Mezigdomide | CAS#2259648-80-9 | Cereblon E3 ligase modulator

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

MedKoo CAT#: 207036

CAS#: 2259648-80-9

Description: Mezigdomide is a cereblon E3 ubiquitin ligase modulating agent with potential immunomodulating and antineoplastic activities. Mezigdomide specifically binds to cereblon (CRBN), thereby affecting the ubiquitin E3 ligase activity, and targeting certain substrate proteins for ubiquitination. This induces proteasome-mediated degradation of certain transcription factors, some of which are transcriptional repressors in T cells. This leads to modulation of the immune system, including activation of T lymphocytes, and downregulation of the activity of other proteins, some of which play key roles in the proliferation of certain cancer cell types.

Chemical Structure

Mezigdomide

CAS# 2259648-80-9

Instruction

Theoretical Analysis

MedKoo Cat#: 207036
Name: Mezigdomide
CAS#: 2259648-80-9
Chemical Formula: C32H30FN5O4
Exact Mass: 567.23
Molecular Weight: 567.621
Elemental Analysis: C, 67.71; H, 5.33; F, 3.35; N, 12.34; O, 11.27

Price and Availability

Size	Price	Availability
25mg	USD 450	2 Weeks
50mg	USD 750	2 Weeks
100mg	USD 1250	2 Weeks
200mg	USD 1950	2 Weeks
500mg	USD 2950	2 Weeks
1g	USD 4650	2 Weeks
2g	USD 6750	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Mezigdomide; CC-92480; CC 92480; CC92480;

IUPAC/Chemical Name: (S)-4-(4-(4-(((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-4-yl)oxy)methyl)benzyl)piperazin-1-yl)-3-fluorobenzonitrile

InChi Key: YTINZZFBHWSAGL-NDEPHWFRSA-N

InChi Code: InChI=1S/C32H30FN5O4/c33-26-16-23(17-34)8-9-27(26)37-14-12-36(13-15-37)18-21-4-6-22(7-5-21)20-42-29-3-1-2-24-25(29)19-38(32(24)41)28-10-11-30(39)35-31(28)40/h1-9,16,28H,10-15,18-20H2,(H,35,39,40)/t28-/m0/s1

SMILES Code: N#CC1=CC=C(N2CCN(CC3=CC=C(COC4=CC=CC5=C4CN([C@@H](CC6)C(NC6=O)=O)C5=O)C=C3)CC2)C(F)=C1

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: CRBN, the substrate recognition component of the CRL4-CRBN E3 ubiquitin ligase complex, plays a key role in the ubiquitination of certain proteins.

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 567.62 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:
In vivo protocol:

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1: Bourgeois W, Cutler JA, Aubrey BJ, Wenge D, Perner F, Martucci C, Henrich JA, Klega K, Nowak RP, Donovan KA, Boileau M, Wen Y, Hatton C, Apazidis AA, Olsen SN, Kirmani N, Pikman Y, Pollard JA, Perry JA, Sperling AS, Ebert BL, McGeehan GM, Crompton BD, Fischer ES, Armstrong SA. Mezigdomide is effective alone and in combination with Menin inhibition in pre-clinical models of KMT2A-r and NPM1c AML. Blood. 2023 Dec 14:blood.2023021105. doi: 10.1182/blood.2023021105. Epub ahead of print. PMID: 38096371.

2: Midha S, Hartley-Brown MA, Mo CC, Hossain S, Nadeem O, O'Donnell EK, Bianchi G, Sperling AS, Laubach JP, Richardson PG. A safety review of recently approved and emerging drugs for patients with relapsed or refractory multiple myeloma. Expert Opin Drug Saf. 2023 Jul-Dec;22(11):1049-1071. doi: 10.1080/14740338.2023.2274420. Epub 2023 Nov 28. PMID: 37906232.

3: Wu F, Liu L, Gaudy A, Wang X, Carayannopoulos L, Pourdehnad M, Lamba M. Model based assessment of food and acid reducing agent effects on oral absorption of mezigdomide (CC-92480), a novel cereblon E3 ligase modulator. CPT Pharmacometrics Syst Pharmacol. 2023 Oct;12(10):1473-1484. doi: 10.1002/psp4.13024. Epub 2023 Sep 13. PMID: 37705327; PMCID: PMC10583261.

4: Mezigdomide Data Show CELMoD Potential. Cancer Discov. 2023 Nov 1;13(11):2300. doi: 10.1158/2159-8290.CD-NB2023-0065. PMID: 37694945.

5: Richardson PG, Trudel S, Popat R, Mateos MV, Vangsted AJ, Ramasamy K, Martinez-Lopez J, Quach H, Orlowski RZ, Arnao M, Lonial S, Karanes C, Pawlyn C, Kim K, Oriol A, Berdeja JG, Rodríguez Otero P, Casas-Avilés I, Spirli A, Poon J, Li S, Gong J, Wong L, Lamba M, Pierce DW, Amatangelo M, Peluso T, Maciag P, Katz J, Pourdehnad M, Bahlis NJ; CC-92480-MM-001 Study Investigators. Mezigdomide plus Dexamethasone in Relapsed and Refractory Multiple Myeloma. N Engl J Med. 2023 Sep 14;389(11):1009-1022. doi: 10.1056/NEJMoa2303194. Epub 2023 Aug 30. PMID: 37646702.

6: Shortt J. Mezigdomide and Multiple Myeloma. N Engl J Med. 2023 Sep 14;389(11):1046-1050. doi: 10.1056/NEJMe2307370. Epub 2023 Aug 30. PMID: 37646699.

7: Richardson PG, Mateos MV, Vangsted AJ, Ramasamy K, Abildgaard N, Ho PJ, Quach H, Bahlis NJ. The role of E3 ubiquitin ligase in multiple myeloma: potential for cereblon E3 ligase modulators in the treatment of relapsed/refractory disease. Expert Rev Proteomics. 2022 Apr-Jun;19(4-6):235-246. doi: 10.1080/14789450.2022.2142564. Epub 2022 Nov 9. PMID: 36342226.

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