avadomide

{{Short description|Chemical compound}}

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| legal_status = Investigational

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| CAS_number = 1015474-32-4

| UNII = 28DZS29F59

| PubChem = 24967599

| DrugBank = DB14857

| ChEMBL = 3989934

| ChemSpiderID = 35521266

| IUPHAR_ligand = 10522

| KEGG = D11132

| IUPAC_name = 3-(5-Amino-2-methyl-4-oxoquinazolin-3-yl)piperidine-2,6-dione

| StdInChI=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)

| StdInChIKey = RSNPAKAFCAAMBH-UHFFFAOYSA-N

| SMILES = CC1=NC2=CC=CC(=C2C(=O)N1C3CCC(=O)NC3=O)N

| C = 14 | H = 14 | N = 4 | O = 3

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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.{{cite journal |last1=Nishi |first1=Hidemi |last2=Gotoh |first2=Kunihito |last3=Tomimaru |first3=Yoshito |last4=Kobayashi |first4=Shogo |last5=Sasaki |first5=Kazuki |last6=Iwagami |first6=Yoshifumi |last7=Yamada |first7=Daisaku |last8=Akita |first8=Hirofumi |last9=Asaoka |first9=Tadafumi |last10=Noda |first10=Takehiro |last11=Takahashi |first11=Hidenori |last12=Tanemura |first12=Masahiro |last13=Doki |first13=Yuichiro |last14=Eguchi |first14=Hidetoshi |title=Anti-tumor effect of avadomide in gemcitabine-resistant pancreatic ductal adenocarcinoma |journal=Cancer Chemotherapy and Pharmacology |date=October 2023 |volume=92 |issue=4 |pages=303–314 |doi=10.1007/s00280-023-04531-w|pmid=37491611 |pmc=10435408 }}{{cite journal |last1=Nastoupil |first1=Loretta J. |last2=Kuruvilla |first2=John |last3=Chavez |first3=Julio C. |last4=Bijou |first4=Fontanet |last5=Witzig |first5=Thomas E. |last6=Santoro |first6=Armando |last7=Flinn |first7=Ian W. |last8=Boccomini |first8=Carola |last9=Kenkre |first9=Vaishalee P. |last10=Corradini |first10=Paolo |last11=Isufi |first11=Iris |last12=Andorsky |first12=David J. |last13=Klein |first13=Leonard M. |last14=Greenwald |first14=Daniel R. |last15=Sangha |first15=Randeep |last16=Shen |first16=Frank |last17=Hagner |first17=Patrick |last18=Li |first18=Yan |last19=Dobmeyer |first19=Juergen |last20=Gong |first20=Nian |last21=Uttamsingh |first21=Shailaja |last22=Pourdehnad |first22=Michael |last23=Ribrag |first23=Vincent |title=Phase Ib study of avadomide (CC-122) in combination with rituximab in patients with relapsed/refractory diffuse large B-cell lymphoma and follicular lymphoma |journal=EJHaem |date=May 2022 |volume=3 |issue=2 |pages=394–405 |doi=10.1002/jha2.394|pmid=35846031 |pmc=9175947 }}{{cite journal |last1=Heim |first1=Christopher |last2=Hartmann |first2=Marcus D. |title=High-resolution structures of the bound effectors avadomide (CC-122) and iberdomide (CC-220) highlight advantages and limitations of the MsCI4 soaking system |journal=Acta Crystallographica Section D Structural Biology |date=1 March 2022 |volume=78 |issue=3 |pages=290–298 |doi=10.1107/S2059798322000092|pmid=35234143 |pmc=8900816 |bibcode=2022AcCrD..78..290H }}{{cite journal |last1=Hagner |first1=Patrick R. |last2=Chiu |first2=Hsiling |last3=Chopra |first3=Vivek S. |last4=Colombo |first4=Martino |last5=Patel |first5=Nisha |last6=Estevez |first6=Maria Ortiz |last7=Waldman |first7=Michelle F. |last8=Loos |first8=Remco |last9=Towfic |first9=Fadi |last10=Gandhi |first10=Anita K. |title=Interactome of Aiolos/Ikaros Reveals Combination Rationale of Cereblon Modulators with HDAC Inhibitors in DLBCL |journal=Clinical Cancer Research |date=2 August 2022 |volume=28 |issue=15 |pages=3367–3377 |doi=10.1158/1078-0432.CCR-21-3347|pmid=35583604 |pmc=9662945 }}{{cite journal |last1=Ribrag |first1=Vincent |last2=Chavez |first2=Julio C. |last3=Boccomini |first3=Carola |last4=Kaplan |first4=Jason |last5=Chandler |first5=Jason C. |last6=Santoro |first6=Armando |last7=Corradini |first7=Paolo |last8=Flinn |first8=Ian W. |last9=Advani |first9=Ranjana |last10=Cassier |first10=Philippe A. |last11=Sangha |first11=Randeep |last12=Kenkre |first12=Vaishalee P. |last13=Isufi |first13=Iris |last14=Uttamsingh |first14=Shailaja |last15=Hagner |first15=Patrick R. |last16=Gandhi |first16=Anita K. |last17=Shen |first17=Frank |last18=Michelliza |first18=Sophie |last19=Haeske |first19=Harald |last20=Hege |first20=Kristen |last21=Pourdehnad |first21=Michael |last22=Kuruvilla |first22=John |title=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 |journal=EJHaem |date=February 2022 |volume=3 |issue=1 |pages=139–153 |doi=10.1002/jha2.375|pmid=35846221 |pmc=9176062 }} The deuterated S-enantiomer, SP-3164 (DRX-164) is in development at Salarius Pharmaceuticals.{{cite journal |last1=Jacques |first1=Vincent |last2=Czarnik |first2=Anthony W |last3=Judge |first3=Thomas M |last4=Van der Ploeg |first4=Lex HT |last5=DeWitt |first5=Sheila |date=2015 |title=Differentiation of antiinflammatory and antitumorigenic properties of stabilized enantiomers of thalidomide analogs |journal=Proc Natl Acad Sci U S A |volume=112 |issue=12 |page=E1471 |doi=10.1073/pnas.1417832112 |pmid=25775521|pmc=4378388 }}{{cite journal |last1=Santiesteban |first1=Daniela Y |last2=Duncan |first2=Aundrietta D |last3=Mirza |first3=Nadeem Q |last4=Jacques |first4=Vincent |last5=DeWitt |first5=Sheila |last6=Iyer |first6=Swami P. |title=SP-3164, a Novel Cereblon-Binding Protein Degrader, Shows Activity in Preclinical Lymphoma Models |journal=Blood |date=15 November 2022 |volume=140 |issue=Supplement 1 |pages=8865–8866 |doi=10.1182/blood-2022-167495|s2cid=254268049 |doi-access=free}}