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Pomalidomide

CAS No.
19171-19-8
Chemical Name:
Pomalidomide
Synonyms
4-AMino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione;CC-4047;Pomadomide;Pomalidomide-d4;PomaL;IMiD 3;CS-388;ActiMid;Pomalomide;Pomalidomide
CBNumber:
CB32128749
Molecular Formula:
C13H11N3O4
Molecular Weight:
273.24
MDL Number:
MFCD12756407
MOL File:
19171-19-8.mol
MSDS File:
SDS
Last updated:2024-12-04 20:40:58

Pomalidomide Properties

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
pka 10.75±0.40(Predicted)
form powder
color yellow
Merck 14,135
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChI 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)
InChIKey UVSMNLNDYGZFPF-UHFFFAOYSA-N
SMILES C1(=O)C2=C(C(N)=CC=C2)C(=O)N1C1CCC(=O)NC1=O
NCI Dictionary of Cancer Terms CC-4047; pomalidomide
FDA UNII D2UX06XLB5
NCI Drug Dictionary pomalidomide
ATC code L04AX06

Pharmacokinetic data

Protein binding 12-44%
Excreted unchanged in urine 2 (73% plus metabolites)
Volume of distribution 62-138 Litres
Biological half-life 9.5 (healthy), 7.5 (myeloma) / Not significantly changed

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H360D
Precautionary statements  P201-P202-P280-P308+P313-P405-P501
WGK Germany  3
RTECS  NR3397905
HS Code  29251900
Hazardous Substances Data 19171-19-8(Hazardous Substances Data)
NFPA 704
0
1 0

Pomalidomide price More Price(61)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P0018 Pomalidomide ≥98% (HPLC) 19171-19-8 5mg $147 2024-03-01 Buy
Sigma-Aldrich P0018 Pomalidomide ≥98% 19171-19-8 25mg $581 2024-03-01 Buy
TCI Chemical P2074 Pomalidomide >98.0%(HPLC) 19171-19-8 25mg $18 2024-03-01 Buy
TCI Chemical P2074 Pomalidomide >98.0%(HPLC) 19171-19-8 100mg $43 2024-03-01 Buy
Cayman Chemical 19877 Pomalidomide ≥98% 19171-19-8 1mg $32 2024-03-01 Buy
Product number Packaging Price Buy
P0018 5mg $147 Buy
P0018 25mg $581 Buy
P2074 25mg $18 Buy
P2074 100mg $43 Buy
19877 1mg $32 Buy

Pomalidomide Chemical Properties,Uses,Production

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.

Description

In February 2013, the US FDA approved pomalidomide (also known as CC4047) for the treatment of multiple myeloma (MM) in patients with disease progression after receiving other cancer therapeutics. Pomalidomide is a 4-amino analog of thalidomide with enhanced potency and an improved toxicity profile. Pomalidomide and thalidomide exert their effects by modulation of immunity, inhibition of angiogenesis, interference with the bone/tumor microenvironment, and inhibition of the cereblon protein. Pomalidomide potently inhibited in vitro proliferation in a variety of human MM cell lines, IC50~10 nM, while thalidomide showed almost no inhibition up to 100 μM. In mouse MM tumor models, 50 mg/kg daily doses of pomalidomide resulted in marked inhibition of tumor growth after 15 days of treatment and complete regression in 3–6 weeks versus thalidomide-treated controls at the same dose. Pomalidomide is prepared by condensation of 4-nitrophthalic anhydride with 3-aminopiperidine-2,6-dione followed by catalytic hydrogenation of the nitro group.

Chemical Properties

Yellow Solid

Originator

Celgene Corporation (United States)

Uses

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

Uses

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

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.

Definition

ChEBI: Pomalidomide is 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. It has a role as an antineoplastic agent, an immunomodulator and an angiogenesis inhibitor. It is a dicarboximide, a member of isoindoles, a member of piperidones and an aromatic amine. It is functionally related to a thalidomide.

brand name

Pomalyst

Biochem/physiol Actions

Pomalidomide is an effective fetal hemoglobin (HbF) inducer that downregulates the key γ-globin repressors, SRY-box transcription factor 6 (SOX6), and BAF chromatin remodeling complex subunit (BCL11A).

Clinical Use

Treatment of multiple myeloma

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.

Synthesis_19171-19-8

target

TNF-α

Drug interactions

Potentially hazardous interactions with other drugs
Antidepressants: concentration increased by fluvoxamine.

Metabolism

Mainly metabolised in the liver by the cytochrome P450 isoenzymes CYP1A2 and CYP3A4, with CYP2C19 and CYP2D6 playing a minor role.
Following a single oral administration of [14C]-pomalidomide (2 mg) to healthy subjects, approximately 73% and 15% of the radioactive dose was eliminated in urine and faeces, respectively, with approximately 2% and 8% of the dosed radiocarbon eliminated as pomalidomide in urine and faeces.

storage

Store at +4°C

References

1) A LOPEZ-GIRONA. Cereblon is a direct protein target for immunomodulatory and antiproliferative activities of lenalidomide and pomalidomide[J]. Leukemia, 2012, 26 11: 2326-2335. DOI:10.1038/leu.2012.119.
2) Zhu?et al.?(2013),?Molecular mechanism of action of immune-modulatory drugs thalidomide, lenalidomide and pomalidomide in multiple myeloma; Leukemia Lymphoma,?54?683
3) KATHERINE A DONOVAN. Thalidomide promotes degradation of SALL4, a transcription factor implicated in Duane Radial Ray syndrome.[J]. eLife, 2018. DOI:10.7554/eLife.38430.
4) Winter?et al.?(2015),?DRUG DEVELOPMENT. Phthalimide conjunction as a strategy for in vivo target protein degradation; Science,?348?1376
5) JASMIN LOHBECK Aubry K M. Practical synthesis of a phthalimide-based Cereblon ligand to enable PROTAC development[J]. Bioorganic & Medicinal Chemistry Letters, 2016, 26 21: Pages 5260-5262. DOI:10.1016/j.bmcl.2016.09.048.

340020-02-2
2353-44-8
19171-19-8
Synthesis of Pomalidomide from 2H-Isoindole-2-carboxylic acid, 4-amino-1,3-dihydro-1,3-dioxo-, ethyl ester and 3-aminopiperidine-2,6-dione
Global( 508)Suppliers
Supplier Tel Email Country ProdList Advantage
Beijing Mesochem Technology Co.,Ltd
+8613651027935 rachel@mesochem.com China 191 58
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Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497 sales01@cooperate-pharm.com CHINA 1803 55

View Lastest Price from Pomalidomide manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Pomalidomide pictures 2024-12-23 Pomalidomide
19171-19-8
US $0.00 / g 1g More Than 99% 100kg/Month BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Pomalidomide pictures 2024-12-13 Pomalidomide
19171-19-8
US $0.00 / Kg/Bag 10g 99%min HPLC 10KGS WUHAN FORTUNA CHEMICAL CO., LTD
Pomalidomide pictures 2024-12-04 Pomalidomide
19171-19-8
US $10.00 / KG 1KG 99% 10 mt Hebei Weibang Biotechnology Co., Ltd
  • Pomalidomide pictures
  • Pomalidomide
    19171-19-8
  • US $0.00 / g
  • More Than 99%
  • BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
  • Pomalidomide pictures
  • Pomalidomide
    19171-19-8
  • US $0.00 / Kg/Bag
  • 99%min HPLC
  • WUHAN FORTUNA CHEMICAL CO., LTD
  • Pomalidomide pictures
  • Pomalidomide
    19171-19-8
  • US $10.00 / KG
  • 99%
  • Hebei Weibang Biotechnology Co., Ltd

Pomalidomide Spectrum

4-Amino-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione Pomalidomide Pomalidomide(CC-4047) ActiMid 1H-Isoindole-1,3(2H)-dione,4-aMino-2-(2,6-dioxo-3-piperidinyl)- Pomalidomide(CC-4047,Actimid) 1,3-dioxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline 3-amino-N-(2,6-dioxo-3-piperidyl)phthalamide 4-Amino-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione IMiD 3 Pomalidomide, >=99% Pomalidomid,4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione pomalidomide,Pomalyst Actimid (Celgene) 3-dioxo-2-(2 6-dioxopiperidin-3-yl)-4-aminoisoindoline Pomalidomide high quality 4-Amino-2-(2,6-dioxo-3-piperidinyl)isoindole-1,3-dione CS-388 4-Amino-2-(2,6-dioxo-piperidin-3-yl)-1H-isoindol-1,3(2H)-dione 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindole-1,3-dione Pomalidomide high quality 19171-19-8 Pomalidomide, 99%, a inhibitor of TNF-α Pomalidomide> PomaL Pomalidomide USP/EP/BP CC-4047 4-AMino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione Pomalidomide-d4 Pomadomide Pomaduramide QTARK(Me3)T-PEG4-Acp-Pomalidomide /Pomalidomide Pomalidomide (CC4047 or actimid) 4-Amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione (pomalidomide) 4-amino-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione Pomalomide 19171-19-8 Inhibitor Inhibitors CC-4047