164
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0000900000-ec97120f94a91dd04b7e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002r-0009800000-77a8cc8c31965ef8fbbe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000m-3005900000-243308dcce322fd5852a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfr-0000900000-0ca5d088714d3dabee52
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ht9-0734900000-432ea6c19d231f6a03e1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k9t-0036900000-38b80fc2b1e8f7daf7ae
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.41469
predicted
DeepCCS 1.0 (2019)
[M+H]+195.81024
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.72276
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 11-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
  1. 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 21:24 / Updated at June 12, 2020 16:52