CC-90009 | CAS#1860875-51-9 | cereblon modulator

MedKoo Cat#: 207005 | Name: CC-90009

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

CC-90009 is a cereblon modulator. CC-90009 specifically binds to CRBN, thereby affecting the activity of the ubiquitin E3 ligase complex. This leads to the ubiquitination of certain substrate proteins and induces the proteasome-mediated degradation of certain transcription factors, including Ikaros (IKZF1) and Aiolos (IKZF3), which are transcriptional repressors in T-cells. This reduces the levels of these transcription factors, and modulates the activity of the immune system, which may include the activation of T-lymphocytes. .

Chemical Structure

CC-90009

CAS#1860875-51-9

Theoretical Analysis

MedKoo Cat#: 207005

Name: CC-90009

CAS#: 1860875-51-9

Chemical Formula: C22H18ClF2N3O4

Exact Mass: 461.0954

Molecular Weight: 461.85

Elemental Analysis: C, 57.21; H, 3.93; Cl, 7.68; F, 8.23; N, 9.10; O, 13.86

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,350.00	Ready to ship
500mg	USD 2,850.00	Ready to Ship
1g	USD 3,850.00	Ready to ship

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Related CAS #

No Data

Synonym

CC-90009; CC 90009; CC90009; Eragidomide

IUPAC/Chemical Name

2-(4-chlorophenyl)-N-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)-2,2-difluoroacetamide

InChi Key

PWBHUSLMHZLGRN-UHFFFAOYSA-N

InChi Code

InChI=1S/C22H18ClF2N3O4/c23-15-4-2-14(3-5-15)22(24,25)21(32)26-10-12-1-6-16-13(9-12)11-28(20(16)31)17-7-8-18(29)27-19(17)30/h1-6,9,17H,7-8,10-11H2,(H,26,32)(H,27,29,30)

SMILES Code

O=C(NCC1=CC2=C(C(N(C(CC3)C(NC3=O)=O)C2)=O)C=C1)C(F)(C4=CC=C(Cl)C=C4)F

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

Shelf Life

>3 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

More Info

A modulator of cereblon (CRBN), which is part of the cullin 4-RING E3 ubiquitin ligase complex (CRL4-CRBN E3 ubiquitin ligase; CUL4-CRBN E3 ubiquitin ligase), with potential immunomodulating and pro-apoptotic activities.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#S20S01C02

QC Data

View QC data: current batch, Lot#S20S01C02

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

CC-90009 is a cereblon modulator and binds to CRBN.

In vitro activity:

Biochemical, structural, and molecular characterization demonstrates that CC-90009 coopts the CRL4CRBN to selectively target GSPT1 for ubiquitination and proteasomal degradation. Depletion of GSPT1 by CC-90009 rapidly induces acute myeloid leukemia (AML) apoptosis, reducing leukemia engraftment and leukemia stem cells (LSCs) in large-scale primary patient xenografting of 35 independent AML samples, including those with adverse risk features. Using a genome-wide CRISPR-Cas9 screen for effectors of CC-90009 response, it was uncovered that the ILF2 and ILF3 heterodimeric complex as a novel regulator of cereblon expression. Knockout of ILF2/ILF3 decreases the production of full-length cereblon protein via modulating CRBN messenger RNA alternative splicing, leading to diminished response to CC-90009. The screen also revealed that the mTOR signaling and the integrated stress response specifically regulate the response to CC-90009 in contrast to other cereblon modulators. Hyperactivation of the mTOR pathway by inactivation of TSC1 and TSC2 protected against the growth inhibitory effect of CC-90009 by reducing CC-90009-induced binding of GSPT1 to cereblon and subsequent GSPT1 degradation. On the other hand, GSPT1 degradation promoted the activation of the GCN1/GCN2/ATF4 pathway and subsequent apoptosis in AML cells. Collectively, CC-90009 activity is mediated by multiple layers of signaling networks and pathways within AML blasts and LSCs, whose elucidation gives insight into further assessment of CC-90009s clinical utility. Reference: Blood. 2021 Feb 4;137(5):661-677. https://ashpublications.org/blood/article-lookup/doi/10.1182/blood.2020008676

In vivo activity:

CC-90009 effectively reduced tumor cell content in femur bone marrow in an HL-60 xenograft model of AML. Treatment was initiated 6 weeks postinoculation with vehicle and CC-90009. Treatment groups were terminated either on Day 7 (following 5 consecutive days of 5 mg/kg BID CC-90009) or on Day 11 (following 10 consecutive days of 2.5 mg/kg BID CC-90009) post treatment initiation. The primary end point for the study was percentage of hCD33+/CD45+ cells in the bone marrow by FACS analysis. Treatment with 5 mg/kg CC-90009 BIDx5 resulted in a significant (p = 0.0013) 54.0% reduction of human CD33+/CD45+ tumor cells in the BM when compared to the vehicle control group. Treatment with 2.5 mg/kg CC-90009 BIDx10 resulted in a significant (p < 0.0001) 71.5% reduction of human CD33+/CD45+ tumor cells in the bone marrow when compared to the vehicle control group. Reference: J Med Chem. 2021 Feb 25;64(4):1835-1843. https://doi.org/10.1021/acs.jmedchem.0c01489

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	216.52

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 461.85 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.

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

Formulation protocol:

In vitro protocol:

1. Hansen JD, Correa M, Alexander M, Nagy M, Huang D, Sapienza J, Lu G, LeBrun LA, Cathers BE, Zhang W, Tang Y, Ammirante M, Narla RK, Piccotti JR, Pourdehnad M, Lopez-Girona A. CC-90009: A Cereblon E3 Ligase Modulating Drug That Promotes Selective Degradation of GSPT1 for the Treatment of Acute Myeloid Leukemia. J Med Chem. 2021 Feb 25;64(4):1835-1843. doi: 10.1021/acs.jmedchem.0c01489. Epub 2021 Feb 16. PMID: 33591756. 2. Surka C, Jin L, Mbong N, Lu CC, Jang IS, Rychak E, Mendy D, Clayton T, Tindall E, Hsu C, Fontanillo C, Tran E, Contreras A, Ng SWK, Matyskiela M, Wang K, Chamberlain P, Cathers B, Carmichael J, Hansen J, Wang JCY, Minden MD, Fan J, Pierce DW, Pourdehnad M, Rolfe M, Lopez-Girona A, Dick JE, Lu G. CC-90009, a novel cereblon E3 ligase modulator, targets acute myeloid leukemia blasts and leukemia stem cells. Blood. 2021 Feb 4;137(5):661-677. doi: 10.1182/blood.2020008676. PMID: 33197925; PMCID: PMC8215192.

In vivo protocol:

1. Fang J, Pietzsch C, Tsaprailis G, Crynen G, Cho KF, Ting AY, Bukreyev A, de la Torre JC, Saphire EO. Functional interactomes of the Ebola virus polymerase identified by proximity proteomics in the context of viral replication. Cell Rep. 2022 Mar 22;38(12):110544. doi: 10.1016/j.celrep.2022.110544. PMID: 35320713; PMCID: PMC10496643. 2. Jochem M, Schrempf A, Wagner LM, Segal D, Cisneros J, Ng A, Winter GE, Krijgsveld J. Degradome analysis to identify direct protein substrates of small-molecule degraders. Cell Chem Biol. 2025 Jan 16;32(1):192-200.e6. doi: 10.1016/j.chembiol.2024.10.007. Epub 2024 Nov 12. PMID: 39536762. 3. Lier S, Sellmer A, Orben F, Heinzlmeir S, Krauß L, Schneeweis C, Hassan Z, Schneider C, Patricia Gloria Schäfer A, Pongratz H, Engleitner T, Öllinger R, Kuisl A, Bassermann F, Schlag C, Kong B, Dove S, Kuster B, Rad R, Reichert M, Wirth M, Saur D, Mahboobi S, Schneider G. A novel Cereblon E3 ligase modulator with antitumor activity in gastrointestinal cancer. Bioorg Chem. 2022 Feb;119:105505. doi: 10.1016/j.bioorg.2021.105505. Epub 2021 Nov 20. Erratum in: Bioorg Chem. 2024 May;146:107248. doi: 10.1016/j.bioorg.2024.107248. PMID: 34838332. 4. Sellar RS, Sperling AS, Słabicki M, Gasser JA, McConkey ME, Donovan KA, Mageed N, Adams DN, Zou C, Miller PG, Dutta RK, Boettcher S, Lin AE, Sandoval B, Quevedo Barrios VA, Kovalcik V, Koeppel J, Henderson EK, Fink EC, Yang L, Chan A, Pokharel SP, Bergstrom EJ, Burt R, Udeshi ND, Carr SA, Fischer ES, Chen CW, Ebert BL. Degradation of GSPT1 causes TP53-independent cell death in leukemia while sparing normal hematopoietic stem cells. J Clin Invest. 2022 Aug 15;132(16):e153514. doi: 10.1172/JCI153514. PMID: 35763353; PMCID: PMC9374383.