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Proxalutamide

Proxalutamide

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Also known as: 1398046-21-3, Pruxelutamide, Gt-0918, Proxalutamide [who-dd], Qx6o64gp40, 4-(4,4-dimethyl-3-(6-(3-(2-oxazolyl)propyl)-3-pyridinyl)-5-oxo-2-thioxo-1-imidazolidinyl)-3-fluoro-2-(trifluoromethyl)-benzonitrile

Molecular Formula

C₂₄H₁₉F₄N₅O₂S

Molecular Weight

517.5 g/mol

InChI Key

KCBJGVDOSBKVKP-UHFFFAOYSA-N

FDA UNII

QX6O64GP40

Proxalutamide is an orally bioavailable androgen receptor (AR) antagonist with potential antineoplastic activity. Upon oral administration, proxalutamide binds to AR in target tissues, inhibits androgen-induced receptor activation, and facilitates the formation of inactive complexes that cannot translocate to the nucleus. This prevents binding to and transcription of AR-responsive genes that regulate prostate cancer cell proliferation. In addition, proxalutamide induces AR downregulation, thereby further preventing AR-mediated signaling. This ultimately leads to an inhibition of growth in AR-expressing prostate cancer cells. AR is overexpressed in prostate cancer and plays a key role in prostate cancer cell proliferation.

1 2D Structure

Proxalutamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[4,4-dimethyl-3-[6-[3-(1,3-oxazol-2-yl)propyl]pyridin-3-yl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-3-fluoro-2-(trifluoromethyl)benzonitrile

2.1.2 InChI

InChI=1S/C24H19F4N5O2S/c1-23(2)21(34)32(17-9-6-14(12-29)19(20(17)25)24(26,27)28)22(36)33(23)16-8-7-15(31-13-16)4-3-5-18-30-10-11-35-18/h6-11,13H,3-5H2,1-2H3

2.1.3 InChI Key

KCBJGVDOSBKVKP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1(C(=O)N(C(=S)N1C2=CN=C(C=C2)CCCC3=NC=CO3)C4=C(C(=C(C=C4)C#N)C(F)(F)F)F)C

2.2 Other Identifiers

2.2.1 UNII

QX6O64GP40

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(4,4-dimethyl-3-(6-(3-(2-oxazolyl)propyl)-3-pyridinyl)-5-oxo-2-thioxo-1-imidazolidinyl)-3-fluoro-2-(trifluoromethyl)benzonitrile

2. Gt 0918

3. Gt-0918

4. Gt0918

2.3.2 Depositor-Supplied Synonyms

1. 1398046-21-3

2. Pruxelutamide

3. Gt-0918

4. Proxalutamide [who-dd]

5. Qx6o64gp40

6. 4-(4,4-dimethyl-3-(6-(3-(2-oxazolyl)propyl)-3-pyridinyl)-5-oxo-2-thioxo-1-imidazolidinyl)-3-fluoro-2-(trifluoromethyl)-benzonitrile

7. 4-[4,4-dimethyl-3-[6-[3-(1,3-oxazol-2-yl)propyl]pyridin-3-yl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-3-fluoro-2-(trifluoromethyl)benzonitrile

8. 4-(4,4-dimethyl-3-(6-(3-(oxazol-2-yl)propyl)pyridin-3-yl)-5-oxo-2-thioxoimidazolidin-1-yl)-3-fluoro-2-(trifluoromethyl)benzonitrile

9. Unii-qx6o64gp40

10. Pruxelutamide [inn]

11. Chembl4594417

12. Schembl12494226

13. Gtpl11992

14. Dtxsid901102678

15. Ex-a5434

16. Gt0918

17. At29744

18. Sb17303

19. Hy-103184

20. Cs-0025229

21. Q27287540

22. 4-(4,4-dimethyl-3-(6-(3-(oxazol-2-yl)propyl)pyridin-3-yl)-5-oxo-2-thioxoimidazolidin-1-yl)-3-fluoro-2-(trifluoromethyl) Benzonitrile

2.4 Create Date

2012-10-01

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₁₉F₄N₅O₂S
Molecular Weight	517.5 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	6
Exact Mass	517.11955869 g/mol
Monoisotopic Mass	517.11955869 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	894
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

4 Pharmacology and Biochemistry

4.1 Mechanism of Action

Proxalutamide is an antagonist at the androgen receptor which leads to inhibition of androgen-induced receptor activation and results in formation of inactive complexes that are not able to translocate to the nucleus. It also induces androgen receptor downregulation, furthering adrogen-induced receptor activation. This drug is being investigated for its potential antineoplastic activity and is being investigated specifically against prostate cancer and COVID-19.