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Also known as: Trc253, 2110426-27-0, Gng9gq9y27, Trc-253 [who-dd], Trc-253, Jnj-63576253 (free base)

Molecular Formula

C₂₃H₂₁F₃N₆O₂S

Molecular Weight

502.5 g/mol

InChI Key

OUEHJEYKNYQVRC-UHFFFAOYSA-N

FDA UNII

GNG9GQ9Y27

Androgen Receptor Antagonist TRC253 is an orally bioavailable androgen receptor (AR) antagonist, with potential antineoplastic activity. Upon oral administration, AR antagonist TRC253 specifically binds to both wild-type and certain mutant forms of AR, thereby preventing androgen-induced receptor activation and facilitating the formation of inactive complexes that cannot translocate to the nucleus. This prevents binding to and transcription of AR-responsive genes, inhibits the expression of genes that regulate prostate cancer cell proliferation, and may lead to an inhibition of growth of tumor cells in which AR is overexpressed and/or mutated. AR is often overexpressed and/or mutated in prostate cancers and plays a key role in proliferation, survival and chemoresistance of tumor cells.

1 2D Structure

TRC253

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

OUEHJEYKNYQVRC-UHFFFAOYSA-N

2.1.4 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

2.2 Other Identifiers

2.2.1 UNII

GNG9GQ9Y27

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Trc253

2. 2110426-27-0

3. Gng9gq9y27

4. Trc-253 [who-dd]

5. Trc-253

6. Jnj-63576253 (free Base)

7. Jnj63576253 Hcl

8. 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

9. Unii-gng9gq9y27

10. Chembl4858811

11. Schembl19128768

12. Bdbm493530

13. Ex-a1808

14. Nsc831271

15. Akos037652172

16. Nsc-831271

17. Us10981926, Cpd No. 43

18. Ac-36765

19. Hy-115282

20. Cs-0034880

21. 5-[5-oxo-8-[6-(4-piperidyloxy)- 3-pyridyl]-7-thioxo-6,8- Diazaspiro[3.4]octan-6-yl]-3- (trifluoromethyl)pyridine-2- Carbonitrile

2.4 Create Date

2017-10-07

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₁F₃N₆O₂S
Molecular Weight	502.5 g/mol
XLogP3	3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	4
Exact Mass	502.13987959 g/mol
Monoisotopic Mass	502.13987959 g/mol
Topological Polar Surface Area	127 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	884
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1