Pomalidomide | 19171-19-8

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)

GHS08

Signal word

Danger

Hazard statements

H360D

Precautionary statements

P201-P202-P280-P308+P313-P405-P501

WGK Germany

3

RTECS

NR3397905

HS Code

29251900

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.

Pomalidomide synthesis

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

Pomalidomide Preparation Products And Raw materials

Raw materials

2H-Isoindole-2-carboxylic acid, 4-amino-1,3-dihydro-1,3-dioxo-, ethyl ester 2,6-Dioxopiperidine-3-ammonium chloride 3-aminopiperidine-2,6-dione 2-(2,6-dioxopiperidin-3-yl)-4-nitroisoindoline-1,3-dione 3-AMINOPHTHALIC ACID HYDROCHLORIDE

1,1'-Carbonyldiimidazole

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Preparation Products

Pomalidomide Suppliers

Global( 514)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Beijing Mesochem Technology Co.,Ltd	+8613651027935	rachel@mesochem.com	China	191	58
Hebei Chuanghai Biotechnology Co,.LTD	+86-13131129325	sales1@chuanghaibio.com	China	5893	58
shandong perfect biotechnology co.ltd	+86-53169958659 +86-13153181156	sales@sdperfect.com	China	294	58
Henan Bao Enluo International TradeCo.，LTD	+86-17331933971 +86-17331933971	deasea125996@gmail.com	China	2472	58
Shaanxi Haibo Biotechnology Co., Ltd	+undefined18602966907	qinhe02@xaltbio.com	China	997	58
Shaanxi TNJONE Pharmaceutical Co., Ltd	+8618092446649	sarah@tnjone.com	China	1143	58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.	+86-18600796368 +86-18600796368	sales@sjar-tech.com	China	444	58
Capot Chemical Co.,Ltd.	+86-（0）57185586718 +86-13336195806	sales@capot.com	China	29791	60
Beijing Cooperate Pharmaceutical Co.,Ltd	010-60279497	sales01@cooperate-pharm.com	CHINA	1803	55
Henan Tianfu Chemical Co.,Ltd.	+86-0371-55170693 +86-19937530512	info@tianfuchem.com	China	21634	55

Supplier	Advantage
Beijing Mesochem Technology Co.,Ltd	58
Hebei Chuanghai Biotechnology Co,.LTD	58
shandong perfect biotechnology co.ltd	58
Henan Bao Enluo International TradeCo.，LTD	58
Shaanxi Haibo Biotechnology Co., Ltd	58
Shaanxi TNJONE Pharmaceutical Co., Ltd	58
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.	58
Capot Chemical Co.,Ltd.	60
Beijing Cooperate Pharmaceutical Co.,Ltd	55
Henan Tianfu Chemical Co.,Ltd.	55

View Lastest Price from Pomalidomide manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-22	Pomalidomide 19171-19-8	US $0.00 / Kg/Bag	10g	99%min HPLC	10KGS	WUHAN FORTUNA CHEMICAL CO., LTD
2024-11-19	Pomalidomide 19171-19-8	US $52.00-101.00 / mg		98.8%	10g	TargetMol Chemicals Inc.
2024-11-19	Pomalidomide 19171-19-8	US $0.00 / g	1g	98% HPLC	100kg	shandong perfect biotechnology co.ltd

Pomalidomide
19171-19-8
US $0.00 / Kg/Bag
99%min HPLC
WUHAN FORTUNA CHEMICAL CO., LTD

Pomalidomide
19171-19-8
US $52.00-101.00 / mg
98.8%
TargetMol Chemicals Inc.

Pomalidomide
19171-19-8
US $0.00 / g
98% HPLC
shandong perfect biotechnology co.ltd

Pomalidomide Spectrum

Pomalidomide(19171-19-8)¹HNMR

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1of4

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