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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyLenalidomide
Identification
- Name
- Lenalidomide
- Accession Number
- DB00480 (APRD01303)
- Type
- Small Molecule
- Groups
- Approved
- Description
Lenalidomide (initially known as CC-5013 and marketed as Revlimid® by Celgene) is a derivative of thalidomide introduced in 2004. It was initially intended as a treatment for multiple myeloma, for which thalidomide is an accepted therapeutic modality, but has also shown efficacy in the hematological disorders known as the myelodysplastic syndromes. [Wikipedia] FDA approved on December 27, 2005.
- Structure
Structure for DB00480 (Lenalidomide)
- Synonyms
- 1-oxo-2-(2,6-Dioxopiperidin-3-yl)-4-aminoisoindoline
- 3-(4-Amino-1-oxoisoindolin-2-yl)piperidine-2,6-dione
- CC-5013
- CDC 501
- IMid-1
- IMiD3
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Revlimid Capsule 20 mg Oral Celgene Europe Limited 2007-06-14 Not applicable EU 
Revlimid Capsule 20 mg/1 Oral Celgene 2013-06-06 Not applicable US 
Revlimid Capsule 5 mg Oral Celgene Europe Limited 2007-06-14 Not applicable EU Revlimid Capsule 25 mg Oral Celgene 2008-10-10 Not applicable Canada 
Revlimid Capsule 7.5 mg Oral Celgene Europe Limited 2007-06-14 Not applicable EU Revlimid Capsule 15 mg Oral Celgene Europe Limited 2007-06-14 Not applicable EU Revlimid Capsule 5 mg/1 Oral Celgene 2005-12-27 Not applicable US Revlimid Capsule 5 mg Oral Celgene 2008-02-19 Not applicable Canada Revlimid Capsule 2.5 mg Oral Celgene 2016-12-20 Not applicable Canada Revlimid Capsule 5 mg Oral Celgene Europe Limited 2007-06-14 Not applicable EU - International/Other Brands
- Ladevina / Lenangio / Revlimid
- Categories
- Acids, Carbocyclic
- Angiogenesis Inhibitors
- Angiogenesis Modulating Agents
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Growth Inhibitors
- Growth Substances
- Imides
- Immunologic Factors
- Immunosuppressive Agents
- Isoindoles
- Myelosuppressive Agents
- P-glycoprotein/ABCB1 Substrates
- Phthalic Acids
- Phthalimides
- Piperidines
- Piperidones
- Thalidomide Analog
- UNII
- F0P408N6V4
- CAS number
- 191732-72-6
- Weight
- Average: 259.2606
Monoisotopic: 259.095691297 - Chemical Formula
- C13H13N3O3
- 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
Pharmacology
- Indication
Lenalidomide is indicated for the treatment of multiple myeloma in combination with dexamethasone. It is also indicated for the treatment of patients with transfusion-dependent anemia due to low- or intermediate- risk myelodysplastic syndromes (MDS) associated with a deletion 5q cytogenetic abnormality with or without additional cytogenetic abnormalities.
- Associated Conditions
- Pharmacodynamics
Lenalidomide, a thalidomide analogue, is an immunomodulatory agent possessing immunomodulatory and antiangiogenic properties. Lenalidomide inhibits the secretion of pro-inflammatory cytokines and increases the secretion of anti-inflammatory cytokines from peripheral blood mononuclear cells. Lenalidomide inhibits cell proliferation with varying effectiveness (IC50s) in some but not all cell lines. Lenalidomide is effective in inhibiting growth of Namalwa cells (a human B cell lymphoma cell line with a deletion of one chromosome 5) but is much less effective in inhibiting growth of KG-1 cells (human myeloblastic cell line, also with a deletion of one chromosome 5) and other cell lines without chromosome 5 deletions. Lenalidomide does not prolong the QTc interval.
- Mechanism of action
The mechanism of action of lenalidomide remains to be fully characterized, however it has been demonstrated that lenalidomide inhibits the expression of cyclooxygenase-2 (COX-2), but not COX-1, in vitro. In vivo it induces tumor cell apoptosis directly and indirectly by inhibition of bone marrow stromal cell support, by anti-angiogenic and anti-osteoclastogenic effects, and by immunomodulatory activity
Target Actions Organism AProtein cereblon inhibitorHuman ATumor necrosis factor ligand superfamily member 11 inhibitorHuman UCadherin-5 antagonistHuman UProstaglandin G/H synthase 2 negative modulatorHuman - Absorption
Rapidly absorbed following oral administration, with maximum plasma concentrations occurring between 0.625 and 1.5 hours post-dose. Co-administration with food does not alter the extent of absorption (AUC) but does reduce the maximal plasma concentration (Cmax) by 36%. The pharmacokinetic disposition of lenalidomide is linear. Accumulation does not occur following multiple doses.
- Volume of distribution
- Not Available
- Protein binding
30% protein bound.
- Metabolism
Lenalidomide undergoes limited metabolism. Unchanged lenalidomide is the predominant circulating component in humans. Two identified metabolites are hydroxy-lenalidomide and N-acetyl-lenalidomide; each constitutes less than 5% of parent levels in circulation. The cytochrome P450 enzyme system is not involved with the metabolism of lenalidomide.
- Route of elimination
Elimination is primarily renal. When a single oral dose of 25 mg is given healthy subjects, 90% and 4% of the dose is eliminated in urine and feces, respectively. Hydroxy-lenalidomide and N-acetyl-lenalidomide represent 4.59% and 1.83% of the excreted dose, respectively.
- Half life
Healthy subjects = 3 hours; Multiple myeloma or MDS patients = 3 - 5 hours.
- Clearance
The renal clearance of lenalidomide exceeds the glomerular filtration rate.
- Toxicity
The most frequently reported adverse events were related to blood and lymphatic system disorders, skin and subcutaneous tissue disorders, gastrointestinal disorders, and general disorders and administrative site conditions.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Lenalidomide. Approved Acetyldigoxin Acetyldigoxin may decrease the cardiotoxic activities of Lenalidomide. Experimental Ancestim The risk or severity of cytotoxicity can be increased when Ancestim is combined with Lenalidomide. Approved, Investigational, Withdrawn Anthrax immune globulin human The risk or severity of adverse effects can be increased when Lenalidomide is combined with Anthrax immune globulin human. Approved Apalutamide The serum concentration of Lenalidomide can be decreased when it is combined with Apalutamide. Approved, Investigational Bacillus calmette-guerin substrain connaught live antigen The risk or severity of adverse effects can be increased when Lenalidomide is combined with Bacillus calmette-guerin substrain connaught live antigen. Approved, Investigational Bacillus calmette-guerin substrain tice live antigen The risk or severity of adverse effects can be increased when Lenalidomide is combined with Bacillus calmette-guerin substrain tice live antigen. Approved Bazedoxifene Bazedoxifene may increase the thrombogenic activities of Lenalidomide. Approved, Investigational BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Lenalidomide. Investigational Bevacizumab Bevacizumab may increase the cardiotoxic activities of Lenalidomide. Approved, Investigational Cabazitaxel The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Lenalidomide. Approved Chlorotrianisene Chlorotrianisene may increase the thrombogenic activities of Lenalidomide. Investigational, Withdrawn Clostridium tetani toxoid antigen (formaldehyde inactivated) The risk or severity of adverse effects can be increased when Lenalidomide is combined with Clostridium tetani toxoid antigen (formaldehyde inactivated). Approved Clozapine The risk or severity of adverse effects can be increased when Lenalidomide is combined with Clozapine. Approved Conjugated estrogens Conjugated estrogens may increase the thrombogenic activities of Lenalidomide. Approved Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated) The risk or severity of adverse effects can be increased when Lenalidomide is combined with Corynebacterium diphtheriae toxoid antigen (formaldehyde inactivated). Approved Cyclophosphamide Cyclophosphamide may increase the cardiotoxic activities of Lenalidomide. Approved, Investigational Cymarin Cymarin may decrease the cardiotoxic activities of Lenalidomide. Experimental Daidzein Daidzein may increase the thrombogenic activities of Lenalidomide. Experimental Darbepoetin alfa Darbepoetin alfa may increase the thrombogenic activities of Lenalidomide. Approved, Investigational Denosumab The risk or severity of adverse effects can be increased when Denosumab is combined with Lenalidomide. Approved Deslanoside Deslanoside may decrease the cardiotoxic activities of Lenalidomide. Approved Dexamethasone Dexamethasone may increase the thrombogenic activities of Lenalidomide. Approved, Investigational, Vet Approved Dienestrol Dienestrol may increase the thrombogenic activities of Lenalidomide. Approved, Investigational Diethylstilbestrol Diethylstilbestrol may increase the thrombogenic activities of Lenalidomide. Approved, Investigational Digitoxin Digitoxin may decrease the cardiotoxic activities of Lenalidomide. Approved, Investigational Digoxin The serum concentration of Digoxin can be increased when it is combined with Lenalidomide. Approved Digoxin Immune Fab (Ovine) Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Lenalidomide. Approved Docetaxel The risk or severity of adverse effects can be increased when Docetaxel is combined with Lenalidomide. Approved, Investigational Epimestrol Epimestrol may increase the thrombogenic activities of Lenalidomide. Experimental Equol Equol may increase the thrombogenic activities of Lenalidomide. Investigational Erythropoietin Erythropoietin may increase the thrombogenic activities of Lenalidomide. Approved Estradiol Estradiol may increase the thrombogenic activities of Lenalidomide. Approved, Investigational, Vet Approved Estradiol acetate Estradiol acetate may increase the thrombogenic activities of Lenalidomide. Approved, Investigational, Vet Approved Estradiol cypionate Estradiol cypionate may increase the thrombogenic activities of Lenalidomide. Approved, Investigational, Vet Approved Estradiol valerate Estradiol valerate may increase the thrombogenic activities of Lenalidomide. Approved, Investigational, Vet Approved Estriol Estriol may increase the thrombogenic activities of Lenalidomide. Approved, Investigational, Vet Approved Estrogens, esterified Estrogens, esterified may increase the thrombogenic activities of Lenalidomide. Approved Estrone Estrone may increase the thrombogenic activities of Lenalidomide. Approved Ethinyl Estradiol Ethinyl Estradiol may increase the thrombogenic activities of Lenalidomide. Approved Fingolimod Lenalidomide may increase the immunosuppressive activities of Fingolimod. Approved, Investigational G17DT The risk or severity of adverse effects can be increased when Lenalidomide is combined with G17DT. Investigational Genistein Genistein may increase the thrombogenic activities of Lenalidomide. Investigational GI-5005 The risk or severity of adverse effects can be increased when Lenalidomide is combined with GI-5005. Investigational Gitoformate Gitoformate may decrease the cardiotoxic activities of Lenalidomide. Experimental Hepatitis A Vaccine The risk or severity of adverse effects can be increased when Lenalidomide is combined with Hepatitis A Vaccine. Approved Hepatitis B Vaccine (Recombinant) The risk or severity of adverse effects can be increased when Lenalidomide is combined with Hepatitis B Vaccine (Recombinant). Approved, Withdrawn Hexestrol Hexestrol may increase the thrombogenic activities of Lenalidomide. Withdrawn Human rabies virus immune globulin The risk or severity of adverse effects can be increased when Lenalidomide is combined with Human rabies virus immune globulin. Approved INGN 201 The risk or severity of adverse effects can be increased when Lenalidomide is combined with INGN 201. Investigational INGN 225 The risk or severity of adverse effects can be increased when Lenalidomide is combined with INGN 225. Investigational Isavuconazole The serum concentration of Lenalidomide can be increased when it is combined with Isavuconazole. Approved, Investigational Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated) The risk or severity of adverse effects can be increased when Lenalidomide is combined with Japanese encephalitis virus strain sa 14-14-2 antigen (formaldehyde inactivated). Approved Lanatoside C Lanatoside C may decrease the cardiotoxic activities of Lenalidomide. Experimental Leflunomide The risk or severity of adverse effects can be increased when Lenalidomide is combined with Leflunomide. Approved, Investigational Lipegfilgrastim Lenalidomide may increase the myelosuppressive activities of Lipegfilgrastim. Approved, Investigational Lumacaftor The serum concentration of Lenalidomide can be decreased when it is combined with Lumacaftor. Approved Mestranol Mestranol may increase the thrombogenic activities of Lenalidomide. Approved Metamizole The risk or severity of myelosuppression can be increased when Metamizole is combined with Lenalidomide. Approved, Investigational, Withdrawn Methallenestril Methallenestril may increase the thrombogenic activities of Lenalidomide. Experimental Methoxy polyethylene glycol-epoetin beta Methoxy polyethylene glycol-epoetin beta may increase the thrombogenic activities of Lenalidomide. Approved Metildigoxin Metildigoxin may decrease the cardiotoxic activities of Lenalidomide. Experimental Moxestrol Moxestrol may increase the thrombogenic activities of Lenalidomide. Experimental Natalizumab The risk or severity of adverse effects can be increased when Lenalidomide is combined with Natalizumab. Approved, Investigational Ocrelizumab Ocrelizumab may increase the immunosuppressive activities of Lenalidomide. Approved, Investigational Oleandrin Oleandrin may decrease the cardiotoxic activities of Lenalidomide. Experimental, Investigational Ouabain Ouabain may decrease the cardiotoxic activities of Lenalidomide. Approved Paclitaxel The risk or severity of adverse effects can be increased when Paclitaxel is combined with Lenalidomide. Approved, Vet Approved Peruvoside Peruvoside may decrease the cardiotoxic activities of Lenalidomide. Experimental Pimecrolimus The risk or severity of adverse effects can be increased when Pimecrolimus is combined with Lenalidomide. Approved, Investigational Pitolisant The serum concentration of Lenalidomide can be decreased when it is combined with Pitolisant. Approved, Investigational Polyestradiol phosphate Polyestradiol phosphate may increase the thrombogenic activities of Lenalidomide. Approved Promestriene Promestriene may increase the thrombogenic activities of Lenalidomide. Investigational Proscillaridin Proscillaridin may decrease the cardiotoxic activities of Lenalidomide. Experimental Quinestrol Quinestrol may increase the thrombogenic activities of Lenalidomide. Approved Rabies virus inactivated antigen, A The risk or severity of adverse effects can be increased when Lenalidomide is combined with Rabies virus inactivated antigen, A. Approved, Investigational Rabies virus inactivated antigen, A The therapeutic efficacy of Rabies virus inactivated antigen, A can be decreased when used in combination with Lenalidomide. Approved, Investigational Ranolazine The serum concentration of Lenalidomide can be increased when it is combined with Ranolazine. Approved, Investigational Rindopepimut The risk or severity of adverse effects can be increased when Lenalidomide is combined with Rindopepimut. Investigational Roflumilast Roflumilast may increase the immunosuppressive activities of Lenalidomide. Approved Rotavirus Vaccine The risk or severity of adverse effects can be increased when Lenalidomide is combined with Rotavirus Vaccine. Approved Rubella virus vaccine The risk or severity of adverse effects can be increased when Lenalidomide is combined with Rubella virus vaccine. Approved, Investigational Salmonella typhi ty2 vi polysaccharide antigen The risk or severity of adverse effects can be increased when Lenalidomide is combined with Salmonella typhi ty2 vi polysaccharide antigen. Approved Salmonella typhi ty21a live antigen The risk or severity of adverse effects can be increased when Lenalidomide is combined with Salmonella typhi ty21a live antigen. Approved Secoisolariciresinol Secoisolariciresinol may increase the thrombogenic activities of Lenalidomide. Investigational Sipuleucel-T The therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Lenalidomide. Approved, Investigational SRP 299 The risk or severity of adverse effects can be increased when Lenalidomide is combined with SRP 299. Investigational Synthetic Conjugated Estrogens, A Synthetic Conjugated Estrogens, A may increase the thrombogenic activities of Lenalidomide. Approved Synthetic Conjugated Estrogens, B Synthetic Conjugated Estrogens, B may increase the thrombogenic activities of Lenalidomide. Approved Tacrolimus Tacrolimus may increase the immunosuppressive activities of Lenalidomide. Approved, Investigational Tecemotide The risk or severity of adverse effects can be increased when Lenalidomide is combined with Tecemotide. Investigational TG4010 The risk or severity of adverse effects can be increased when Lenalidomide is combined with TG4010. Investigational Tibolone Tibolone may increase the thrombogenic activities of Lenalidomide. Approved, Investigational Tofacitinib Lenalidomide may increase the immunosuppressive activities of Tofacitinib. Approved, Investigational Trastuzumab Trastuzumab may increase the cardiotoxic activities of Lenalidomide. Approved, Investigational Typhoid Vaccine The risk or severity of adverse effects can be increased when Lenalidomide is combined with Typhoid Vaccine. Approved Varicella Zoster Vaccine (Live/Attenuated) The risk or severity of adverse effects can be increased when Lenalidomide is combined with Varicella Zoster Vaccine (Live/Attenuated). Approved Vemurafenib The serum concentration of Lenalidomide can be increased when it is combined with Vemurafenib. Approved Yellow Fever Vaccine The risk or severity of adverse effects can be increased when Lenalidomide is combined with Yellow Fever Vaccine. Approved, Investigational Zeranol Zeranol may increase the thrombogenic activities of Lenalidomide. Vet Approved - Food Interactions
- When given with a fatty meal, the extent of absorption is reduced.
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
- List A, Kurtin S, Roe DJ, Buresh A, Mahadevan D, Fuchs D, Rimsza L, Heaton R, Knight R, Zeldis JB: Efficacy of lenalidomide in myelodysplastic syndromes. N Engl J Med. 2005 Feb 10;352(6):549-57. [PubMed:15703420]
- 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. [PubMed:16569772]
- Anderson KC: Lenalidomide and thalidomide: mechanisms of action--similarities and differences. Semin Hematol. 2005 Oct;42(4 Suppl 4):S3-8. [PubMed:16344099]
- External Links
- Human Metabolome Database
- HMDB0014623
- KEGG Drug
- D04687
- PubChem Compound
- 216326
- PubChem Substance
- 46505725
- ChemSpider
- 187515
- BindingDB
- 65454
- ChEBI
- 63791
- ChEMBL
- CHEMBL848
- Therapeutic Targets Database
- DAP001255
- PharmGKB
- PA162363968
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Lenalidomide
- ATC Codes
- L04AX04 — Lenalidomide
- AHFS Codes
- 10:00.00 — Antineoplastic Agents
- FDA label
- Download (400 KB)
- MSDS
- Download (225 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Celgene corp
- Celgene Corporation
- Packagers
- Celgene
- Norwich Pharmaceuticals Inc.
- Penn Pharmaceutical Services Ltd.
- Dosage forms
Form Route Strength Capsule Oral 10 mg/1 Capsule Oral 10 mg Capsule Oral 15 mg/1 Capsule Oral 15 mg Capsule Oral 2.5 mg/1 Capsule Oral 2.5 mg Capsule Oral 20 mg/1 Capsule Oral 20 mg Capsule Oral 25 mg Capsule Oral 25 mg/1 Capsule Oral 5 mg Capsule Oral 5 mg/1 Capsule Oral 7.5 mg - Prices
Unit description Cost Unit Revlimid 25 mg capsule 411.71USD capsule Revlimid 15 mg capsule 407.7USD capsule Revlimid 10 mg capsule 406.05USD capsule Revlimid 5 mg capsule 388.0USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) CA2477301 No 2009-09-01 2023-04-13 Canada CA2342974 No 2005-08-16 2014-02-24 Canada US6045501 No 1998-08-28 2018-08-28 US US6315720 No 2000-10-23 2020-10-23 US US6561976 No 1998-08-28 2018-08-28 US US6561977 No 2000-10-23 2020-10-23 US US6755784 No 2000-10-23 2020-10-23 US US6908432 No 1998-08-28 2018-08-28 US US8204763 No 1998-08-28 2018-08-28 US US8315886 No 2000-10-23 2020-10-23 US US8626531 No 2000-10-23 2020-10-23 US US8589188 No 1998-08-28 2018-08-28 US US7468363 No 2003-10-07 2023-10-07 US US6281230 No 1996-07-24 2016-07-24 US US8530498 No 2003-05-15 2023-05-15 US US6555554 No 1996-07-24 2016-07-24 US US7189740 No 2003-04-11 2023-04-11 US US7968569 No 2003-10-07 2023-10-07 US US8404717 No 2003-04-11 2023-04-11 US US8648095 No 2003-05-15 2023-05-15 US US8741929 No 2008-03-08 2028-03-08 US US9101622 No 2003-05-15 2023-05-15 US US9101621 No 2003-05-15 2023-05-15 US US9056120 No 2003-04-11 2023-04-11 US US5635517 No 1999-10-04 2019-10-04 US US7119106 No 1996-07-24 2016-07-24 US US7465800 No 2007-04-27 2027-04-27 US US7855217 No 2004-11-24 2024-11-24 US US8288415 No 1996-07-24 2016-07-24 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble 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 -0.4 Not Available - Predicted Properties
Property Value Source Water Solubility 2.33 mg/mL ALOGPS logP -0.43 ALOGPS logP -0.71 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 11.61 ChemAxon pKa (Strongest Basic) 2.31 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 92.5 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 68.3 m3·mol-1 ChemAxon Polarizability 25.55 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.9372 Caco-2 permeable - 0.5981 P-glycoprotein substrate Substrate 0.6845 P-glycoprotein inhibitor I Inhibitor 0.6012 P-glycoprotein inhibitor II Non-inhibitor 0.8927 Renal organic cation transporter Non-inhibitor 0.726 CYP450 2C9 substrate Non-substrate 0.8861 CYP450 2D6 substrate Non-substrate 0.7878 CYP450 3A4 substrate Substrate 0.5855 CYP450 1A2 substrate Non-inhibitor 0.8746 CYP450 2C9 inhibitor Non-inhibitor 0.8405 CYP450 2D6 inhibitor Non-inhibitor 0.8806 CYP450 2C19 inhibitor Non-inhibitor 0.78 CYP450 3A4 inhibitor Non-inhibitor 0.7469 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.843 Ames test Non AMES toxic 0.8268 Carcinogenicity Non-carcinogens 0.9068 Biodegradation Not ready biodegradable 0.9967 Rat acute toxicity 2.5145 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9803 hERG inhibition (predictor II) Non-inhibitor 0.5098
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0002-1920000000-c10c48acd9b8123e3505
Taxonomy
- 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 / Isoindolone / Isoindole / Piperidinedione / Delta-lactam / Piperidinone / Piperidine / Benzenoid / Carboxylic acid imide / Dicarboximide show 18 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- dicarboximide, aromatic amine, piperidones, isoindoles (CHEBI:63791)
Targets
- Kind
- Protein
- Organism
- Human
- 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
- 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. [PubMed:22966948]
- Kind
- Protein
- Organism
- Human
- 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
- 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. [PubMed:19370685]
- Melchert M, List A: The thalidomide saga. Int J Biochem Cell Biol. 2007;39(7-8):1489-99. Epub 2007 Jan 30. [PubMed:17369076]
- Kind
- Protein
- Organism
- Human
- 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
- 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. [PubMed:18805433]
- Kind
- Protein
- Organism
- Human
- 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
- 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. [PubMed:15598423]
- 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. [PubMed:12720152]
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- 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
Drug created on June 13, 2005 07:24 / Updated on June 18, 2018 06:30