Avadomide free base

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MedKoo CAT#: 205830

CAS#: 1015474-32-4 (free base)

Description: Avadomide, also known as CC-122, is an orally available pleiotropic pathway modulator with potential antineoplastic activity. CC-122 mimics an interferon response and has antitumor activity in DLBCL CC-122 binds Cereblon (CRBN) and promotes degradation of Aiolos and Ikaros in diffuse large B-cell lymphoma (DLBCL) and T cells in vitro, in vivo, and in patients, resulting in both cell autonomous as well as immunostimulatory effects.

Chemical Structure

Avadomide free base
CAS# 1015474-32-4 (free base)

Theoretical Analysis

MedKoo Cat#: 205830
Name: Avadomide free base
CAS#: 1015474-32-4 (free base)
Chemical Formula: C14H14N4O3
Exact Mass: 286.1066
Molecular Weight: 286.291
Elemental Analysis: C, 58.74; H, 4.93; N, 19.57; O, 16.77

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5.0g USD 5650.0 2 Weeks
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Related CAS #: 1398053-45-6 (HCl)   1015474-32-4 (free base)    

Synonym: CC 122; CC-122; CC122, Avadomide

IUPAC/Chemical Name: 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione


InChi Code: 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)

SMILES Code: O=C(C(N1C(C)=NC2=C(C(N)=CC=C2)C1=O)CC3)NC3=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 286.291 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hagner PR, Man HW, Fontanillo C, Wang M, Couto S, Breider M, Bjorklund C, Havens CG, Lu G, Rychak E, Raymon H, Narla RK, Barnes L, Khambatta G, Chiu H, Kosek J, Kang J, Amantangelo MD, Waldman M, Lopez-Girona A, Cai T, Pourdehnad M, Trotter M, Daniel TO, Schafer PH, Klippel A, Thakurta A, Chopra R, Gandhi AK. CC-122, a pleiotropic pathway modifier, mimics an interferon response and has antitumor activity in DLBCL. Blood. 2015 Aug 6;126(6):779-89. doi: 10.1182/blood-2015-02-628669. Epub 2015 May 22. PubMed PMID: 26002965; PubMed Central PMCID: PMC4528065.

2: Li Y, Carayannopoulos LN, Thomas M, Palmisano M, Zhou S. Exposure-response analysis to assess the concentration-QTc relationship of CC-122. Clin Pharmacol. 2016 Sep 9;8:117-25. doi: 10.2147/CPAA.S111867. eCollection 2016. PubMed PMID: 27672344; PubMed Central PMCID: PMC5024774.

3: Krönke J, Fink EC, Hollenbach PW, MacBeth KJ, Hurst SN, Udeshi ND, Chamberlain PP, Mani DR, Man HW, Gandhi AK, Svinkina T, Schneider RK, McConkey M, Järås M, Griffiths E, Wetzler M, Bullinger L, Cathers BE, Carr SA, Chopra R, Ebert BL. Lenalidomide induces ubiquitination and degradation of CK1α in del(5q) MDS. Nature. 2015 Jul 9;523(7559):183-188. doi: 10.1038/nature14610. Epub 2015 Jul 1. PubMed PMID: 26131937; PubMed Central PMCID: PMC4853910.

4: Cubillos-Zapata C, Cordoba R, Avendaño-Ortiz J, Arribas-Jiménez C, Hernández-Jiménez E, Toledano V, Villaescusa T, Moreno V, López-Collazo E. CC-122 immunomodulatory effects in refractory patients with diffuse large B-cell lymphoma. Oncoimmunology. 2016 Sep 16;5(12):e1231290. doi: 10.1080/2162402X.2016.1231290. eCollection 2016. PubMed PMID: 28255524; PubMed Central PMCID: PMC5325046.

5: Jacques V, Czarnik AW, Judge TM, Van der Ploeg LH, DeWitt SH. Differentiation of antiinflammatory and antitumorigenic properties of stabilized enantiomers of thalidomide analogs. Proc Natl Acad Sci U S A. 2015 Mar 24;112(12):E1471-9. doi: 10.1073/pnas.1417832112. Epub 2015 Mar 9. Erratum in: Proc Natl Acad Sci U S A. 2015 May 12;112(19):E2553. PubMed PMID: 25775521; PubMed Central PMCID: PMC4378388.

6: Nowakowski GS. Evolution: IMiDs to PPMs, revolution in DLBCL? Blood. 2015 Aug 6;126(6):698-700. doi: 10.1182/blood-2015-06-649483. PubMed PMID: 26251224.

7: Ito T, Handa H. Recent topics in IMiDs and cereblon. Rinsho Ketsueki. 2017;58(10):2067-2073. doi: 10.11406/rinketsu.58.2067. PubMed PMID: 28978850.

8: Camicia R, Winkler HC, Hassa PO. Novel drug targets for personalized precision medicine in relapsed/refractory diffuse large B-cell lymphoma: a comprehensive review. Mol Cancer. 2015 Dec 11;14:207. doi: 10.1186/s12943-015-0474-2. Review. PubMed PMID: 26654227; PubMed Central PMCID: PMC4676894.

9: Cubillos-Zapata C, Córdoba R, Avendaño-Ortiz J, Lopez-Collazo E. Thalidomide analog CC-122 induces a refractory state in monocytes from patients with diffuse large B cell lymphoma. Leuk Lymphoma. 2017 Aug;58(8):1999-2001. doi: 10.1080/10428194.2016.1272686. Epub 2017 Jan 16. Retraction in: Leuk Lymphoma. 2017 Aug;58(8):I. PubMed PMID: 28093007.

Additional Information

 In DLBCL cell lines, CC-122-induced degradation or short hairpin RNA-mediated knockdown of Aiolos and Ikaros correlates with increased transcription of interferon (IFN)-stimulated genes independent of IFN-α, -β, and -γ production and/or secretion and results in apoptosis in both activated B-cell (ABC) and germinal center B-cell DLBCL