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19171-19-8

19171-19-8 Structure

19171-19-8 Structure
IdentificationBack Directory
[Name]

4-Amino-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione
[CAS]

19171-19-8
[Synonyms]

IMiD 3
ActiMid
CC-4047
Pomalidomide
Pomalidomide-d4
Pomalidomide(CC-4047)
Pomalidomide(CC-4047,Actimid)
3-amino-N-(2,6-dioxo-3-piperidyl)phthalamide
3-Amino-N-(2,6-dioxo-3-piperidyl)phthalimide
4-Amino-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione
4-AMino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline
4-Amino-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
1H-Isoindole-1,3(2H)-dione,4-aMino-2-(2,6-dioxo-3-piperidinyl)-
[EINECS(EC#)]

805-902-5
[Molecular Formula]

C13H11N3O4
[MDL Number]

MFCD12756407
[MOL File]

19171-19-8.mol
[Molecular Weight]

273.24
Chemical PropertiesBack Directory
[Melting point ]

318.5 - 320.5°
[Boiling point ]

582.9±45.0 °C(Predicted)
[density ]

1.570±0.06 g/cm3(Predicted)
[storage temp. ]

2-8°C
[solubility ]

DMSO: ≥14mg/mL
[form ]

powder
[pka]

10.75±0.40(Predicted)
[color ]

yellow
[Merck ]

14,135
[InChIKey]

UVSMNLNDYGZFPF-UHFFFAOYSA-N
Hazard InformationBack Directory
[Chemical Properties]

Yellow Solid
[Usage]

Pomalidomide inhibits LPS-induced TNF-α release with IC50 of 13 nM
[Usage]

Pomalidomide is a second generation immunomodulator, TNF-α inhibitor, and thalidomide analog. An inhibitor of LPS-induced TNFαrelease.
[Usage]

Pomalidomide is a thalidomide derivative, a potent inhibitor of TNF-α production. It is an antiinflammatory and antitumor agent used in the treatment of multiple myeloma.
[Originator]

Celgene Corporation (United States)
[Uses]

Pomalidomide inhibits LPS-induced TNF-α release with IC50 of 13 nM
[Uses]

Pomalidomide is a thalidomide derivative, a potent inhibitor of TNF-α production. It is an antiinflammatory and antitumor agent used in the treatment of multiple myeloma.
[Uses]

Pomalidomide is a second generation immunomodulator, TNF-α inhibitor, and thalidomide analog. An inhibitor of LPS-induced TNFαrelease.
[Definition]

ChEBI: An aromatic amine that is thalidomide substituted at position 4 on the isoindole ring system by an amino group. Used for the treatment of multiple myeloma in patients who failed to respond to previous therapies.
[Brand name]

Pomalyst
[Chemical Synthesis]

First, condensation of commercially available 3-nitrophthalic anhydride (133) and L-glutamine in warm DMF gave nitrophthalimide 134. Although the authors from Celgene do not explicitly describe the racemization of the stereocenter derived from L-glutamine, scrambling of the stereocenter has been reported during this step under neutral conditions at elevated temperatures. Next, hydrogenative reduction of the nitro group furnished the anilinophthalimide 135, and this was followed by treatment with CDI in refluxing acetonitrile to secure the piperidone dione and ultimately furnish pomalidomide (XVIII) as the racemate in 87% overall yield from 134.

Safety DataBack Directory
[WGK Germany ]

3
[RTECS ]

NR3397905
[HS Code ]

29251900
[Hazardous Substances Data]

19171-19-8(Hazardous Substances Data)
Questions And AnswerBack Directory
[Description]

Pomalidomide inhibits LPS-induced TNF-α release with IC50 of 13 nM in PBMCs.
[In vitro]

Pomalidomide inhibits lipopolysaccharide (LPS) stimulated TNF-alpha release in human PBMC and in human whole blood with IC50 values of 13 nM and 25 nM, respectively. Pomalidomide inhibits the growth of T regulatory cells which is stimulated by IL-2 with an IC50 of ~1 μM. Treatment with Pomalidomide (6.4 nM-10 μM) increases the production of IL-2 in human peripheral blood T cells, and is slightly more potent in the CD4+ subset than in the CD8+ subset. Pomalidomide is significantly more potent than CC-5013 at elevating IL-2, IL-5, and IL-10 levels, but only slightly more potent than CC-5013 at elevating IFN-γ levels.
Pomalidomide enhances SEE and Raji cells induced AP-1 transcriptional activity in Jurkat cells in a dose-dependent manner, with a maximal enhancement of 4-fold at 1 μM. Exposure of Raji cells to various concentrations of Pomalidomide (2.5-40 μg/mL) for 48 hours leads to a significant decrease in cell proliferation and DNA synthesis. There is a reduction of ~40% compared to vehicle-treated controls.
[In vivo]

Pomalidomide enhances the antitumor effect of rituximab against B-cell lymphomas in severe combined immunodeficient mice. Administration of Pomalidomide in combination with rituximab, gives the mice a median survival period of 74 days compared with 58 days of CC5013/rituximab treatment and 45 days of rituximab nonotherapy. The synergistic effect of Pomalidomide and rituximab can be completely abrogated by depletion of NK cells, supporting the proposal that NK cell expansion is one mechanism by which Pomalidomide may augment rituximab antitumor activity.
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