CC-122
- Product Name
- CC-122
- CAS No.
- 1015474-32-4
- Chemical Name
- CC-122
- Synonyms
- CC-122;CS-2428;Avadomide;CC122;CC 122;Avadomide(CC-122);CC122 (Avadomide);AVADOMIDE;CC122;CC 122;Avadomide, 10 mM in DMSO;Avadomide (Synonyms: CC 122);3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione
- CBNumber
- CB73137081
- Molecular Formula
- C14H14N4O3
- Formula Weight
- 286.29
- MOL File
- 1015474-32-4.mol
CC-122 Property
- Melting point:
- > 270°C (dec.)
- Density
- 1.58±0.1 g/cm3(Predicted)
- storage temp.
- Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- pka
- 10.66±0.40(Predicted)
- form
- Solid
- color
- Pale Beige
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P321Specific treatment (see … on this label).
P330Rinse mouth.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
P403+P233Store in a well-ventilated place. Keep container tightly closed.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 26257
- Product name
- CC-122
- Packaging
- 1mg
- Price
- $64
- Updated
- 2024/03/01
- Product number
- 26257
- Product name
- CC-122
- Packaging
- 25mg
- Price
- $1006
- Updated
- 2024/03/01
- Product number
- 26257
- Product name
- CC-122
- Packaging
- 5mg
- Price
- $280
- Updated
- 2024/03/01
- Product number
- 26257
- Product name
- CC-122
- Packaging
- 10mg
- Price
- $497
- Updated
- 2024/03/01
- Product number
- A614995
- Product name
- 3-(5-Amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione
- Packaging
- 100mg
- Price
- $300
- Updated
- 2021/12/16
CC-122 Chemical Properties,Usage,Production
Description
3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione has been shown to treat Diffuse large B-cell lymphoma with antitumor and immunomodulatory activity. Its molecular target is the protein cereblon, a substrate receptor of the cullin ring E3 ubiquitin ligase complex CRL4.
Uses
Avadomide is an orally active cereblon modulator. Avadomide modulates cereblon E3 ligase activity, inhibits NF-κB pathway, arrests the cell cycle at G1 phase, and thus induces apoptosis in cancer cell PDAC. Avadomide exhibits potent antitumor and immunomodulatory activities[1][2][3].
Synthesis
1015474-86-8
1015474-32-4
General procedure for the synthesis of 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione from RSYY (niraparib intermediate)-14: To a stirred mixture of 2-amino-6-nitrobenzoic acid (25-1) (1 g, 5.49 mmol) and imidazole (1.2 equiv) in acetonitrile (10 mL) was added acetyl chloride (25-2) (469 μL) and then the reaction mixture was stirred overnight. 3-Aminopiperidine-2,6-dione hydrochloride (903 mg, 5.49 mmol) was then added and supplemented with the addition of the remaining base to bring the total imidazole amount to 1.34 g (19.7 mmol). Triphenyl phosphite (1.72 mL, 6.58 mmol) was then added and the reaction mixture was refluxed for two days. After cooling to room temperature, 40 mL of water was added to slowly form a suspension, which was filtered and washed sequentially with water and EtOAc. The solid product 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione (1-2) was obtained by isolation (953 mg, 3.01 mmol, 55.0% yield). lc/ms (es+): m/z 317 [M+H]+. 3-(2-methyl-5-nitro-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione (25-3) (690 mg, 2.18 mmol) was dissolved in 10 mL of anhydrous DMF, carbon-loaded dihydroxypalladium (306 mg, 0.218 mmol) at 50% humidity was added, and the mixture was purged with nitrogen for 15 min, followed by three cycles of replacement with hydrogen at a 1 atm hydrogen pressure for overnight reaction. Upon completion of the reaction, the palladium catalyst was removed by filtration through a diatomaceous earth pad, and the filtrate was concentrated and purified by an ISCO system using a MeOH/DCM solvent mixture to afford the target product, 3-(5-amino-2-methyl-4-oxoquinazolin-3(4H)-yl)piperidine-2,6-dione (25-4) (498 mg, 1.73 mmol, 79.8% yield), as an off-white solid.LC/MS (ES+): m/z 287 [M+H]+.
in vivo
Treatment of female CB-17 SCID mice with Avadomide (CC122) at 3 or 30 mg/kg once daily significantly decreased tumor growth in OCI-LY10 ABC-DLBCL (P = .028 and P < .001, respectively) and WSU-DLCL2 GCB-DLBCL derived xenograft models (P < .01) compared with the vehicle control. In a separate study, we assessed the ability of Avadomide (CC122) to promote degradation of Ikaros and Aiolos in vivo. In the 21-day efficacy study of WSU-DLCL2 xenograft transplanted mice, tumors were excised 1, 6, or 24 hours post final dosing. Aiolos and Ikaros expression was interrogated through immunohistochemistry (IHC) and was found to be decreased 64% and 30%, respectively, compared with vehicle within 1 hour of treatment, with a maximal reduction of 94% and 69%, respectively, observed at 6 hours. Aiolos and Ikaros levels partially recovered 24 hours postdosing with protein level within 20% and 34% of vehicle, respectively. The 24-hour postdose Aiolos and Ikaros expression represents the trough compound level following multiple doses of Avadomide (CC122). When the 1-hour time point is compared with the 24-hour postdose time point, there is a significant reduction in Aiolos but not Ikaros expression; however, at the 6-hour time point, both transcription factors are significantly different from the 24-hour time point. Taken together, these data reveal that Avadomide (CC122) inhibited DLBCL tumor growth in vivo and that this activity was associated with the degradation of Aiolos and Ikaros in both ABC- and GCB-DLBCL xenograft models[1].
References
[1] Rasco DW, et al. A First-in-Human Study of Novel Cereblon Modulator Avadomide (CC-122) in Advanced Malignancies. Clin Cancer Res. 2019 Jan 1;25(1):90-98. DOI:10.1158/1078-0432.CCR-18-1203
[2] Hagner, P.R.et al.CC-122, a pleiotropic pathway modifier, mimics an IFN response and has antitumor activity in DLBCL.Blood.Aug 6;126(6):779-89. DOI:10.1182/blood-2015-02-628669
[3] Nishi H, et al., Anti-tumor effect of avadomide in gemcitabine-resistant pancreatic ductal adenocarcinoma. Cancer Chemother Pharmacol. 2023 Oct;92(4):303-314. DOI:10.1007/s00280-023-04531-w
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View Lastest Price from CC-122 manufacturers
- Product
- CC-122 1015474-32-4
- Price
- US $0.01/KG
- Min. Order
- 1KG
- Purity
- 98%; 99%
- Supply Ability
- 1kg; 10kg; 25kg
- Release date
- 2020-01-07