1243329-97-6

Basic information

• Product Name: CC 5013 hydrochloride
• Synonyms: CC 5013 hydrochloride;CC5013 hydrochloride;CC-5013 hydrochloride;LenalidoMide (hydrochloride);RevliMid hydrochloride;Lenalidomide HCl
• CAS NO: 1243329-97-6
• Molecular Formula: C₁₃H₁₃N₃O₃*ClH
• Molecular Weight: 295.72156
• Mol File: 1243329-97-6.mol

Chemical Properties

• Appearance: /
• Solubility: insoluble in H2O; ≥1.83 mg/mL in EtOH; ≥72.2 mg/mL in DMSO
• CAS DataBase Reference: CC 5013 hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: CC 5013 hydrochloride(1243329-97-6)
• EPA Substance Registry System: CC 5013 hydrochloride(1243329-97-6)

Safety Data

• Hazardous Substances Data: 1243329-97-6(Hazardous Substances Data)

Usage

Biological Activity

lenalidomideis a derivative of thalidomide introduced in 2004. lenalidomide (revlimid, cc-5013) is a tnf-α secretion inhibitor with ic50 of 13 nm.

in vitro

lenalidomide strongly induces il-2 and sil-2r production. lenalidomide-induced tyrosine phosphorylation of cd28 on t cells is followed by a down-stream activation of nf-κb [2]. lenalidomide and pomalidomide inhibits autoubiquitination of crbn in hek293 t cells expressing thalidomide-binding competent wild-type crbn, but not thalidomide-binding defective crbn (yw/aa). overexpression of crbn wild-type protein, but not crbn (yw/aa) mutant protein, in kms12 myeloma cells, amplifies pomalidomide-mediated reductions in c-myc and irf4 expression and increases in p21(waf-1) expression. long-term selection for lenalidomide resistance in h929 myeloma cell lines is accompanied by a reduction in crbn, while in df15r myeloma cells resistant to both pomalidomide and lenalidomide, crbn protein is undetectable [3].

in vivo

pharmacokinetic studies evaluated doses of 0.5, 1.5, 5, and 10 mg/kg iv and 0.5 and 10 mg/kg doses for ip and oral routes. liquid chromatography-tandem mass spectrometry was used to quantify lenalidomide in plasma, brain, lung, liver, heart, kidney, spleen, and muscle [4]. treatment with either thalidomide or lenalidomide attenuated weight loss, enhanced motor performance, decreased motor neuron cell death, and significantly increased the life span in g93a transgenic mice [5].

IC 50

value: 13 nm [1] lenalidomideis a derivative of thalidomide introduced in 2004. lenalidomide (revlimid, cc-5013) is a tnf-α secretion inhibitor with ic50 of 13 nm. in vitro: lenalidomide strongly induces il-2 and sil-2r production. lenalidomide-induced tyrosine phosphorylation of cd28 on t cells is followed by a down-stream activation of nf-κb [2]. lenalidomide and pomalidomide inhibits autoubiquitination of crbn in hek293 t cells expressing thalidomide-binding competent wild-type crbn, but not thalidomide-binding defective crbn (yw/aa). overexpression of crbn wild-type protein, but not crbn (yw/aa) mutant protein, in kms12 myeloma cells, amplifies pomalidomide-mediated reductions in c-myc and irf4 expression and increases in p21(waf-1) expression. long-term selection for lenalidomide resistance in h929 myeloma cell lines is accompanied by a reduction in crbn, while in df15r myeloma cells resistant to both pomalidomide and lenalidomide, crbn protein is undetectable [3]. in vivo: pharmacokinetic studies evaluated doses of 0.5, 1.5, 5, and 10 mg/kg iv and 0.5 and 10 mg/kg doses for ip and oral routes. liquid chromatography-tandem mass spectrometry was used to quantify lenalidomide in plasma, brain, lung, liver, heart, kidney, spleen, and muscle [4]. treatment with either thalidomide or lenalidomide attenuated weight loss, enhanced motor performance, decreased motor neuron cell death, and significantly increased the life span in g93a transgenic mice [5]. toxicity: international staging system iii received a combination therapy of lenalidomide (15 mg, day 1 - 21) with dexamethasone (40 mg, day 1, 8, 15, 22). after 4 days on chemotherapy, he experienced worsened dyspnea and was urgently hospitalized because of acute respiratory failure [6].

Upstream product

• 879126-98-4 Lenalidomide 
• 827026-45-9 3-(4-nitro-1-oxoisoindolin-2-yl)piperidine-2,6-dione 
• 24666-56-6 rac-α-aminoglutarimide hydrochloride 
• 59382-59-1 2-methyl-3-nitro-benzoic acid methyl ester 
• 98475-07-1 2-bromomethyl-3-nitro-benzoic acid methyl ester 
• 6398-06-7 N-benzyloxycarbonyl-L-isoglutamine 
• 77658-84-5 N-(2,6-dioxopiperidin-3-yl)-2-phenylacetamide 

Downstream Products

• 879126-98-4 Lenalidomide 

Relevant articles and documents

ACID ADDITION SALTS OF LENALIDOMIDE

The invention relates to acid addition salts of lenalidomide as well as to desirable polymorphic forms of lenalidomide hydrogen sulfate. Furthermore, the invention provides a process for producing acid addition salts of lenalidomide, which optionally can comprise a further step producing lenalidomide in form of the free base.

SALTS OF 3-(4-AMINO-1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL)PIPERIDINE-2,6-DIONE AND DERIVATIVES THEREOF, OR POLYMORPHS OF SALTS, PROCESS FOR PREPARING SAME AND USE THEREOF

The present invention provides a pharmaceutically acceptable strong acid salt of 3-(4-amino-1-oxo-1,3-dihydro-isoindol-2-yl)piperidine-2,6-dione, a solvate thereof, a process for preparing the same and use in the preparation of a medicament for treating d