Avadomide

Last updated
Avadomide
Avadomide.svg
Legal status
Legal status
  • Investigational
Identifiers
  • 3-(5-Amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C14H14N4O3
Molar mass 286.291 g·mol−1
3D model (JSmol)
  • Cc1nc2cccc(N)c2c(=O)n1C1CCC(=O)NC1=O
  • InChI=1S/C14H14N4O3/c1-7-16-9-4-2-3-8(15)12(9)14(21)18(7)10-5-6-11(19)17-13(10)20/h2-4,10H,5-6,15H2,1H3,(H,17,19,20)
  • Key:RSNPAKAFCAAMBH-UHFFFAOYSA-N

Avadomide (CC-122) is an experimental cereblon E3 ligase modulator, or thalidomide analog (molecular glue) that was discovered and studied by Celgene to see if it was effective against cancer. [1] [2] [3] [4] [5] The deuterated S-enantiomer, SP-3164 (DRX-164) is in development at Salarius Pharmaceuticals. [6] [7]

References

  1. ↑ Nishi, Hidemi; Gotoh, Kunihito; Tomimaru, Yoshito; Kobayashi, Shogo; Sasaki, Kazuki; Iwagami, Yoshifumi; Yamada, Daisaku; Akita, Hirofumi; Asaoka, Tadafumi; Noda, Takehiro; Takahashi, Hidenori; Tanemura, Masahiro; Doki, Yuichiro; Eguchi, Hidetoshi (October 2023). "Anti-tumor effect of avadomide in gemcitabine-resistant pancreatic ductal adenocarcinoma". Cancer Chemotherapy and Pharmacology. 92 (4): 303–314. doi:10.1007/s00280-023-04531-w. PMC   10435408 . PMID   37491611.
  2. ↑ Nastoupil, Loretta J.; Kuruvilla, John; Chavez, Julio C.; Bijou, Fontanet; Witzig, Thomas E.; Santoro, Armando; Flinn, Ian W.; Boccomini, Carola; Kenkre, Vaishalee P.; Corradini, Paolo; Isufi, Iris; Andorsky, David J.; Klein, Leonard M.; Greenwald, Daniel R.; Sangha, Randeep; Shen, Frank; Hagner, Patrick; Li, Yan; Dobmeyer, Juergen; Gong, Nian; Uttamsingh, Shailaja; Pourdehnad, Michael; Ribrag, Vincent (May 2022). "Phase Ib study of avadomide (CC-122) in combination with rituximab in patients with relapsed/refractory diffuse large B-cell lymphoma and follicular lymphoma". EJHaem. 3 (2): 394–405. doi:10.1002/jha2.394. PMC   9175947 . PMID   35846031.
  3. ↑ Heim, Christopher; Hartmann, Marcus D. (1 March 2022). "High-resolution structures of the bound effectors avadomide (CC-122) and iberdomide (CC-220) highlight advantages and limitations of the MsCI4 soaking system". Acta Crystallographica Section D Structural Biology. 78 (3): 290–298. Bibcode:2022AcCrD..78..290H. doi:10.1107/S2059798322000092. PMC   8900816 . PMID   35234143.
  4. ↑ Hagner, Patrick R.; Chiu, Hsiling; Chopra, Vivek S.; Colombo, Martino; Patel, Nisha; Estevez, Maria Ortiz; Waldman, Michelle F.; Loos, Remco; Towfic, Fadi; Gandhi, Anita K. (2 August 2022). "Interactome of Aiolos/Ikaros Reveals Combination Rationale of Cereblon Modulators with HDAC Inhibitors in DLBCL". Clinical Cancer Research. 28 (15): 3367–3377. doi:10.1158/1078-0432.CCR-21-3347. PMC   9662945 . PMID   35583604.
  5. ↑ Ribrag, Vincent; Chavez, Julio C.; Boccomini, Carola; Kaplan, Jason; Chandler, Jason C.; Santoro, Armando; Corradini, Paolo; Flinn, Ian W.; Advani, Ranjana; Cassier, Philippe A.; Sangha, Randeep; Kenkre, Vaishalee P.; Isufi, Iris; Uttamsingh, Shailaja; Hagner, Patrick R.; Gandhi, Anita K.; Shen, Frank; Michelliza, Sophie; Haeske, Harald; Hege, Kristen; Pourdehnad, Michael; Kuruvilla, John (February 2022). "Phase Ib study of combinations of avadomide (CC-122), CC-223, CC-292, and rituximab in patients with relapsed/refractory diffuse large B-cell lymphoma". EJHaem. 3 (1): 139–153. doi:10.1002/jha2.375. PMC   9176062 . PMID   35846221.
  6. ↑ Jacques, Vincent; Czarnik, Anthony W; Judge, Thomas M; Van der Ploeg, Lex HT; DeWitt, Sheila (2015). "Differentiation of antiinflammatory and antitumorigenic properties of stabilized enantiomers of thalidomide analogs". Proc Natl Acad Sci U S A. 112 (12): E1471. doi:10.1073/pnas.1417832112. PMC   4378388 . PMID   25775521.
  7. ↑ Santiesteban, Daniela Y; Duncan, Aundrietta D; Mirza, Nadeem Q; Jacques, Vincent; DeWitt, Sheila; Iyer, Swami P. (15 November 2022). "SP-3164, a Novel Cereblon-Binding Protein Degrader, Shows Activity in Preclinical Lymphoma Models". Blood. 140 (Supplement 1): 8865–8866. doi: 10.1182/blood-2022-167495 . S2CID   254268049.
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