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

Identification

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Name
1-{[(3R)-3-methyl-4-({4-[(1S)-2,2,2-trifluoro-1-hydroxy-1-methylethyl]phenyl}sulfonyl)piperazin-1-yl]methyl}cyclopropanecarboxamide
Accession Number
DB07624
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 449.488
Monoisotopic: 449.15961164
Chemical Formula
C19H26F3N3O4S
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCorticosteroid 11-beta-dehydrogenase isozyme 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
24856362
PubChem Substance
99444095
ChemSpider
23336276
BindingDB
50248569
ChEMBL
CHEMBL460962
HET
D4N
PDB Entries
3d4n

Clinical Trials

Clinical Trials
Not Available

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
Polarizability42.67 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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Benzenesulfonamide / Benzenesulfonyl group / N-alkylpiperazine / Cyclopropanecarboxylic acid or derivatives / 1,4-diazinane / Piperazine / Organosulfonic acid amide / Tertiary alcohol / Sulfonyl / Organosulfonic acid or derivatives
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 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. [PubMed:10592235]

Drug created on September 15, 2010 15:24 / Updated on August 02, 2019 08:10