Pomalidomide
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MedKoo CAT#: 202310

CAS#: 19171-19-8

Description: Pomalidomide, also known as CC4047, is an orally bioavailable derivative of thalidomide with potential immunomodulating, antiangiogenic and antineoplastic activities. Although its exact mechanism of action has yet to be fully elucidated, pomalidomide appears to inhibit TNF-alpha production, enhance the activity of T cells and natural killer (NK) cells and enhance antibody-dependent cellular cytotoxicity (ADCC). Pomalidomide was approved on February 8, 2013 as a treatment for relapsed and refractory multiple myeloma.

Chemical Structure

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Pomalidomide
CAS# 19171-19-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202310
Name: Pomalidomide
CAS#: 19171-19-8
Chemical Formula: C13H11N3O4
Exact Mass: 273.07
Molecular Weight: 273.240
Elemental Analysis: C, 57.14; H, 4.06; N, 15.38; O, 23.42

Price and Availability

Size Price Availability Quantity
500mg USD 90 Ready to ship
1g USD 150 Ready to ship
2g USD 225 Ready to ship
5g USD 450 Ready to ship
10g USD 800 Ready to ship
20g USD 1450 Ready to ship
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Synonym: CC4047; CC 4047; CC-4047; Pomalidomide. Brand name: Pomalyst.

IUPAC/Chemical Name: 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

InChi Key: UVSMNLNDYGZFPF-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H11N3O4/c14-7-3-1-2-6-10(7)13(20)16(12(6)19)8-4-5-9(17)15-11(8)18/h1-3,8H,4-5,14H2,(H,15,17,18)

SMILES Code: O=C1N(C(CC2)C(NC2=O)=O)C(C3=C1C=CC=C3N)=O

Appearance: white 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: >2 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:

Biological target: Pomalidomide is the third-generation immunomodulatory agent, functions through interacting with the E3 ligase cereblon and induces degradation of essential Ikaros transcription factors.
In vitro activity: Here, treatment of PEL cells with Pom (Pomalidomide) restores NK cell lysis and T-cell activation, and this is directly due to the upregulation of the co-stimulatory molecules ICAM-1 and B7-2, as specific blocking antibodies to these proteins prevent the responses. To this study’s knowledge, this is the first report of otherwise “immunologically silent” PELs being specifically sensitized for recognition and lysis by T-cells and NK-cells, both of which are important components of anti-tumor immunity. The mechanistic studies further provide evidence that these effects occur through Pom’s effects on the E3 ubiquitin ligase cereblon and, at least in part, involve the PI3K pathway. Reference: PLoS Pathog. 2021 Jan; 17(1): e1009091. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7817053/
In vivo activity: POM (Pomalidomide) showed a negative impact on proliferation of Raji and OCI-LY10 cells (Figure 2) and significant preclinical therapeutic activity against CNS lymphoma in both Raji and OCI-LY10 murine orthotopic models. The in vivo findings showed a dose-dependent therapeutic activity against CNS lymphoma with statistically significant therapeutic activity at 3 mg, 10 mg, and 30 mg/kg dose levels of POM in terms of reduction of tumor growth and prolongation of survival (Figure 3). Reference: PLoS One. 2013; 8(8): e71754. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3734315/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 15.0 54.90

Preparing Stock Solutions

The following data is based on the product molecular weight 273.24 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
Formulation protocol: 1. Shrestha P, Davis DA, Jaeger HK, Stream A, Aisabor AI, Yarchoan R. Pomalidomide restores immune recognition of primary effusion lymphoma through upregulation of ICAM-1 and B7-2. PLoS Pathog. 2021 Jan 7;17(1):e1009091. doi: 10.1371/journal.ppat.1009091. PMID: 33411730; PMCID: PMC7817053. 2. Davis DA, Shrestha P, Aisabor AI, Stream A, Galli V, Pise-Masison CA, Tagawa T, Ziegelbauer JM, Franchini G, Yarchoan R. Pomalidomide increases immune surface marker expression and immune recognition of oncovirus-infected cells. Oncoimmunology. 2018 Dec 5;8(2):e1546544. doi: 10.1080/2162402X.2018.1546544. PMID: 30713808; PMCID: PMC6343774. 3. Casu MA, Mocci I, Isola R, Pisanu A, Boi L, Mulas G, Greig NH, Setzu MD, Carta AR. Neuroprotection by the Immunomodulatory Drug Pomalidomide in the Drosophila LRRK2WD40 Genetic Model of Parkinson's Disease. Front Aging Neurosci. 2020 Feb 13;12:31. doi: 10.3389/fnagi.2020.00031. PMID: 32116655; PMCID: PMC7031158. 4. Li Z, Qiu Y, Personett D, Huang P, Edenfield B, Katz J, Babusis D, Tang Y, Shirely MA, Moghaddam MF, Copland JA, Tun HW. Pomalidomide shows significant therapeutic activity against CNS lymphoma with a major impact on the tumor microenvironment in murine models. PLoS One. 2013 Aug 5;8(8):e71754. doi: 10.1371/journal.pone.0071754. PMID: 23940785; PMCID: PMC3734315.
In vitro protocol: 1. Shrestha P, Davis DA, Jaeger HK, Stream A, Aisabor AI, Yarchoan R. Pomalidomide restores immune recognition of primary effusion lymphoma through upregulation of ICAM-1 and B7-2. PLoS Pathog. 2021 Jan 7;17(1):e1009091. doi: 10.1371/journal.ppat.1009091. PMID: 33411730; PMCID: PMC7817053. 2. Davis DA, Shrestha P, Aisabor AI, Stream A, Galli V, Pise-Masison CA, Tagawa T, Ziegelbauer JM, Franchini G, Yarchoan R. Pomalidomide increases immune surface marker expression and immune recognition of oncovirus-infected cells. Oncoimmunology. 2018 Dec 5;8(2):e1546544. doi: 10.1080/2162402X.2018.1546544. PMID: 30713808; PMCID: PMC6343774.
In vivo protocol: 1. Casu MA, Mocci I, Isola R, Pisanu A, Boi L, Mulas G, Greig NH, Setzu MD, Carta AR. Neuroprotection by the Immunomodulatory Drug Pomalidomide in the Drosophila LRRK2WD40 Genetic Model of Parkinson's Disease. Front Aging Neurosci. 2020 Feb 13;12:31. doi: 10.3389/fnagi.2020.00031. PMID: 32116655; PMCID: PMC7031158. 2. Li Z, Qiu Y, Personett D, Huang P, Edenfield B, Katz J, Babusis D, Tang Y, Shirely MA, Moghaddam MF, Copland JA, Tun HW. Pomalidomide shows significant therapeutic activity against CNS lymphoma with a major impact on the tumor microenvironment in murine models. PLoS One. 2013 Aug 5;8(8):e71754. doi: 10.1371/journal.pone.0071754. PMID: 23940785; PMCID: PMC3734315.

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1: Elkinson S, McCormack PL. Pomalidomide: First Global Approval. Drugs. 2013 Apr 10. [Epub ahead of print] PubMed PMID: 23572409.

2: Traynor K. Pomalidomide approved for multiple myeloma. Am J Health Syst Pharm. 2013 Mar 15;70(6):474. doi: 10.2146/news130020. PubMed PMID: 23456394.

3: Henry JY, Labarthe MC, Meyer B, Dasgupta P, Dalgleish AG, Galustian C. Enhanced cross-priming of naive CD8+ T cells by DCs treated by the IMiDs(®) immunomodulatory compounds Lenalidomide and Pomalidomide. Immunology. 2013 Feb 1. doi: 10.1111/imm.12087. [Epub ahead of print] PubMed PMID: 23374145.

4: Ellis PM, Jungnelius U, Zhang J, Fandi A, Beck R, Shepherd FA. A Phase I Study of Pomalidomide (CC-4047) in Combination with Cisplatin and Etoposide in Patients with Extensive-Stage Small-Cell Lung Cancer. J Thorac Oncol. 2013 Apr;8(4):423-8. doi: 10.1097/JTO.0b013e318282707b. PubMed PMID: 23370364.

5: Leleu X, Attal M, Arnulf B, Moreau P, Traulle C, Marit G, Mathiot C, Petillon MO, Macro M, Roussel M, Pegourie B, Kolb B, Stoppa AM, Hennache B, Bréchignac S, Meuleman N, Thielemans B, Garderet L, Royer B, Hulin C, Benboubker L, Decaux O, Escoffre-Barbe M, Michallet M, Caillot D, Fermand JP, Avet-Loiseau H, Facon T; Intergroupe Francophone du Myélome. Pomalidomide plus low-dose dexamethasone is active and well tolerated in bortezomib and lenalidomide-refractory multiple myeloma: Intergroupe Francophone du Myelome 2009-02. Blood. 2013 Mar 14;121(11):1968-75. doi: 10.1182/blood-2012-09-452375. Epub 2013 Jan 14. PubMed PMID: 23319574.

6: Richardson PG, Siegel D, Baz R, Kelley SL, Munshi NC, Laubach J, Sullivan D, Alsina M, Schlossman R, Ghobrial IM, Doss D, Loughney N, McBride L, Bilotti E, Anand P, Nardelli L, Wear S, Larkins G, Chen M, Zaki MH, Jacques C, Anderson KC. Phase 1 study of pomalidomide MTD, safety, and efficacy in patients with refractory multiple myeloma who have received lenalidomide and bortezomib. Blood. 2013 Mar 14;121(11):1961-7. doi: 10.1182/blood-2012-08-450742. Epub 2012 Dec 14. PubMed PMID: 23243282.

7: Hoffmann M, Kasserra C, Reyes J, Schafer P, Kosek J, Capone L, Parton A, Kim-Kang H, Surapaneni S, Kumar G. Absorption, metabolism and excretion of [14C]pomalidomide in humans following oral administration. Cancer Chemother Pharmacol. 2013 Feb;71(2):489-501. doi: 10.1007/s00280-012-2040-6. Epub 2012 Dec 1. PubMed PMID: 23203815; PubMed Central PMCID: PMC3556473.

8: Bolzoni M, Storti P, Bonomini S, Todoerti K, Guasco D, Toscani D, Agnelli L, Neri A, Rizzoli V, Giuliani N. Immunomodulatory drugs lenalidomide and pomalidomide inhibit multiple myeloma-induced osteoclast formation and the RANKL/OPG ratio in the myeloma microenvironment targeting the expression of adhesion molecules. Exp Hematol. 2012 Nov 23. doi:pii: S0301-472X(12)00542-5. 10.1016/j.exphem.2012.11.005. [Epub ahead of print] PubMed PMID: 23178378.

9: Ruchelman AL, Man HW, Zhang W, Chen R, Capone L, Kang J, Parton A, Corral L, Schafer PH, Babusis D, Moghaddam MF, Tang Y, Shirley MA, Muller GW. Isosteric analogs of lenalidomide and pomalidomide: synthesis and biological activity. Bioorg Med Chem Lett. 2013 Jan 1;23(1):360-5. doi: 10.1016/j.bmcl.2012.10.071. Epub 2012 Oct 27. PubMed PMID: 23168019.

10: Zhu YX, Kortuem KM, Stewart AK. Molecular mechanism of action of immune-modulatory drugs thalidomide, lenalidomide and pomalidomide in multiple myeloma. Leuk Lymphoma. 2013 Apr;54(4):683-7. doi: 10.3109/10428194.2012.728597. Epub 2012 Sep 28. PubMed PMID: 22966948.