Lenalidomide hydrochloride

Name: Lenalidomide hydrochloride
Brand: BOC Sciences
Rating: 5 (1 reviews)

CAS No.: 1243329-97-6

Cat No.: BP-200075

Purity: >98% 4.5

Lenalidomide hydrochloride is a potent derivative of thalidomide, commonly used as an E3 ligase ligand for cereblon (CRBN) in PROTAC drug discovery. As a key building block in targeted protein degradation research, lenalidomide hydrochloride enables the design of PROTACs that recruit the CRBN E3 ubiquitin ligase complex, facilitating the selective ubiquitination and proteasomal degradation of disease-relevant proteins. It is classified under "E3 Ligase Ligand" and is instrumental in developing next-generation therapeutics for oncology, immunology, and neurodegenerative disorders. This compound offers pharmaceutical researchers a robust and reliable foundation for assembling innovative degrader molecules.

Structure of 1243329-97-6

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Category

Ligand for E3 Ligase

Molecular Formula

C13H14ClN3O3

Molecular Weight

295.72

Related CAS

<a href="/product/lenalidomide-hemihydrate-cas-847871-99-2-463648.html">847871-99-2</a> (hydrochloride)

* For research and manufacturing use only. Not for human or clinical use.

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Capabilities & Facilities

Comprehensive PROTAC Platform
Scientific Expertise & Technical Support
Custom Synthesis & Design Service
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Purity

>98%

Solubility

≥ 72.2 mg/mL in DMSO, ≥ 1.83 mg/mL in EtOH

Storage

Store at -20°C

Synonyms

Revlimid hydrochloride; CC-5013 hydrochloride; CC5013 hydrochloride; CC 5013 hydrochloride

InChI Key

RYWZLJSDFZVVTD-UHFFFAOYSA-N

InChI

InChI=1S/C13H13N3O3.ClH/c14-9-3-1-2-7-8(9)6-16(13(7)19)10-4-5-11(17)15-12(10)18;/h1-3,10H,4-6,14H2,(H,15,17,18);1H

SMILES

C1CC(=O)NC(=O)C1N2CC3=C(C2=O)C=CC=C3N.Cl

Background Introduction

Lenalidomide hydrochloride is the hydrochloride salt form of lenalidomide, a potent immunomodulatory imide drug (IMiD) and a widely used E3 ligase ligand targeting Cereblon (CRBN). As an FDA-approved therapeutic agent for multiple myeloma and other hematological malignancies, lenalidomide is also an integral building block in the design of PROTACs (Proteolysis Targeting Chimeras) that harness the cellular ubiquitin-proteasome system for targeted protein degradation. Its high affinity for CRBN and well-characterized pharmacological profile have established lenalidomide hydrochloride as a gold standard for both therapeutic applications and chemical biology research.

Mechanism

Lenalidomide hydrochloride functions by binding with high specificity to the CRBN substrate receptor within the CUL4-CRBN E3 ubiquitin ligase complex. This binding facilitates the recruitment of neosubstrate proteins, such as IKZF1 and IKZF3, leading to their ubiquitination and subsequent degradation by the proteasome. In PROTAC technology, lenalidomide hydrochloride serves as the E3 ligase-recruiting moiety, enabling the formation of bifunctional molecules that bring CRBN in proximity to a target protein, thereby inducing targeted degradation through the ubiquitin-proteasome pathway.

Applications

Lenalidomide hydrochloride is extensively leveraged in the design and synthesis of CRBN-based PROTAC molecules, offering researchers a reliable and effective means to recruit E3 ubiquitin ligase activity for targeted protein degradation. Its applications span:

• Development of novel CRBN-recruiting PROTACs for drug discovery and target validation
• Structure-activity relationship (SAR) studies to optimize degrader efficacy and selectivity
• Exploration of neosubstrate biology and molecular glues for selective protein degradation
• Custom synthesis projects requiring a proven and pharmaceutically-relevant E3 ligase ligand

Thanks to its robust chemical stability and established safety profile, lenalidomide hydrochloride remains a cornerstone in the fields of chemical biology, medicinal chemistry, and next-generation therapeutic research.

• High-purity compound verified by HPLC, NMR, and LC-MS
• Consistent batch-to-batch reproducibility with complete QC documentation
• Supplied with COA, MSDS, and analytical data for traceability
• Reliable global shipping with stability-guaranteed packaging
• Dedicated technical support and optional custom synthesis service
• Demonstrates strong binding affinity to CRBN, VHL, or other E3 ligases
• Enables stable E3 ligase recruitment for targeted protein degradation
• High affinity cereblon ligand enables efficient E3 ligase recruitment for targeted protein degradation.
• Pharmaceutical-grade compound suitable for use in PROTAC design, drug discovery, and chemical biology research.

1.A phase I study of bendamustine, lenalidomide and rituximab in relapsed and refractory lymphomas.

Cheson BD1, Crawford J. Br J Haematol. 2015 May;169(4):528-33. doi: 10.1111/bjh.13321. Epub 2015 Mar 7.

Many patients with non-Hodgkin (NHL) or Hodgkin lymphoma (HL) relapse or are refractory to initial therapy and require additional options. Bendamustine (B), lenalidomide (L) and rituximab (R) each have activity in this setting. This study was performed to determine the safety of BLR and its optimal phase II dose. Patients with NHL or HL failing standard therapies received B (90 mg/m(2) days 1, 2 every 28 days), and L (escalating from 5 mg 21/28 days) for six cycles, followed by 6 months of L. At the highest dose R 375 mg/m(2) on day one of each cycle was added for patients with B-NHL. Histologies included diffuse large B-cell lymphoma (DLBCL, 11), marginal zone lymphoma (3), HL (2), and one each of transformed follicular lymphoma, Sézary syndrome, Waldenström macroglobulinaemia and mantle cell lymphoma. Neutropenia was the most common grade 3 and 4 toxicity, but no maximum tolerated dose was identified. Of 20 patients, seven responded (35%), including four complete remissions, with five unmaintained responses from 28+ to 37+ months, including 2 DLBCL.

2.Ezatiostat hydrochloride for the treatment of myelodysplastic syndromes.

Mahadevan D1, Sutton GR. Expert Opin Investig Drugs. 2015 May;24(5):725-33. doi: 10.1517/13543784.2015.1021003. Epub 2015 Feb 27.

INTRODUCTION: Myelodysplastic syndromes (MDSs) are associated with significant morbidity due to ineffective hematopoiesis. Given the limited number of drugs approved by the FDA, there is a need for new therapeutic options. Ezatiostat is a novel agent targeting oxidative stress via inhibition of glutathione S-transferase 1.

3.Bendamustine in combination with thalidomide and dexamethasone is a viable salvage option in myeloma relapsed and/or refractory to bortezomib and lenalidomide.

Lau IJ1, Smith D, Aitchison R, Blesing N, Roberts P, Peniket A, Yong K, Rabin N, Ramasamy K. Ann Hematol. 2015 Apr;94(4):643-9. doi: 10.1007/s00277-014-2238-2. Epub 2014 Oct 28.

Treatment options are limited in myeloma relapsed or refractory to both bortezomib and lenalidomide (double-relapsed/refractory multiple myeloma; DRMM). Bendamustine is an antitumour agent that has efficacy in relapsed myeloma. We retrospectively analysed data from 30 DRMM patients who received a combination of bendamustine, thalidomide and dexamethasone (BTD) in 28-day treatment cycles. Bendamustine was administered with a cumulative dose of up to 200 mg/m(2). Thalidomide (50-150 mg) was given daily as tolerated, and dexamethasone was given at an equivalent dose of up to 160 mg per cycle. A median of 5 (2-9) treatment cycles were administered per patient. Twenty-six patients (87 %) achieved stable disease or better. At a median follow-up time of 12.1 (2.3-21.5) months, median (95 % CI) progression-free survival and overall survival were 4.0 (2.6-5.3) months and 7.2 (5.2-9.2) months, respectively. The most common grade 3-4 adverse events were haematological: anaemia (n = 8, 34.

4.A comprehensive review of lenalidomide therapy for B-cell non-Hodgkin lymphoma.

Witzig TE1, Nowakowski GS2, Habermann TM2, Goy A3, Hernandez-Ilizaliturri FJ4, Chiappella A5, Vitolo U5, Fowler N6, Czuczman MS4. Ann Oncol. 2015 Aug;26(8):1667-77. doi: 10.1093/annonc/mdv102. Epub 2015 Feb 23.

Lenalidomide is an oral non-chemotherapy immunomodulator with direct and indirect effects on non-Hodgkin lymphoma (NHL) cells and with single-agent activity in relapsed/refractory aggressive and indolent B-cell NHL, including mantle cell lymphoma (MCL), diffuse large B-cell lymphoma, and follicular lymphoma. Based on the pivotal phase II MCL-001 trial of lenalidomide in heavily pretreated patients with relapsed/refractory MCL, lenalidomide was approved by the US Food and Drug Administration for the treatment of relapsed/refractory MCL after failure of two prior therapies, one of which includes bortezomib, at a recommended starting dose of 25 mg on days 1-21 of each 28-day cycle. Lenalidomide enhanced the survival benefit in combination with rituximab in preclinical models, prompting clinical evaluation of the lenalidomide-rituximab (R2) combination. In phase II trials, lenalidomide 20 mg on days 1-21 in combination with different standard-dose rituximab schedules exhibited promising activity in both first-line and relapsed/refractory disease across multiple B-cell NHL subtypes.

ConcentrationVolumeMass	1 mg	5 mg	10 mg
1 mM	3.3816 mL	16.9079 mL	33.8158 mL
5 mM	0.6763 mL	3.3816 mL	6.7632 mL
10 mM	0.3382 mL	1.6908 mL	3.3816 mL

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂