(R)-Bicalutamide

Identification

Generic Name
(R)-Bicalutamide
DrugBank Accession Number
DB02932
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 430.373
Monoisotopic: 430.061040456
Chemical Formula
C18H14F4N2O4S
Synonyms
  • (-)-Bicalutamide

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 / Benzenesulfonyl compounds / Benzonitriles / N-arylamides / Fluorobenzenes / Aryl fluorides / Tertiary alcohols / Sulfones / Secondary carboxylic acid amides / Nitriles
show 6 more
Substituents
Alcohol / Alkyl fluoride / Alkyl halide / Anilide / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Benzenesulfonyl group / Benzonitrile / Carbonitrile
show 22 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
sulfone, monocarboxylic acid amide, nitrile, monofluorobenzenes, (trifluoromethyl)benzenes (CHEBI:3090)
Affected organisms
Not Available

Chemical Identifiers

UNII
Z9DL98I0AF
CAS number
113299-40-4
InChI Key
LKJPYSCBVHEWIU-KRWDZBQOSA-N
InChI
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)/t17-/m0/s1
IUPAC Name
(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
SMILES
C[C@](O)(CS(=O)(=O)C1=CC=C(F)C=C1)C(=O)NC1=CC(=C(C=C1)C#N)C(F)(F)F

References

General References
Not Available
PubChem Compound
56069
PubChem Substance
46506892
ChemSpider
50614
BindingDB
18678
ChEBI
39589
ChEMBL
CHEMBL63560
ZINC
ZINC000000538564
PDBe Ligand
198
Wikipedia
Bicalutamide
PDB Entries
1z95 / 4fia / 4la0 / 4ojb / 4ok1 / 4okb / 4okt / 4okw / 4okx / 4olm

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 Solubility0.00928 mg/mLALOGPS
logP2.7ALOGPS
logP2.71Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.78Chemaxon
pKa (Strongest Basic)-4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area107.26 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity96.59 m3·mol-1Chemaxon
Polarizability37.05 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9471
Blood Brain Barrier+0.859
Caco-2 permeable-0.6085
P-glycoprotein substrateNon-substrate0.6741
P-glycoprotein inhibitor INon-inhibitor0.7171
P-glycoprotein inhibitor IINon-inhibitor0.9178
Renal organic cation transporterNon-inhibitor0.9572
CYP450 2C9 substrateNon-substrate0.6883
CYP450 2D6 substrateNon-substrate0.8087
CYP450 3A4 substrateNon-substrate0.5536
CYP450 1A2 substrateNon-inhibitor0.8513
CYP450 2C9 inhibitorNon-inhibitor0.6246
CYP450 2D6 inhibitorNon-inhibitor0.8683
CYP450 2C19 inhibitorInhibitor0.7976
CYP450 3A4 inhibitorInhibitor0.7879
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5662
Ames testNon AMES toxic0.7134
CarcinogenicityNon-carcinogens0.6067
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4383 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9959
hERG inhibition (predictor II)Non-inhibitor0.8759
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-MSsplash10-052o-9550100000-db5a9cf33efd5830315b
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014r-0790400000-444f61324c94f14a8bd7
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014r-0790400000-444f61324c94f14a8bd7
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014r-0790400000-444f61324c94f14a8bd7
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014r-0790400000-444f61324c94f14a8bd7
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00kr-0960100000-4968dc10ab5126b250fd
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0a4r-0900000000-be3d61ea6718b1a266f7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-973cad78855e47c269d8
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090100000-20f788a0c47f74a34677
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0190000000-3250849f86d81e5a1ccc
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0920000000-c6287e7ed8af3e61b68d
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-288e128fcd4d86f55c7b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-dfa9042147701f410cfc
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-1900000000-7a1c430c2255a7b39987
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090100000-4929146a4ac14d2c0de9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0190000000-1bcff4596e442981afcb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0920000000-324077c607be45cabdd3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-a3c7bc0a67e22e87302f
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-0aa23f85f03e382e4714
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-000i-0900000000-ab7066f32e0b9943a354
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0a4i-0090000000-61c01e04e122c122b457
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kr-0950000000-fedf6b90d4a3883451f3
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-015i-0980500000-97c1afd3bc16b90c3045
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014r-0980000000-3a338b0f3949554d007a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abi-0900000000-2d68f75d889d6c64172f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-61b081ebf1d21de93299
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-5e5c2556d842f3aa760f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-886b545ad9f30e2200f7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-015i-0980500000-8571297a3004da7cdb92
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014r-0980000000-113a5d57e5a1bd008dc7
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0abi-0900000000-40b0e258813875d2bb62
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-518a42868fd01d31e192
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-d35728316b745781478b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0900000000-6bee736a7085e637306c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014r-0960000000-1dcd39dc2124e74b8385
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014r-0790400000-444f61324c94f14a8bd7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014r-0970000000-2fc9526294afe2f7526a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0aor-0900000000-8fc6a2f1d151d10bc79e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0130900000-2f7d7db6c8a88f8a3b72
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kr-0960100000-4968dc10ab5126b250fd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0900000000-be3d61ea6718b1a266f7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0020900000-0fefcfc6187d07a83bee
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0030900000-b45794de57578a79ce2e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zgi-0190400000-8c800f3f4b66fce5447b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-1420900000-aef5b7c464cb28db3378
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1931000000-1e6feb7f27053f0a75d8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0595-5940000000-96d585d1e1f243306ccd
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]-185.78569
predicted
DeepCCS 1.0 (2019)
[M+H]+188.18126
predicted
DeepCCS 1.0 (2019)
[M+Na]+194.09378
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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52