Description In vitro In vivo
ChemicalBook > CAS DataBase List > Pomalidomide

Pomalidomide

Description In vitro In vivo
Product Name
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;Pomalidomide;3-dioxo-2-(2
CBNumber
CB32128749
Molecular Formula
C13H11N3O4
Formula Weight
273.24
MOL File
19171-19-8.mol
More
Less

Pomalidomide Property

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
More
Less

Safety

WGK Germany 
3
RTECS 
NR3397905
HS Code 
29251900
Hazardous Substances Data
19171-19-8(Hazardous Substances Data)
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P0018
Product name
Pomalidomide
Purity
≥98% (HPLC)
Packaging
5mg
Price
$147
Updated
2024/03/01
Sigma-Aldrich
Product number
P0018
Product name
Pomalidomide
Purity
≥98%
Packaging
25mg
Price
$581
Updated
2024/03/01
TCI Chemical
Product number
P2074
Product name
Pomalidomide
Purity
>98.0%(HPLC)
Packaging
25mg
Price
$18
Updated
2024/03/01
TCI Chemical
Product number
P2074
Product name
Pomalidomide
Purity
>98.0%(HPLC)
Packaging
100mg
Price
$43
Updated
2024/03/01
Cayman Chemical
Product number
19877
Product name
Pomalidomide
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
More
Less

Pomalidomide Chemical Properties,Usage,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 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.

Uses

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

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

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.

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) Lopez-Girona?et al.?(2012),?Cereblon is direct protein target for immunomodulatory and antiproliferative activities of lenalidomide and pomalidomide; Leukemia,?26?2326 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) Donovan?et al.?(2018),?Thalidomide promotes degradation of SALL4, a transcription factor implicated in Duane Radial Ray syndrome; Elife,?7?e38430 4) Winter?et al.?(2015),?DRUG DEVELOPMENT. Phthalimide conjunction as a strategy for in vivo target protein degradation; Science,?348?1376 5) Lohbeck and Miller (2016),?Practical synthesis of a phthalimide-based Cereblon ligand to enable PROTAC development; Bioorg. Med. Chem. Lett.,?26?5260

Pomalidomide Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

Pomalidomide Suppliers

shandong XuanHong Pharmaceutical Technology Co.,Ltd
Tel
0531-88801869 15562622698
Fax
0531-88801867
Email
sciencechem@163.com
Country
China
ProdList
276
Advantage
55
Hebei mo Jin biotechnology co., ltd
Tel
15097329902
Fax
18503279000
Email
sales@hebeimojin.com
Country
China
ProdList
1633
Advantage
58
Durak (Jiangsu) Pharma Co., Ltd.
Tel
13512553699
Email
1374628507@qq.com
Country
China
ProdList
51
Advantage
58
Chongqing Botao Biotechnology Co., LTD
Tel
15223382610 15223382610
Email
danny@chemdad.com
Country
China
ProdList
1839
Advantage
58
Jiangxi taisinor Co., Ltd.
Tel
13576915071
Email
taisinor@vip.163.com
Country
China
ProdList
27
Advantage
58
Jinan Shengqi Pharmaceutical Co., Ltd
Tel
0531-88892685 18660160628
Email
2153390475@qq.com
Country
China
ProdList
198
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8415
Advantage
55
More
Less

View Lastest Price from Pomalidomide manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Pomalidomide 19171-19-8
Price
US $0.00/Kg/Bag
Min. Order
10g
Purity
99%min HPLC
Supply Ability
10KGS
Release date
2021-08-16
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Pomalidomide 19171-19-8
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-09-25
Hebei Chuanghai Biotechnology Co,.LTD
Product
Pomalidomide 19171-19-8
Price
US $19.00/KG
Min. Order
1KG
Purity
99.%
Supply Ability
50 ton
Release date
2024-08-19

19171-19-8, PomalidomideRelated Search:


  • 4-Amino-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione
  • Pomalidomide
  • Pomalidomide(CC-4047)
  • ActiMid
  • CC-4047
  • 4-AMino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
  • 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-d4
  • Pomalidomide, >=99%
  • Pomalidomid,4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
  • 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
  • pomalidomide,Pomalyst
  • Actimid (Celgene)
  • 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&gt
  • PomaL
  • Pomalidomide USP/EP/BP
  • 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
  • 19171-19-8
  • Inhibitor
  • Inhibitors
  • CC-4047