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1 Drugs in Development

1 Drugs in Development

Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Cc-92480, 2259648-80-9, Unii-la88ih4o02, Mezigdomide [usan], La88ih4o02, Cc92480

Molecular Formula

C₃₂H₃₀FN₅O₄

Molecular Weight

567.6 g/mol

InChI Key

YTINZZFBHWSAGL-NDEPHWFRSA-N

FDA UNII

LA88IH4O02

Mezigdomide is a modulator of the E3 ubiquitin ligase complex containing cereblon (CRL4-CRBN E3 ubiquitin ligase), with potential immunomodulating and antineoplastic activities. Upon administration, mezigdomide specifically binds to cereblon (CRBN), thereby affecting the ubiquitin E3 ligase activity, and targeting certain substrate proteins for ubiquitination. This induces proteasome-mediated degradation of certain transcription factors, some of which are transcriptional repressors in T-cells. This leads to modulation of the immune system, including activation of T-lymphocytes, and downregulation of the activity of other proteins, some of which play key roles in the proliferation of certain cancer cell types. CRBN, the substrate recognition component of the CRL4-CRBN E3 ubiquitin ligase complex, plays a key role in the ubiquitination of certain proteins.

1 2D Structure

Mezigdomide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[4-[[4-[[2-[(3S)-2,6-dioxopiperidin-3-yl]-1-oxo-3H-isoindol-4-yl]oxymethyl]phenyl]methyl]piperazin-1-yl]-3-fluorobenzonitrile

2.1.2 InChI

InChI=1S/C32H30FN5O4/c33-26-16-23(17-34)8-9-27(26)37-14-12-36(13-15-37)18-21-4-6-22(7-5-21)20-42-29-3-1-2-24-25(29)19-38(32(24)41)28-10-11-30(39)35-31(28)40/h1-9,16,28H,10-15,18-20H2,(H,35,39,40)/t28-/m0/s1

2.1.3 InChI Key

YTINZZFBHWSAGL-NDEPHWFRSA-N

2.1.4 Canonical SMILES

C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3OCC4=CC=C(C=C4)CN5CCN(CC5)C6=C(C=C(C=C6)C#N)F

2.1.5 Isomeric SMILES

C1CC(=O)NC(=O)[C@H]1N2CC3=C(C2=O)C=CC=C3OCC4=CC=C(C=C4)CN5CCN(CC5)C6=C(C=C(C=C6)C#N)F

2.2 Other Identifiers

2.2.1 UNII

LA88IH4O02

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Cc-92480

2. 2259648-80-9

3. Unii-la88ih4o02

4. Mezigdomide [usan]

5. La88ih4o02

6. Cc92480

7. Who 11455

8. (s)-4-(4-(4-(((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)oxy)methyl)benzyl)piperazin-1-yl)-3-fluorobenzonitrile

9. 4-[4-[[4-[[2-[(3s)-2,6-dioxopiperidin-3-yl]-1-oxo-3h-isoindol-4-yl]oxymethyl]phenyl]methyl]piperazin-1-yl]-3-fluorobenzonitrile

10. (83s)-12-fluoro-71,82,86-trioxo-71,73-dihydro-6-oxa-7(4,2)-isoindola-2(1,4)-piperazina-8(3)-piperidina-1(1),4(1,4)-dibenzenaoctaphane-14-carbonitrile

11. Benzonitrile, 4-(4-((4-(((2-((3s)-2,6-dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1hisoindol-4-yl)oxy)methyl)phenyl)methyl)-1-piperazinyl)-3-fluoro-

12. Qfc

13. Mezigdomide [who-dd]

14. Mezigdomide [inn]

15. Chembl4648616

16. Schembl20608563

17. Gtpl12718

18. Bcp32805

19. Ex-a5597

20. S8975

21. Akos040732735

22. At18067

23. Compound 4 [pmid: 32130004]

24. Ms-30267

25. Hy-129395

26. Cc 92480; Cc92480

27. Cs-0105182

28. 4-(4-((4-(((2-((3s)-2,6-dioxopiperidin-3-yl)-1-oxo-2,3-dihydro-1h-isoindol-4- Yl)oxy)methyl)phenyl)methyl)piperazin-1-yl)-3-fluorobenzonitrile

29. 4-[4-({4-[({2-[(3s)-2,6-dioxopiperidin-3-yl]-1-oxo-2,3-dihydro-1h-isoindol-4-yl}oxy)methyl]phenyl}methyl)piperazin-1-yl]-3-fluorobenzonitrile

30. Benzonitrile, 4-(4-((4-(((2-((3s)-2,6-dioxo-3-piperidinyl)-2,3-dihydro-1-oxo-1h-isoindol-4-yl)oxy)methyl)phenyl)methyl)-1-piperazinyl)-3-fluoro-

2.4 Create Date

2019-03-16

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₃₀FN₅O₄
Molecular Weight	567.6 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	106
Heavy Atom Count	42
Formal Charge	0
Complexity	1050
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

4 Drug and Medication Information

4.1 Drug Indication

Treatment of mature B-cell neoplasms

Drugs in Development

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