Pomalidomide

Base Information

• Chemical Name: Pomalidomide
• CAS No.: 19171-19-8
• Deprecated CAS: 443912-23-0,443919-33-3,443919-33-3
• Molecular Formula: C13H11N3O4
• Molecular Weight: 273.248
• Hs Code.: 29251900
• European Community (EC) Number: 805-902-5
• UNII: D2UX06XLB5
• DSSTox Substance ID: DTXSID40893458
• Nikkaji Number: J1.121.690K
• Wikipedia: Pomalidomide
• Wikidata: Q7227206
• NCI Thesaurus Code: C72560
• RXCUI: 1369713
• Pharos Ligand ID: 86HY57SRP723
• Metabolomics Workbench ID: 66067
• ChEMBL ID: CHEMBL43452
• Mol file: 19171-19-8.mol

Synonyms:actimid;CC 4047;CC-4047;CC4047;Imnovid;pomalidomide;Pomalyst

Chemical Property of Pomalidomide

Chemical Property:

• Vapor Pressure: 1.41E-13mmHg at 25°C
• Melting Point: 318.5 - 320.5°
• Refractive Index: 1.691
• Boiling Point: 582.933 °C at 760 mmHg
• PKA: 10.75±0.40(Predicted)
• Flash Point: 306.347 °C
• PSA: 109.57000
• Density: 1.57 g/cm³
• LogP: 0.51790
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥14mg/mL
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 273.07495584
• Heavy Atom Count: 20
• Complexity: 504

Purity/Quality:

99%MIN ^*data from raw suppliers

Pomalidomide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1CC(=O)NC(=O)C1N2C(=O)C3=C(C2=O)C(=CC=C3)N
• Recent ClinicalTrials: A Study to Evaluate CC-92480, Bortezomib and Dexamethasone (480Vd) Versus Pomalidomide, Bortezomib and Dexamethasone (PVd) in Participants With Relapsed or Refractory Multiple Myeloma (RRMM)
• Recent EU Clinical Trials: A Phase 1b Open-label Study to Evaluate the Safety and Tolerability of Intravenous Modakafusp Alfa as Part of Combination Therapy in Adult Patients With Multiple Myeloma
• Recent NIPH Clinical Trials: Multi-center, open-label, Phase 1b study in patients with relapsed/refractory multiple myeloma (RRMM)
• Description: Pomalidomide inhibits LPS-induced TNF-α release with IC50 of 13 nM in PBMCs. 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.
• 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. Pomalidomide is a second generation immunomodulator, TNF-α inhibitor, and thalidomide analog. An inhibitor of LPS-induced TNFαrelease. Pomalidomide inhibits LPS-induced TNF-α release with IC50 of 13 nM
• Clinical Use: Treatment of multiple myeloma
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: concentration increased by fluvoxamine.

Technology Process of Pomalidomide

There total 38 articles about Pomalidomide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.6%

ethyl 4-amino-1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate (340020-02-2) + (+/-)-α-aminoglutarimide (2353-44-8,673485-72-8) → pomalidomide (19171-19-8,202271-89-4)

Guidance literature:

With sodium acetate; In acetonitrile; for 4h; Reflux;

Reference yield: 96.0%

C14H15N3O5 → pomalidomide (19171-19-8,202271-89-4)

Guidance literature:

In acetonitrile; at 80 ℃; for 2.5h; Solvent; Temperature;

Reference yield: 95.6%

N-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)acetamide (444289-17-2) → pomalidomide (19171-19-8,202271-89-4)

Guidance literature:

With sodium hydroxide; In water; acetonitrile; at 80 ℃; for 8h; Reagent/catalyst; Temperature; Solvent;

upstream raw materials:

4-NT

3-nitrophthalic acid anhydride

Cbz-L-Gln

rac-α-aminoglutarimide hydrochloride

Downstream raw materials:

N-[2-(2,6-dioxo(3-piperidyl))-1,3-dioxoisoindolin-4-yl]benzamide

3-chloro-N-[2-(2,6-dioxo-piperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]-benzamide

Refernces

• 1、 Kim, Ga Yeong,Song, Chae Won,Yang, Yo-Sep,Lee, Na-Rae,Yoo, Hyung-Seok,Son, Seung Hwan,Lee, Soo Jin,Park, Jong Seon,Lee, Jong Kil,Inn, Kyung-Soo,Kim, Nam-Jung. "Chemical degradation of androgen receptor (Ar) using bicalutamide analog–thalidomide protacs". . . Retrieved 2021.
• 2、 Konstantinidou, Markella,Oun, Asmaa,Pathak, Pragya,Zhang, Bidong,Wang, Zefeng,ter Brake, Frans,Dolga, Amalia M.,Kortholt, Arjan,D?mling, Alexander. "The tale of proteolysis targeting chimeras (PROTACs) for Leucine-Rich Repeat Kinase 2 (LRRK2)". supporting information. p. 959 - 965. Retrieved 2020/12/30.