Lenalidomide

Identification

Summary

Lenalidomide is a thalidomide derivative used to treat multiple myeloma and anemia in low to intermediate risk myelodysplastic syndrome.

Brand Names
Revlimid
Generic Name
Lenalidomide
DrugBank Accession Number
DB00480
Background

Lenalidomide (previously referred to as CC-5013) is an immunomodulatory drug with potent antineoplastic, anti-angiogenic, and anti-inflammatory properties.4 It is a 4-amino-glutamyl analogue of thalidomide 3 and like thalidomide, lenalidomide exists as a racemic mixture of the active S(-) and R(+) forms.7 However, lenalidomide is much safer and potent than thalidomide, with fewer adverse effects and toxicities.2,3 Thalidomide and its analogues, including lenalidomide, are referred to as immunomodulatory imide drugs (also known as cereblon modulators), which are a class of immunomodulatory drugs that contain an imide group. Lenalidomide works through various mechanisms of actions that promote malignant cell death and enhance host immunity.7 Available as oral capsules, lenalidomide is approved by the FDA and EU for the treatment of multiple myeloma, myelodysplastic syndromes, mantle cell lymphoma, follicular lymphoma, and marginal zone lymphoma in selected patients.9 Due to severe teratogenicity, pregnancy must be excluded before the start of treatment and patients must enroll in the lenalidomide Risk Evaluation and Mitigation Strategy (REMS) program to ensure contraception adherence.7

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 259.2606
Monoisotopic: 259.095691297
Chemical Formula
C13H13N3O3
Synonyms
  • 1-oxo-2-(2,6-dioxopiperidin-3-yl)-4-aminoisoindoline
  • 3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione
  • Lenalidomida
  • Lenalidomide
External IDs
  • CC-5013
  • CDC 501
  • CDC-501
  • ENMD 0997
  • SYP-1512

Pharmacology

Indication

Lenalidomide is indicated for the treatment of adult patients with multiple myeloma (MM) in combination with dexamethasone. It is also indicated as maintenance therapy in multiple myeloma following autologous hematopoietic stem cell transplantation (auto-HSCT).

It is indicated for the treatment of adult patients with transfusion-dependent anemia due to low- or intermediate-1-risk myelodysplastic syndromes (MDS) associated with a deletion 5q cytogenetic abnormality with or without additional cytogenetic abnormalities.

Lenalidomide is indicated for the treatment of adult patients with mantle cell lymphoma (MCL) whose disease has relapsed or progressed after two prior therapies, one of which included bortezomib.

In combination with a rituximab product, lenalidomide is indicated for the treatment of adult patients with previously treated follicular lymphoma (FL) or previously treated marginal zone lymphoma (MZL).9

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatFollicular lymphoma (fl)Regimen in combination with: Rituximab (DB00073)••••••••••••••••••••••••••• ••••••••••••••
Treatment ofLight-chain amyloidosis••• •••••
Treatment ofMantle cell lymphoma••••••••••••••••••••••••• •••••• •••••••••• ••••••••• •• ••••• ••• ••••• •••••••• •••••••••••• •••••••••••••••
Used in combination to treatMarginal zone lymphoma (mzl)Regimen in combination with: Rituximab (DB00073)••••••••••••••••••••••••••• ••••••••••••••
Used in combination to treatMultiple myelomaRegimen in combination with: Dexamethasone (DB01234)•••••••••••••••••••••••••••••••• ••••••••••••• •••• •••• ••••••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

In hematological malignancies, the immune system is deregulated in the form of altered cytokine networks in the tumour microenvironment, defective T cell regulation of host-tumour immune interactions, and diminished NK cell activity.3 Lenalidomide is an immunomodulatory agent with antineoplastic, antiangiogenic, and anti-inflammatory properties.5 Lenalidomide exerts direct cytotoxicity by increasing apoptosis and inhibiting the proliferation of hematopoietic malignant cells.7 It delays tumour growth in nonclinical hematopoietic tumour models in vivo, including multiple myeloma.9 Lenalidomide also works to limit the invasion or metastasis of tumour cells and inhibits angiogenesis.7

Lenalidomide also mediates indirect antitumour effects via its immunomodulatory actions: it inhibits the production of pro-inflammatory cytokines, which are implicated in various hematologic malignancies. Lenalidomide enhances the host immunity by stimulating T cell proliferation and enhancing the activity of natural killer (NK) cells.1,6,7 Lenalidomide is about 100–1000 times more potent in stimulating T cell proliferation than thalidomide.3 In vitro, it enhances antibody-dependent cell-mediated cytotoxicity (ADCC), which is even more pronounced when used in combination with rituximab.9 Due to its anti-inflammatory properties, lenalidomide has been investigated in the context of inflammatory and autoimmune diseases, such as amyotrophic lateral sclerosis.8

Mechanism of action

Lenalidomide is a drug with multiple mechanisms of action. Lenalidomide exerts immunomodulating effects by altering cytokine production, regulating T cell co-stimulation, and enhancing the NK cell-mediated cytotoxicity.3 Lenalidomide directly inhibits the cullin ring E3 ubiquitin ligase complex: upon binding to cereblon, a substrate adaptor of the complex, lenalidomide modulates substrate specificity of the complex to recruit substrate proteins of the ligase, including Ikaros (IKZF1), Aiolos (IKZF3), and CK1α.9 These substrates are then tagged for ubiquitination and subsequent proteasomal degradation. IKZF1 and IKZF3 are B-cell transcription factors that are essential for B-cell differentiation and survival of malignant cells. IKZF3 also regulates the expression of interferon regulatory factor 4 (IRF4), which is a transcription factor that regulates the aberrant myeloma-specific gene. The immunomodulatory actions of lenalidomide can be partly explained by the degradation of IKZF3, since it is a repressor of the interleukin 2 gene (IL2): as lenalidomide decreases the level of IKZF3, the production of IL-2 increases, thereby increasing the proliferation of natural killer (NK), NKT cells, and CD4+ T cells.6 Lenalidomide inhibits the production of pro-inflammatory cytokines TNF-α, IL-1, IL-6, and IL-12, while elevating the production of anti-inflammatory cytokine IL-10.3 Lenalidomide acts as a T-cell co-stimulatory molecule that promotes CD3 T-cell proliferation and increases the production of IL-2 and IFN-γ in T lymphocytes, which enhances NK cell cytotoxicity and ADCC. It inhibits the expression and function of T-regulatory cells, which are often overabundant in some hematological malignancies.7

Lenalidomide directly exerts antitumour effects by inhibiting the proliferation and inducing apoptosis of tumour cells. Lenalidomide triggers the activation of pro-apoptotic caspase-8, enhances tumour cell sensitivity to FAS-induced apoptosis, and downregulates NF-κB, an anti-apoptotic protein.7 Independent of its immunomodulatory effects, lenalidomide mediates anti-angiogenic effects by inhibiting angiogenic growth factors released by tumour cells, such as vascular endothelial growth factor (VEGF), basic fibroblastic-growth factor (BFGF), and hepatocyte-growth factor. In vitro, lenalidomide inhibits cell adhesion molecules such as ICAM-1, LFA-1, β2 and β3 integrins, as well as gap-junction function, thereby preventing metastasis of malignant cells.7

TargetActionsOrganism
AProtein cereblon
inhibitor
Humans
ATumor necrosis factor ligand superfamily member 11
inhibitor
Humans
UCadherin-5
antagonist
Humans
UProstaglandin G/H synthase 2
negative modulator
Humans
Absorption

Following oral administration, lenalidomide is rapidly absorbed with high bioavailability.5 It has a Tmax ranging from 0.5 to six hours. Lenalidomide exhibits a linear pharmacokinetic profile, with its AUC and Cmax increasing proportionally with dose. Multiple dosing does not result in drug accumulation.9 In healthy male subjects, the Cmax was 413 ± 77 ng/ml and the AUCinfinity was 1319 ± 162 h x ng/ml.5

Volume of distribution

In healthy male subjects, the apparent volume of distribution was 75.8 ± 7.3 L.5

Protein binding

In vitro, about 30% of lenalidomide was bound to plasma proteins.9

Metabolism

Lenalidomide is not subject to extensive hepatic metabolism involving CYP enzymes and metabolism contributes to a very minor extent to the clearance of lenalidomide in humans. Lenalidomide undergoes hydrolysis in human plasma to form 5-hydroxy-lenalidomide and N-acetyl-lenalidomide.5 Unchanged lenalidomide is the predominant circulating drug form, with metabolites accounting for less than five percent of the parent drug levels in the circulation.9

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Route of elimination

Lenalidomide is eliminated predominantly via urinary excretion in the unchanged form. Following oral administration of 25 mg of radiolabeled lenalidomide in healthy subjects, about 90% of the dose (4.59% as metabolites) was eliminated in urine and 4% of the dose (1.83% as metabolites) was eliminated in feces within ten days post-dose. Approximately 85% of the dose was excreted as lenalidomide in the urine within 24 hours.9

Half-life

In healthy subjects, the mean half-life of lenalidomide is three hours in the clinically relevant dose range (5–50 mg).5 Half-life can range from three to five hours in patients with multiple myeloma, myelodysplastic syndromes, or mantle cell lymphoma.9

Clearance

The renal clearance of lenalidomide exceeds the glomerular filtration rate.9 In healthy male subjects, the oral clearance was 318 ± 41 mL/min.5

Adverse Effects
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Toxicity

The lowest lethal dose (LDLo) in rats is >2000 mg/kg following oral administration and >40 mg/kg following intravenous administration.10 The oral Lowest published toxic dose (TDLo) in humans is 9 mg/kg/4W (intermittent).11

There is limited clinical experience in managing lenalidomide overdose. In single-dose studies, healthy subjects have been exposed to doses up to 400 mg. In clinical trials, the dose-limiting toxicity was neutropenia and thrombocytopenia. Toxicities associated with lenalidomide, some leading to fatality, include embryo-fetal toxicity, neutropenia, thrombocytopenia, venous (deep vein thrombosis and pulmonary embolism) and arterial thromboembolic events (myocardial infarction and stroke), serious adverse cardiovascular reactions, second primary malignancies, hepatotoxicity, severe cutaneous reactions, tumour lysis syndrome, tumour flare reaction, hypothyroidism, and hyperthyroidism.9

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirLenalidomide may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe risk or severity of adverse effects can be increased when Lenalidomide is combined with Abatacept.
AbciximabThe risk or severity of bleeding can be increased when Abciximab is combined with Lenalidomide.
AceclofenacAceclofenac may decrease the excretion rate of Lenalidomide which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Lenalidomide which could result in a higher serum level.
Food Interactions
  • Take at the same time every day. Skip the missed dose if it has been more than 12 hours since your regular time.
  • Take with or without food. High-fat meals decrease absorption, but not to a clinically significant extent.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lenalidomide hydrochloride monohydrateNot AvailableNot AvailableNot applicable
International/Other Brands
Ladevina / Lenangio
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
LenalidomideCapsule20 mgOralNatco Pharma LimitedNot applicableNot applicableCanada flag
LenalidomideCapsule7.5 mgOralNatco Pharma LimitedNot applicableNot applicableCanada flag
LenalidomideCapsule15 mgOralNatco Pharma LimitedNot applicableNot applicableCanada flag
LenalidomideCapsule5 mgOralNatco Pharma LimitedNot applicableNot applicableCanada flag
LenalidomideCapsule10 mgOralNatco Pharma LimitedNot applicableNot applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-lenalidomideCapsule25 mgOralApotex Corporation2021-09-01Not applicableCanada flag
Apo-lenalidomideCapsule10 mgOralApotex Corporation2021-09-01Not applicableCanada flag
Apo-lenalidomideCapsule20 mgOralApotex Corporation2021-09-01Not applicableCanada flag
Apo-lenalidomideCapsule5 mgOralApotex Corporation2021-09-01Not applicableCanada flag
Apo-lenalidomideCapsule15 mgOralApotex Corporation2021-09-01Not applicableCanada flag

Categories

ATC Codes
L04AX04 — Lenalidomide
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Isoindoles and derivatives
Sub Class
Isoindolines
Direct Parent
Isoindolones
Alternative Parents
Alpha amino acids and derivatives / Isoindoles / Piperidinediones / Delta lactams / Benzenoids / Tertiary carboxylic acid amides / N-unsubstituted carboxylic acid imides / Dicarboximides / Azacyclic compounds / Primary amines
show 4 more
Substituents
Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid imide
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dicarboximide, aromatic amine, piperidones, isoindoles (CHEBI:63791)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
F0P408N6V4
CAS number
191732-72-6
InChI Key
GOTYRUGSSMKFNF-UHFFFAOYSA-N
InChI
InChI=1S/C13H13N3O3/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)
IUPAC Name
3-(4-amino-1-oxo-2,3-dihydro-1H-isoindol-2-yl)piperidine-2,6-dione
SMILES
NC1=CC=CC2=C1CN(C1CCC(=O)NC1=O)C2=O

References

Synthesis Reference

Surya Narayana Devarakonda, Sesha Reddy Yarraguntla, Vamsi Krishna Mudapaka, Rajasekhar Kadaboina, Veerender Murki, Amarendhar Manda, Venkata Rao Badisa, Naresh Vemula, Rama Seshagiri Rao Pulla, Venu Nalivela, "PREPARATION OF LENALIDOMIDE." U.S. Patent US20110021567, issued January 27, 2011.

US20110021567
General References
  1. Chang DH, Liu N, Klimek V, Hassoun H, Mazumder A, Nimer SD, Jagannath S, Dhodapkar MV: Enhancement of ligand-dependent activation of human natural killer T cells by lenalidomide: therapeutic implications. Blood. 2006 Jul 15;108(2):618-21. Epub 2006 Mar 28. [Article]
  2. Anderson KC: Lenalidomide and thalidomide: mechanisms of action--similarities and differences. Semin Hematol. 2005 Oct;42(4 Suppl 4):S3-8. [Article]
  3. Kotla V, Goel S, Nischal S, Heuck C, Vivek K, Das B, Verma A: Mechanism of action of lenalidomide in hematological malignancies. J Hematol Oncol. 2009 Aug 12;2:36. doi: 10.1186/1756-8722-2-36. [Article]
  4. Qiao SK, Guo XN, Ren JH, Ren HY: Efficacy and Safety of Lenalidomide in the Treatment of Multiple Myeloma: A Systematic Review and Meta-analysis of Randomized Controlled Trials. Chin Med J (Engl). 2015 May 5;128(9):1215-22. doi: 10.4103/0366-6999.156134. [Article]
  5. Chen N, Wen L, Lau H, Surapaneni S, Kumar G: Pharmacokinetics, metabolism and excretion of [(14)C]-lenalidomide following oral administration in healthy male subjects. Cancer Chemother Pharmacol. 2012 Mar;69(3):789-97. doi: 10.1007/s00280-011-1760-3. Epub 2011 Oct 29. [Article]
  6. Fink EC, Ebert BL: The novel mechanism of lenalidomide activity. Blood. 2015 Nov 19;126(21):2366-9. doi: 10.1182/blood-2015-07-567958. Epub 2015 Oct 5. [Article]
  7. Galustian C, Dalgleish A: Lenalidomide: a novel anticancer drug with multiple modalities. Expert Opin Pharmacother. 2009 Jan;10(1):125-33. doi: 10.1517/14656560802627903. [Article]
  8. Kiaei M, Petri S, Kipiani K, Gardian G, Choi DK, Chen J, Calingasan NY, Schafer P, Muller GW, Stewart C, Hensley K, Beal MF: Thalidomide and lenalidomide extend survival in a transgenic mouse model of amyotrophic lateral sclerosis. J Neurosci. 2006 Mar 1;26(9):2467-73. doi: 10.1523/JNEUROSCI.5253-05.2006. [Article]
  9. FDA Approved Products: Revlimid (Lenalidomide) oral capsules [Link]
  10. Celegene Corporation: Lenalidomide Safety Data Sheet [Link]
  11. Cayman Chemical: Lenalidomide Safety Data Sheet [Link]
  12. FDA Approved Products: REVLIMID (lenalidomide) capsules, for oral use 2022 [Link]
Human Metabolome Database
HMDB0014623
KEGG Drug
D04687
PubChem Compound
216326
PubChem Substance
46505725
ChemSpider
187515
BindingDB
65454
RxNav
342369
ChEBI
63791
ChEMBL
CHEMBL848
Therapeutic Targets Database
DAP001255
PharmGKB
PA162363968
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Lenalidomide
FDA label
Download (400 KB)
MSDS
Download (225 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentMultiple Myeloma (MM)2
4Active Not RecruitingTreatmentRelapsed/Refractory Multiple Myeloma (RRMM)1
4CompletedTreatmentCutaneous Lupus1
4CompletedTreatmentMultiple Myeloma (MM)1
4CompletedTreatmentRelapsed/Refractory Multiple Myeloma (RRMM)1

Pharmacoeconomics

Manufacturers
  • Celgene corp
  • Celgene Corporation
Packagers
  • Celgene
  • Norwich Pharmaceuticals Inc.
  • Penn Pharmaceutical Services Ltd.
Dosage Forms
FormRouteStrength
Capsule, coatedOral10 mg
CapsuleOral2.5 MG
Capsule, coatedOral15 mg
Capsule, coatedOral25 mg
Capsule, coatedOral5 mg
CapsuleOral7.5 mg
CapsuleOral10 mg/1
CapsuleOral15 mg/1
CapsuleOral2.5 mg/1
CapsuleOral20 mg
CapsuleOral20 mg/1
CapsuleOral25 mg/1
CapsuleOral5 mg/1
CapsuleOral5.000 mg
CapsuleOral10.0 mg
CapsuleOral15.0 mg
CapsuleOral25.0 mg
CapsuleOral5.0 mg
CapsuleOral10 mg
CapsuleOral15 mg
CapsuleOral25 mg
CapsuleOral
CapsuleOral5 MG
Prices
Unit descriptionCostUnit
Revlimid 25 mg capsule411.71USD capsule
Revlimid 15 mg capsule407.7USD capsule
Revlimid 10 mg capsule406.05USD capsule
Revlimid 5 mg capsule388.0USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2477301No2009-09-012023-04-13Canada flag
CA2342974No2005-08-162014-02-24Canada flag
US6045501No2000-04-042018-08-28US flag
US6315720No2001-11-132020-10-23US flag
US6561976No2003-05-132018-08-28US flag
US6561977No2003-05-132020-10-23US flag
US6755784No2004-06-292020-10-23US flag
US6908432No2005-06-212018-08-28US flag
US8204763No2012-06-192018-08-28US flag
US8315886No2012-11-202020-10-23US flag
US8626531No2014-01-072020-10-23US flag
US8589188No2013-11-192018-08-28US flag
US7468363No2008-12-232023-10-07US flag
US6281230No2001-08-282016-07-24US flag
US8530498No2013-09-102023-05-15US flag
US6555554No2003-04-292016-07-24US flag
US7189740No2007-03-132023-04-11US flag
US7968569No2011-06-282023-10-07US flag
US8404717No2013-03-262023-04-11US flag
US8648095No2014-02-112023-05-15US flag
US8741929No2014-06-032028-03-08US flag
US9101622No2015-08-112023-05-15US flag
US9101621No2015-08-112023-05-15US flag
US9056120No2015-06-162023-04-11US flag
US5635517No1997-06-032019-10-04US flag
US7119106No2006-10-102016-07-24US flag
US7465800No2008-12-162027-04-27US flag
US7855217No2010-12-212024-11-24US flag
US8288415No2012-10-162016-07-24US flag
US9393238No2016-07-192023-05-15US flag
US8492406No2013-07-232023-10-07US flag
US9155730No2015-10-132023-05-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubilitySoluble in organic solvent/water mixtures, and buffered aqueous solvents. Lenalidomide is more soluble in organic solvents and low pH solutions. Solubility was significantly lower in less acidic buffers, ranging from about 0.4 to 0.5 mg/mL.Not Available
logP-0.4Not Available
Predicted Properties
PropertyValueSource
logP-0.71Chemaxon
pKa (Strongest Acidic)11.61Chemaxon
pKa (Strongest Basic)2.31Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area92.5 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity68.3 m3·mol-1Chemaxon
Polarizability25.51 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.9372
Caco-2 permeable-0.5981
P-glycoprotein substrateSubstrate0.6845
P-glycoprotein inhibitor IInhibitor0.6012
P-glycoprotein inhibitor IINon-inhibitor0.8927
Renal organic cation transporterNon-inhibitor0.726
CYP450 2C9 substrateNon-substrate0.8861
CYP450 2D6 substrateNon-substrate0.7878
CYP450 3A4 substrateSubstrate0.5855
CYP450 1A2 substrateNon-inhibitor0.8746
CYP450 2C9 inhibitorNon-inhibitor0.8405
CYP450 2D6 inhibitorNon-inhibitor0.8806
CYP450 2C19 inhibitorNon-inhibitor0.78
CYP450 3A4 inhibitorNon-inhibitor0.7469
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.843
Ames testNon AMES toxic0.8268
CarcinogenicityNon-carcinogens0.9068
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity2.5145 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9803
hERG inhibition (predictor II)Non-inhibitor0.5098
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01si-4950000000-d56c036a1d29e5a9442f
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-1920000000-c10c48acd9b8123e3505
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-1920000000-c10c48acd9b8123e3505
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0290000000-cbaaed96c17a34ff1303
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0390000000-77b0a4d92e37271c4530
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qa-0930000000-c2a9cf544c87d9093bbc
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001s-1930000000-2bb8ee6d513e2dcae531
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-276ea26200dd2d5b13d6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6900000000-efe91deb6b0a3fcd3299
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-167.957836
predicted
DarkChem Lite v0.1.0
[M-H]-158.7324
predicted
DeepCCS 1.0 (2019)
[M+H]+168.307236
predicted
DarkChem Lite v0.1.0
[M+H]+161.09041
predicted
DeepCCS 1.0 (2019)
[M+Na]+168.261836
predicted
DarkChem Lite v0.1.0
[M+Na]+167.18356
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Substrate recognition component of a DCX (DDB1-CUL4-X-box) E3 protein ligase complex that mediates the ubiquitination and subsequent proteasomal degradation of target proteins, such as MEIS2. Norma...
Gene Name
CRBN
Uniprot ID
Q96SW2
Uniprot Name
Protein cereblon
Molecular Weight
50545.375 Da
References
  1. Zhu YX, Kortuem KM, Stewart AK: Molecular mechanism of action of immune-modulatory drugs thalidomide, lenalidomide and pomalidomide in multiple myeloma. Leuk Lymphoma. 2013 Apr;54(4):683-7. doi: 10.3109/10428194.2012.728597. Epub 2012 Sep 28. [Article]
  2. FDA Approved Products: Revlimid (Lenalidomide) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Tumor necrosis factor receptor superfamily binding
Specific Function
Cytokine that binds to TNFRSF11B/OPG and to TNFRSF11A/RANK. Osteoclast differentiation and activation factor. Augments the ability of dendritic cells to stimulate naive T-cell proliferation. May be...
Gene Name
TNFSF11
Uniprot ID
O14788
Uniprot Name
Tumor necrosis factor ligand superfamily member 11
Molecular Weight
35477.81 Da
References
  1. Akobeng AK, Stokkers PC: Thalidomide and thalidomide analogues for maintenance of remission in Crohn's disease. Cochrane Database Syst Rev. 2009 Apr 15;(2):CD007351. doi: 10.1002/14651858.CD007351.pub2. [Article]
  2. Melchert M, List A: The thalidomide saga. Int J Biochem Cell Biol. 2007;39(7-8):1489-99. Epub 2007 Jan 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Receptor binding
Specific Function
Cadherins are calcium-dependent cell adhesion proteins. They preferentially interact with themselves in a homophilic manner in connecting cells; cadherins may thus contribute to the sorting of hete...
Gene Name
CDH5
Uniprot ID
P33151
Uniprot Name
Cadherin-5
Molecular Weight
87527.715 Da
References
  1. Lu L, Payvandi F, Wu L, Zhang LH, Hariri RJ, Man HW, Chen RS, Muller GW, Hughes CC, Stirling DI, Schafer PH, Bartlett JB: The anti-cancer drug lenalidomide inhibits angiogenesis and metastasis via multiple inhibitory effects on endothelial cell function in normoxic and hypoxic conditions. Microvasc Res. 2009 Mar;77(2):78-86. doi: 10.1016/j.mvr.2008.08.003. Epub 2008 Sep 4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Negative modulator
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Payvandi F, Wu L, Haley M, Schafer PH, Zhang LH, Chen RS, Muller GW, Stirling DI: Immunomodulatory drugs inhibit expression of cyclooxygenase-2 from TNF-alpha, IL-1beta, and LPS-stimulated human PBMC in a partially IL-10-dependent manner. Cell Immunol. 2004 Aug;230(2):81-8. [Article]
  2. Zeldis JB, Schafer PH, Bennett BL, Mercurio F, Stirling DI: Potential new therapeutics for Waldenstrom's macroglobulinemia. Semin Oncol. 2003 Apr;30(2):275-81. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Chen N, Weiss D, Reyes J, Liu L, Kasserra C, Wang X, Zhou S, Kumar G, Weiss L, Palmisano M: No clinically significant drug interactions between lenalidomide and Pglycoprotein substrates and inhibitors: results from controlled phase I studies in healthy volunteers. Cancer Chemother Pharmacol. 2014 May;73(5):1031-9. doi: 10.1007/s00280-014-2438-4. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2024 11:06