Details of the Drug

General Information of Drug (ID: DMGIZF5)

Drug Name
Hydroxyflutamide
Synonyms
HFT; Hydroxyniphtholide; PC1193; Sch 16423; Hydroxy-flutamide; OH-flutamide; Sch-16423; Alpha, alpha, alpha-trifluoro-2-methyl-4'-nitro-m-lactotoluidide; Alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide; 2-Hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide; 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Indication
Disease Entry ICD 11 Status REF
Prostate cancer 2C82.0 Approved [1]
Therapeutic Class
Anticancer Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 292.21
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C11H11F3N2O4
IUPAC Name
2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Canonical SMILES
CC(C)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O
InChI
InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)
InChIKey
YPQLFJODEKMJEF-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
91649
CAS Number
52806-53-8
TTD ID
D0BC2E
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Androgen receptor (AR) TTS64P2 ANDR_HUMAN Antagonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1) OTQRET2B S5A1_HUMAN Gene/Protein Processing [3]
Androgen receptor (AR) OTUBKAZZ ANDR_HUMAN Drug Response [4]
Beta-microseminoprotein (MSMB) OTYORAJC MSMB_HUMAN Gene/Protein Processing [3]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Post-Translational Modifications [5]
Cadherin-2 (CDH2) OTH0Y56P CADH2_HUMAN Post-Translational Modifications [5]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Post-Translational Modifications [5]
Cholesterol side-chain cleavage enzyme, mitochondrial (CYP11A1) OT2NV3AN CP11A_HUMAN Gene/Protein Processing [3]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [5]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [5]
Plastin-2 (LCP1) OTK61F2A PLSL_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Prostate cancer
ICD Disease Classification 2C82.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Androgen receptor (AR) DTT AR 2.13E-01 -0.07 -0.11
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2862).
2 Drug insight: role of the androgen receptor in the development and progression of prostate cancer. Nat Clin Pract Oncol. 2007 Apr;4(4):236-44.
3 Androgen receptor modulation following combination exposure to brominated flame-retardants. Sci Rep. 2018 Mar 19;8(1):4843. doi: 10.1038/s41598-018-23181-0.
4 TBECH, 1,2-dibromo-4-(1,2 dibromoethyl) cyclohexane, alters androgen receptor regulation in response to mutations associated with prostate cancer. Toxicol Appl Pharmacol. 2016 Sep 15;307:91-101. doi: 10.1016/j.taap.2016.07.018. Epub 2016 Jul 27.
5 Anti-androgen 2-hydroxyflutamide modulates cadherin, catenin and androgen receptor phosphorylation in androgen-sensitive LNCaP and androgen-independent PC3 prostate cancer cell lines acting via PI3K/Akt and MAPK/ERK1/2 pathways. Toxicol In Vitro. 2017 Apr;40:324-335. doi: 10.1016/j.tiv.2017.01.019. Epub 2017 Feb 2.