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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
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 Weight 808.0 g/mol
Molecular Formula C45H54FN7O6
XLogP35.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count11
Rotatable Bond Count11
Exact Mass g/mol
Monoisotopic Mass g/mol
Topological Polar Surface Area156
Heavy Atom Count59
Formal Charge0
Complexity1550
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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