(R)-3-BROMO-2-HYDROXY-2-METHYL-N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]PROPANAMIDE

Identification

Generic Name
(R)-3-BROMO-2-HYDROXY-2-METHYL-N-[4-NITRO-3-(TRIFLUOROMETHYL)PHENYL]PROPANAMIDE
DrugBank Accession Number
DB07454
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 371.107
Monoisotopic: 369.97760408
Chemical Formula
C11H10BrF3N2O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAndrogen receptorNot 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 trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Trifluoromethylbenzenes
Direct Parent
Trifluoromethylbenzenes
Alternative Parents
Anilides / Nitrobenzenes / N-arylamides / Nitroaromatic compounds / Tertiary alcohols / Secondary carboxylic acid amides / Bromohydrins / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Organic oxides
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Substituents
Alcohol / Alkyl bromide / Alkyl fluoride / Alkyl halide / Allyl-type 1,3-dipolar organic compound / Anilide / Aromatic homomonocyclic compound / Bromohydrin / C-nitro compound / Carbonyl group
show 24 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QDSWNDMHSBZXKX-JTQLQIEISA-N
InChI
InChI=1S/C11H10BrF3N2O4/c1-10(19,5-12)9(18)16-6-2-3-8(17(20)21)7(4-6)11(13,14)15/h2-4,19H,5H2,1H3,(H,16,18)/t10-/m0/s1
IUPAC Name
(2R)-3-bromo-2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
SMILES
C[C@](O)(CBr)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

References

General References
Not Available
PubChem Compound
5287785
PubChem Substance
99443925
ChemSpider
4450086
BindingDB
18699
ChEMBL
CHEMBL296323
ZINC
ZINC000013581050
PDBe Ligand
BHM
PDB Entries
2ax9

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0041 mg/mLALOGPS
logP2.82ALOGPS
logP2.71Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)11.64Chemaxon
pKa (Strongest Basic)-4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area92.47 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity71.7 m3·mol-1Chemaxon
Polarizability27.07 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9872
Blood Brain Barrier+0.7983
Caco-2 permeable-0.5349
P-glycoprotein substrateNon-substrate0.5865
P-glycoprotein inhibitor INon-inhibitor0.7256
P-glycoprotein inhibitor IINon-inhibitor0.8918
Renal organic cation transporterNon-inhibitor0.9737
CYP450 2C9 substrateNon-substrate0.803
CYP450 2D6 substrateNon-substrate0.838
CYP450 3A4 substrateSubstrate0.5113
CYP450 1A2 substrateNon-inhibitor0.6433
CYP450 2C9 inhibitorNon-inhibitor0.6561
CYP450 2D6 inhibitorNon-inhibitor0.8727
CYP450 2C19 inhibitorInhibitor0.5904
CYP450 3A4 inhibitorNon-inhibitor0.7638
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6257
Ames testNon AMES toxic0.6312
CarcinogenicityNon-carcinogens0.6287
BiodegradationNot ready biodegradable0.9968
Rat acute toxicity2.6611 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9879
hERG inhibition (predictor II)Non-inhibitor0.8156
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a5i-3490000000-893cbf276429d2bf19d7
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]-156.18327
predicted
DeepCCS 1.0 (2019)
[M+H]+159.44334
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.93852
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 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 21:21 / Updated at June 12, 2020 16:52