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Structural formula
Structure of the two enantiomers of lenalidomide
1: 1 mixture of ( R ) -form (left) and ( S ) -form (right)
Non-proprietary name Lenalidomide
other names
  • ( RS ) -3- (7-Amino-3-oxo-1 H -isoindol-2-yl) piperidin-2,6-dione ( IUPAC )
  • (±) -3- (7-amino-3-oxo-1 H -isoindole-2-yl) -piperidine-2,6-dione
  • rac -3- (7-amino-3-oxo-1 H -isoindole-2-yl) -piperidine-2,6-dione
Molecular formula C 13 H 13 N 3 O 3
Brief description

almost white to pale yellow powder

External identifiers / databases
CAS number 191732-72-6
EC number 691-297-1
ECHA InfoCard 100.218.924
PubChem 216326
DrugBank DB00480
Wikidata Q425681
Drug information
ATC code

L04 AX04

Drug class


Molar mass 259.26 g · mol -1
Melting point

269-271 ° C


More soluble in organic solvents, but shows the best solubility in 0.1 N HCl buffer solution

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning


H and P phrases H: 317-319
P: 280-305 + 351 + 338-422
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lenalidomide (trade name: Revlimid , manufacturer: Celgene ) is a drug from the group of immunomodulators . It is structurally related to thalidomide and pomalidomide and, like them, is used to treat multiple myeloma , myelodyplastic syndromes (MDS) and mantle cell lymphoma . Lenalidomide has been designated as an orphan medicinal product by the Committee for Medicinal Products for Human Use (CHMP) of the European Medicines Agency and registered as such in the Community register of the European Union.

Application areas / approval status

Lenalidomide is indicated for the treatment of adult patients with untreated multiple myeloma who cannot be transplanted.

Lenalidomide is approved in the United States, the European Union, Switzerland, Argentina and Canada for combination therapy with dexamethasone in patients with multiple myeloma who have already received standard therapy. In addition, lenalidomide in conjunction with dexamethasone is approved in Australia for the treatment of multiple myeloma patients whose disease got worse after treatment.

The New England Journal of Medicine (NEJM) published the results of three Phase III studies of lenalidomide in subjects with newly diagnosed multiple myeloma in May 2012.

In 2019, Piechotta et al. conducted a Cochrane review to evaluate the comparability of lenalidomide with other drugs used to treat multiple myeloma. This was compared with therapy with melphalan and prednisone alone. The results were as follows: lenalidomide plus dexamethasone and the continued administration of bortezomib plus lenalidomide plus dexamethasone are likely to cause an increase in overall survival. Lenalidomide plus dexamethasone and the continued administration of bortezomib plus lenalidomide plus dexamethasone may cause a large increase in progression-free survival. The administration of lenalidomide plus dexamethasone may cause a reduction in polyneuropathies. The other combination was not evaluated here. Lenalidomide plus dexamethasone and the continued administration of bortezomib plus lenalidomide plus dexamethasone caused a marked increase in patient discontinuation due to adverse events.

Lenalidomide is indicated for the treatment of patients with transfusion-dependent anemia due to low- or intermediate-1 risk myelodysplastic syndromes associated with an isolated 5q deletion as a cytogenetic abnormality, when other treatment options are inadequate or inadequate.

Various studies are currently examining the extent to which lenalidomide can be used for maintenance therapy or therapy of chronic lymphatic leukemia (CLL). The ORIGIN study (planned to run until 2018) to test the safety and efficacy of lenalidomide as a first-line therapy for CLL was canceled by the US Food and Drug Administration (FDA) due to an increased mortality rate . The FDA is therefore calling on doctors not to prescribe lenalidomide for off-label use in CLL.

Mechanism of action

Like thalidomide and pomalidomide, lenalidomide belongs to a group of perorally bioavailable immunomodulatory drugs that the pharmaceutical company Celgene has registered under the brand name IMiDs . Its effect is based on various mechanisms:

At the molecular level, the action of lenalidomide assumes that it causes the protein kinase casein kinase-1-alpha (CK1α) to ubiquitinate , causing it to break down in the proteasome. CK1α is a serine - threonine kinase that activates TP53, which in turn has an anti-apoptotic effect. It also activates the oncogenic Wnt / β-catenin signaling pathway . The gene for CK1α is called CSNK1A1 and is located on chromosome 5 in section 5q. This explains why lenalidomide works very well in a myelodysplastic syndrome with 5q deletion (del [5q]) and corresponding haploinsufficiency .

Safety Precautions and Restrictions on Use

When using lenalidomide, important aspects must be observed. Because lenalidomide is believed to have teratogenic effects on humans, it includes a pregnancy prevention program for women of childbearing potential and their partners. A possible myelosuppression makes weekly blood counts necessary for the first eight weeks of treatment. Furthermore, the increased risk of venous thromboembolism with the possible use of antithrombotic prophylaxis and the dose reduction in case of renal insufficiency must be taken into account. In Germany, the dispensing of drugs containing lenalidomide is regulated by Section 3a of the Medicinal Prescription Ordinance and is subject to official monitoring, which is why the doctor must use the so-called T-prescription for the prescription . The doctor must ensure that the safety measures in accordance with the current product information are observed, in particular that a pregnancy prevention program is carried out if necessary. He must also note on the prescription whether the treatment takes place within or outside ( off-label use ) of the respective approved application areas.

In December 2012, the manufacturer Celgene sent a notice to members of the health professions ( Rote-Hand-Brief ) on the risk of developing liver disease in connection with the use of lenalidomide in the presence of other risk factors.

Side effects

The most common side effects observed are a decrease in white blood cells ( neutropenia ), blood platelets ( thrombocytopenia ) and red blood cells ( anemia ), tiredness, weakness, nausea, constipation, diarrhea, muscle cramps, swelling in the arms and legs and a rash.

Chemical properties

Lenalidomide is chiral and can therefore exist in the optically active enantiomeric forms ( S ) - (-) and ( R ) - (+), the racemate [1: 1 mixture of ( S ) - (-) - form is used pharmaceutically and ( R ) - (+) - form]. Lenalidomide is readily soluble in 0.1 N hydrochloric acid.

Trade names

Revlimid (EU, CH, USA)

Individual evidence

  1. a b FDA Drug Details Revlimid (lenalidomide)
  2. a b c Safety data sheet 3- (4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl) piperidine-2,6-dione (PDF) from Matrix Scientific, accessed on August 30, 2017 .
  3. a b Summary of the EPAR for the public. (PDF; 60 kB) European Medicines Agency (German).
  4. Orphan Designation (EU / 3/03/177) by the European Commission (English).
  5. Orphan Designation (EU / 3/07/494) by the European Commission (English).
  6. a b Technical information on Revlimid . September 2016.
  7. Product information from the European Medicines Agency (English).
  8. Meletios Dimopoulos et al .: Lenalidomide plus Dexamethasone for Relapsed or Refractory Multiple Myeloma . In: N Engl J Med . No. 357 , 2007, p. 2123–2132 , doi : 10.1056 / NEJMoa070594 (free full text).
  9. Donna M. Weber et al .: Lenalidomide plus Dexamethasone for Relapsed Multiple Myeloma in North America . In: N Engl J Med . No. 357 , 2007, p. 2133–2142 , doi : 10.1056 / NEJMoa070596 (free full text).
  10. ^ Antonio Palumbo et al .: Continuous Lenalidomide Treatment for Newly Diagnosed Multiple Myeloma . In: N Engl J Med . No. 366 , 2012, p. 1759–1769 , doi : 10.1056 / NEJMoa1112704 (free full text).
  11. ^ Philip L. McCarthy et al .: Lenalidomide after Stem-Cell Transplantation for Multiple Myeloma . In: N Engl J Med . No. 366 , 2012, p. 1770–1781 , doi : 10.1056 / NEJMoa1114083 (free full text).
  12. Attal, Michel et al .: Lenalidomide Maintenance after Stem-Cell Transplantation for Multiple Myeloma . In: N Engl J Med . No. 366 , 2012, p. 1782–1791 , doi : 10.1056 / NEJMoa1114138 (free full text).
  13. Vanessa Piechotta, Tina Jakob, Peter Langer, Ina Monsef, Christof Scheid: Multiple drug combinations of bortezomib, lenalidomide, and thalidomide for first-line treatment in adults with transplant-ineligible multiple myeloma: a network meta-analysis . In: Cochrane Database of Systematic Reviews . November 25, 2019, doi : 10.1002 / 14651858.CD013487 ( wiley.com [accessed July 16, 2020]).
  14. Studies in Clinic I for Internal Medicine, Cologne University Hospital . ( Memento of December 10, 2012 in the Internet Archive ; PDF; 67 kB).
  15. FDA Statement: FDA halts clinical trial of drug Revlimid (lenalidomide) for chronic lymphocytic leukemia due to safety concerns .
  16. Benjamin L. Ebert, Jan Krönke: Inhibition of Casein Kinase 1 Alpha in acute myeloid leukemia . New England Journal of Medicine 2018, Volume 279, Issue 19, Nov. 8, 2018, pages 1873-1874, [DOI: 10.1056 / NEJMcibr1811318].
  17. Rote Hand Info from Celgene June 2008, akdae.de (PDF; 1.5 MB).
  18. Red Hand Letter from Celgene, December 2012. Retrieved December 10, 2012 .