Details of the Drug

General Information of Drug (ID: DMXI8CD)

Drug Name
TRC-253
Synonyms OUEHJEYKNYQVRC-UHFFFAOYSA-N; TRC253; SCHEMBL19128768; EX-A1808; 2110426-27-0; 5-(8-oxo-5-(6-(piperidin-4-yloxy)pyridin-3-yl)-6-thioxo-5,7-diazaspiro[3.4]octan-7-yl)-3-(trifluoromethyl)picolinonitrile
Indication
Disease Entry ICD 11 Status REF
Prostate cancer 2C82.0 Phase 1/2 [1]
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 502.5
Topological Polar Surface Area (xlogp) 3
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 10
Chemical Identifiers
Formula
C23H21F3N6O2S
IUPAC Name
5-[8-oxo-5-(6-piperidin-4-yloxypyridin-3-yl)-6-sulfanylidene-5,7-diazaspiro[3.4]octan-7-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile
Canonical SMILES
C1CC2(C1)C(=O)N(C(=S)N2C3=CN=C(C=C3)OC4CCNCC4)C5=CC(=C(N=C5)C#N)C(F)(F)F
InChI
InChI=1S/C23H21F3N6O2S/c24-23(25,26)17-10-15(13-29-18(17)11-27)31-20(33)22(6-1-7-22)32(21(31)35)14-2-3-19(30-12-14)34-16-4-8-28-9-5-16/h2-3,10,12-13,16,28H,1,4-9H2
InChIKey
OUEHJEYKNYQVRC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
130229812
TTD ID
D0SD9Z

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Androgen receptor messenger RNA (AR mRNA) TTKPW01 ANDR_HUMAN Antagonist [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 02 Neoplasm
Disease Class ICD-11: 2C82 Prostate cancer
The Studied Tissue Prostate
The Studied Disease Prostate cancer [ICD-11:2C82]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Androgen receptor messenger RNA (AR mRNA) DTT AR 4.81E-01 -0.23 -0.29
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT02987829) Phase 1/2A Study of TRC253, an Androgen Receptor Antagonist, in Metastatic Castration-resistant Prostate Cancer Patients. U.S. National Institutes of Health.
2 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
3 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. (Target id: 628).
4 Synthesis and biological activity of a novel, highly potent progesterone receptor antagonist. J Med Chem. 2000 Dec 28;43(26):5010-6.
5 Clinical pipeline report, company report or official report of ISIS Pharmaceuticals.
6 2011 Pipeline of Santaris Pharma.
7 Effect of essential oils, such as raspberry ketone and its derivatives, on antiandrogenic activity based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2111-4.
8 Rational design and synthesis of 4-((1R,2R)-2-hydroxycyclohexyl)-2(trifluoromethyl)benzonitrile (PF-998425), a novel, nonsteroidal androgen recepto... J Med Chem. 2008 Nov 13;51(21):7010-4.
9 Effect of flavonoids on androgen and glucocorticoid receptors based on in vitro reporter gene assay. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4706-10.
10 Antiinflammatory glucocorticoid receptor ligand with reduced side effects exhibits an altered protein-protein interaction profile. Proc Natl Acad Sci U S A. 2007 Dec 4;104(49):19244-9.