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Also known as: Arv-110, 2222112-77-6, Bavdegalutamide [inn], Bavdegalutamide [usan], Arv110, H6nym0v650

Molecular Formula

C₄₁H₄₃ClFN₉O₆

Molecular Weight

812.3 g/mol

InChI Key

CLCTZVRHDOAUGJ-UHFFFAOYSA-N

FDA UNII

H6NYM0V650

Bavdegalutamide is an orally available selective androgen receptor (AR)-targeted protein degrader, using the proteolysis targeting chimera (PROTAC) technology, with potential antineoplastic activity. Bavdegalutamide is composed of an AR ligand attached to an E3 ligase recognition moiety. Upon oral administration, bavdegalutamide targets and binds to the AR ligand binding domain. E3 ligase is recruited to the AR by the E3 ligase recognition moiety and the AR target protein is tagged by ubiquitin. This causes ubiquitination and degradation of AR by the proteasome. This prevents the expression of AR target genes and halts AR-mediated signaling. This results in an inhibition of proliferation in AR-overexpressing tumor cells. In addition, the degradation of the AR protein releases the ARV-110 is released and can bind to additional AR target proteins. AR plays a key role in the proliferation of castration-resistant prostate cancer cells (CRPC).

1 2D Structure

Bavdegalutamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-[4-(3-chloro-4-cyanophenoxy)cyclohexyl]-6-[4-[[4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl]piperazin-1-yl]methyl]piperidin-1-yl]pyridazine-3-carboxamide

2.1.2 InChI

InChI=1S/C41H43ClFN9O6/c42-31-19-28(4-1-25(31)22-44)58-27-5-2-26(3-6-27)45-38(54)33-7-9-36(48-47-33)51-13-11-24(12-14-51)23-49-15-17-50(18-16-49)35-21-30-29(20-32(35)43)40(56)52(41(30)57)34-8-10-37(53)46-39(34)55/h1,4,7,9,19-21,24,26-27,34H,2-3,5-6,8,10-18,23H2,(H,45,54)(H,46,53,55)

2.1.3 InChI Key

CLCTZVRHDOAUGJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CC(CCC1NC(=O)C2=NN=C(C=C2)N3CCC(CC3)CN4CCN(CC4)C5=C(C=C6C(=C5)C(=O)N(C6=O)C7CCC(=O)NC7=O)F)OC8=CC(=C(C=C8)C#N)Cl

2.2 Other Identifiers

2.2.1 UNII

H6NYM0V650

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Arv-110

2. 2222112-77-6

3. Bavdegalutamide [inn]

4. Bavdegalutamide [usan]

5. Arv110

6. H6nym0v650

7. 3-pyridazinecarboxamide, N-[trans-4-(3-chloro-4-cyanophenoxy)cyclohexyl]-6-[4-[[4-[2-(2,6-dioxo-3-piperidinyl)-6-fluoro-2,3-dihydro-1,3-dioxo-1h-isoindol-5-yl]-1-piperazinyl]methyl]-1-piperidinyl]-

8. N-(trans-4-(3-chloro-4-cyanophenoxy)cyclohexyl)-6-(4-((4-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperazin-1-yl)methyl)piperidin-1-yl)pyridazine-3-carboxamide

9. 3-pyridazinecarboxamide, N-(trans-4-(3-chloro-4-cyanophenoxy)cyclohexyl)-6-(4-((4-(2-(2,6-dioxo-3-piperidinyl)-6-fluoro-2,3-dihydro-1,3-dioxo-1h-isoindol-5-yl)-1-piperazinyl)methyl)-1-piperidinyl)-

10. N-((1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl)-6-(4-((4-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxo-2,3-dihydro-1h-isoindol-5-yl)piperazin-1-yl)methyl)piperidin-1-yl)pyridazine-3-carboxamide

11. Starbld0008416

12. Unii-h6nym0v650

13. Arv-110 (protac)

14. Arv-110 [who-dd]

15. Chembl4862963

16. Schembl20046698

17. Gtpl11512

18. Ex-a5017

19. S6965

20. Who 11542

21. At25206

22. Ac-37002

23. As-84821

24. Compound 406 [wo2018071606a1]

25. Hy-138641

26. Cs-0159884

27. 6-[4-({4-[2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxo-2,3-dihydro-1h-isoindol-5-yl]piperazin-1-yl}methyl)piperidin-1-yl]-n-[(1r,4r)-4-(3-chloro-4-cyanophenoxy)cyclohexyl]pyridazine-3-carboxamide

2.4 Create Date

2018-06-23

3 Chemical and Physical Properties

Molecular Formula	C₄₁H₄₃ClFN₉O₆
Molecular Weight	812.3 g/mol
XLogP3	3.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	9
Exact Mass	811.3008860 g/mol
Monoisotopic Mass	811.3008860 g/mol
Topological Polar Surface Area	181 Å²
Heavy Atom Count	58
Formal Charge	0
Complexity	1590
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1