Mezigdomide

Mezigdomide
Legal status
Legal status	Investigational;
Identifiers
	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;
CAS Number	2259648-80-9;
PubChem CID	137379043;
ChemSpider	84451594;
UNII	LA88IH4O02;
ChEMBL	ChEMBL4648616;
Chemical and physical data
Formula	C32H30FN5O4
Molar mass	567.621 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	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; Key:YTINZZFBHWSAGL-NDEPHWFRSA-N;

Mezigdomide is a cereblon E3 ligase modulator developed by Bristol Myers Squibb to treat multiple myeloma.^[1]^[2]^[3]^[4]^[5]

References

^ Richardson, Paul G.; Trudel, Suzanne; Quach, Hang; Popat, Rakesh; Lonial, Sagar; Orlowski, Robert Z.; Kim, Kihyun; Mateos, María-Victoria; Pawlyn, Charlotte; Ramasamy, Karthik; Martinez-Lopez, Joaquín; Spirli, Alessia; Casas-Avilés, Ignacio; Gong, Jing; Amatangelo, Michael; Katz, Jessica; Maciag, Paulo; Peluso, Teresa; Bahlis, Nizar J. (15 November 2022). "Mezigdomide (CC-92480), a Potent, Novel Cereblon E3 Ligase Modulator (CELMoD), Combined with Dexamethasone (DEX) in Patients (pts) with Relapsed/Refractory Multiple Myeloma (RRMM): Preliminary Results from the Dose-Expansion Phase of the CC-92480-MM-001 Trial". Blood. 140 (Supplement 1): 1366–1368. doi:10.1182/blood-2022-157945.
^ Gaffney, Bonny; Shi, Yu; de Jong, Petrus; Sanchez, Manuel; Fontanillo, Celia; Lopez-Girona, Antonia; Boss, Isaac W.; Kurtova, Antonina; Carrancio, Soraya; Wong, Lilly; Pierce, Daniel W. (15 November 2022). "Mezigdomide (CC-92480), a Novel Cereblon E3 Ligase Modulator, Induces Vulnerability of Multiple Myeloma Cells to T-Cell-Mediated Killing". Blood. 140 (Supplement 1): 7108–7109. doi:10.1182/blood-2022-157939.
^ Richardson, Paul G.; Trudel, Suzanne; Popat, Rakesh; Mateos, María-Victoria; Vangsted, Annette J.; Ramasamy, Karthik; Martinez-Lopez, Joaquín; Quach, Hang; Orlowski, Robert Z.; Arnao, Mario; Lonial, Sagar; Karanes, Chatchada; Pawlyn, Charlotte; Kim, Kihyun; Oriol, Albert; Berdeja, Jesus G.; Rodríguez Otero, Paula; Casas-Avilés, Ignacio; Spirli, Alessia; Poon, Jennifer; Li, Shaoyi; Gong, Jing; Wong, Lilly; Lamba, Manisha; Pierce, Daniel W.; Amatangelo, Michael; Peluso, Teresa; Maciag, Paulo; Katz, Jessica; Pourdehnad, Michael; Bahlis, Nizar J. (14 September 2023). "Mezigdomide plus Dexamethasone in Relapsed and Refractory Multiple Myeloma". New England Journal of Medicine. 389 (11): 1009–1022. doi:10.1056/NEJMoa2303194. PMID 37646702. S2CID 261336795.
^ Midha, Shonali; Hartley-Brown, Monique A.; Mo, Clifton C.; Hossain, Shahrier; Nadeem, Omar; O’Donnell, Elizabeth K.; Bianchi, Giada; Sperling, Adam S.; Laubach, Jacob P.; Richardson, Paul G. (2 November 2023). "A safety review of recently approved and emerging drugs for patients with relapsed or refractory multiple myeloma". Expert Opinion on Drug Safety. 22 (11): 1049–1071. doi:10.1080/14740338.2023.2274420. PMID 37906232. S2CID 264672983.
^ Richardson, Paul G; Mateos, María-Victoria; Vangsted, Annette J; Ramasamy, Karthik; Abildgaard, Niels; Ho, P Joy; Quach, Hang; Bahlis, Nizar J (3 June 2022). "The role of E3 ubiquitin ligase in multiple myeloma: potential for cereblon E3 ligase modulators in the treatment of relapsed/refractory disease". Expert Review of Proteomics. 19 (4–6): 235–246. doi:10.1080/14789450.2022.2142564. PMID 36342226. S2CID 253382728.

[1] Richardson, Paul G.; Trudel, Suzanne; Quach, Hang; Popat, Rakesh; Lonial, Sagar; Orlowski, Robert Z.; Kim, Kihyun; Mateos, María-Victoria; Pawlyn, Charlotte; Ramasamy, Karthik; Martinez-Lopez, Joaquín; Spirli, Alessia; Casas-Avilés, Ignacio; Gong, Jing; Amatangelo, Michael; Katz, Jessica; Maciag, Paulo; Peluso, Teresa; Bahlis, Nizar J. (15 November 2022). "Mezigdomide (CC-92480), a Potent, Novel Cereblon E3 Ligase Modulator (CELMoD), Combined with Dexamethasone (DEX) in Patients (pts) with Relapsed/Refractory Multiple Myeloma (RRMM): Preliminary Results from the Dose-Expansion Phase of the CC-92480-MM-001 Trial". Blood. 140 (Supplement 1): 1366–1368. doi:10.1182/blood-2022-157945.

[2] Gaffney, Bonny; Shi, Yu; de Jong, Petrus; Sanchez, Manuel; Fontanillo, Celia; Lopez-Girona, Antonia; Boss, Isaac W.; Kurtova, Antonina; Carrancio, Soraya; Wong, Lilly; Pierce, Daniel W. (15 November 2022). "Mezigdomide (CC-92480), a Novel Cereblon E3 Ligase Modulator, Induces Vulnerability of Multiple Myeloma Cells to T-Cell-Mediated Killing". Blood. 140 (Supplement 1): 7108–7109. doi:10.1182/blood-2022-157939.

[3] Richardson, Paul G.; Trudel, Suzanne; Popat, Rakesh; Mateos, María-Victoria; Vangsted, Annette J.; Ramasamy, Karthik; Martinez-Lopez, Joaquín; Quach, Hang; Orlowski, Robert Z.; Arnao, Mario; Lonial, Sagar; Karanes, Chatchada; Pawlyn, Charlotte; Kim, Kihyun; Oriol, Albert; Berdeja, Jesus G.; Rodríguez Otero, Paula; Casas-Avilés, Ignacio; Spirli, Alessia; Poon, Jennifer; Li, Shaoyi; Gong, Jing; Wong, Lilly; Lamba, Manisha; Pierce, Daniel W.; Amatangelo, Michael; Peluso, Teresa; Maciag, Paulo; Katz, Jessica; Pourdehnad, Michael; Bahlis, Nizar J. (14 September 2023). "Mezigdomide plus Dexamethasone in Relapsed and Refractory Multiple Myeloma". New England Journal of Medicine. 389 (11): 1009–1022. doi:10.1056/NEJMoa2303194. PMID 37646702. S2CID 261336795.

[4] Midha, Shonali; Hartley-Brown, Monique A.; Mo, Clifton C.; Hossain, Shahrier; Nadeem, Omar; O’Donnell, Elizabeth K.; Bianchi, Giada; Sperling, Adam S.; Laubach, Jacob P.; Richardson, Paul G. (2 November 2023). "A safety review of recently approved and emerging drugs for patients with relapsed or refractory multiple myeloma". Expert Opinion on Drug Safety. 22 (11): 1049–1071. doi:10.1080/14740338.2023.2274420. PMID 37906232. S2CID 264672983.

[5] Richardson, Paul G; Mateos, María-Victoria; Vangsted, Annette J; Ramasamy, Karthik; Abildgaard, Niels; Ho, P Joy; Quach, Hang; Bahlis, Nizar J (3 June 2022). "The role of E3 ubiquitin ligase in multiple myeloma: potential for cereblon E3 ligase modulators in the treatment of relapsed/refractory disease". Expert Review of Proteomics. 19 (4–6): 235–246. doi:10.1080/14789450.2022.2142564. PMID 36342226. S2CID 253382728.

[1]

[2]

[3]

[4]

[5]

Legal status

Legal status	Investigational
Identifiers
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
CAS Number	2259648-80-9
PubChem CID	137379043
ChemSpider	84451594
UNII	LA88IH4O02
ChEMBL	ChEMBL4648616
Chemical and physical data
Formula	C₃₂H₃₀FN₅O₄
Molar mass	567.621 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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 Key:YTINZZFBHWSAGL-NDEPHWFRSA-N