Luxdegalutamide

Synopsis, Chemistry

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Also known as: Arv-766, 2750830-09-0, Arv766, 4-(4-((1-(4-((trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl)carbamoyl)phenyl)piperidin-4-yl)methyl)piperazin-1-yl)-n-((s)-2,6-dioxopiperidin-3-yl)-2-fluorobenzamide, Luxdegalutamide [inn], 5bd7r933pv

Molecular Formula

C₄₅H₅₄FN₇O₆

Molecular Weight

808.0 g/mol

InChI Key

RDPPBRKNBBXPNZ-PJXMSJPKSA-N

FDA UNII

5BD7R933PV

Luxdegalutamide is an orally bioavailable androgen receptor (AR)-targeted protein degrader, composed of an AR ligand attached to an E3 ligase recognition moiety and utilizing the proteolysis targeting chimera (PROTAC) technology, with potential antineoplastic activity. Upon oral administration, luxdegalutamide targets and binds to the AR ligand binding domain on the AR. E3 ligase is then recruited to the AR by the E3 ligase recognition moiety of luxdegalutamide and the AR is tagged by ubiquitin. This causes ubiquitination and degradation of AR by the proteasome, and prevents the expression of AR target genes and halts AR-mediated signaling. This inhibits the proliferation of AR-overexpressing tumor cells. In addition, the degradation of the AR releases luxdegalutamide, allowing it to bind to additional AR. AR plays a key role in the proliferation of castration-resistant prostate cancer cells (CRPC). Luxdegalutamide may degrade resistance-driving point mutations of AR, including the L702H mutation associated with treatments including abiraterone.

1 2D Structure

Luxdegalutamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[4-[[1-[4-[[3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]carbamoyl]phenyl]piperidin-4-yl]methyl]piperazin-1-yl]-N-[(3S)-2,6-dioxopiperidin-3-yl]-2-fluorobenzamide

2.1.2 InChI

InChI=1S/C45H54FN7O6/c1-44(2)42(45(3,4)43(44)59-33-12-8-30(26-47)37(25-33)58-5)50-39(55)29-6-9-31(10-7-29)52-18-16-28(17-19-52)27-51-20-22-53(23-21-51)32-11-13-34(35(46)24-32)40(56)48-36-14-15-38(54)49-41(36)57/h6-13,24-25,28,36,42-43H,14-23,27H2,1-5H3,(H,48,56)(H,50,55)(H,49,54,57)/t36-,42?,43?/m0/s1

2.1.3 InChI Key

RDPPBRKNBBXPNZ-PJXMSJPKSA-N

2.1.4 Canonical SMILES

CC1(C(C(C1OC2=CC(=C(C=C2)C#N)OC)(C)C)NC(=O)C3=CC=C(C=C3)N4CCC(CC4)CN5CCN(CC5)C6=CC(=C(C=C6)C(=O)NC7CCC(=O)NC7=O)F)C

2.1.5 Isomeric SMILES

CC1(C(C(C1OC2=CC(=C(C=C2)C#N)OC)(C)C)NC(=O)C3=CC=C(C=C3)N4CCC(CC4)CN5CCN(CC5)C6=CC(=C(C=C6)C(=O)N[C@H]7CCC(=O)NC7=O)F)C

2.2 Other Identifiers

2.2.1 UNII

5BD7R933PV

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Arv-766

2. 2750830-09-0

3. Arv766

4. 4-(4-((1-(4-((trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl)carbamoyl)phenyl)piperidin-4-yl)methyl)piperazin-1-yl)-n-((s)-2,6-dioxopiperidin-3-yl)-2-fluorobenzamide

5. Luxdegalutamide [inn]

6. 5bd7r933pv

7. Schembl23536786

8. Schembl23594097

9. Gtpl12624

10. Ex-a7714

11. Nsc847604

12. At41584

13. Nsc-847604

14. Ts-09678

15. Hy-153342

16. Cs-0693933

17. 4-[4-[[1-[4-[[[trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]a Mino]carbonyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-n-[(3s)-2,6-dioxo-3-piperidinyl]-2-fluoro-benzamide

18. 4-[4-[[1-[4-[[[trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-n-[(3s)-2,6-dioxo-3-piperidinyl]-2-fluorobenzamide

19. Benzamide, 4-[4-[[1-[4-[[[trans-3-(4-cyano-3-methoxyphenoxy)-2,2,4,4-tetramethylcyclobutyl]amino]carbonyl]phenyl]-4-piperidinyl]methyl]-1-piperazinyl]-n-[(3s)-2,6-dioxo-3-piperidinyl]-2-fluoro-

2.4 Create Date

2021-08-21

3 Chemical and Physical Properties

Molecular Formula	C₄₅H₅₄FN₇O₆
Molecular Weight	808.0 g/mol
XLogP3	5.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	11
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	156
Heavy Atom Count	59
Formal Charge	0
Complexity	1550
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1