Ligand id: 7327

Name: thalidomide

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 87.04
Molecular weight 258.06
XLogP 1.35
No. Lipinski's rules broken 0

Molecular properties generated using the CDK

No information available.
Summary of Clinical Use
Thalidomide was originally used treat nausea and alleviate morning sickness in pregnant women. Unfortunately the drug was found to be a powerful human teratogen, causing severe embryopathy, principally malformation of the limbs (phocomelia). This drug has undergone a remarkable metamorphosis, with thalidomide now being repurposed as a treatment for certain cancers (eg multiple myeloma, in combination with dexamethasone, or melphalan and prednisone) and for erythema nodosum leprosum (ENL), a complication of leprosy. As a condition of drug approval, authorising agencies stipulate that female patients with childbearing potential, requiring thalidomide treatment, be advised to use multiple forms of contraception and/or be counselled and educated regarding the risks associated with taking the drug, and the importance of avoiding pregnancy. They may also be offered regular pregnancy tests.
Mechanism Of Action and Pharmacodynamic Effects
As an antineoplastic agent, thalidomide appears to inhibit the angiogenesis essential for tumour growth. Anti-inflammatory action may be due to supression of production of pro-inflammatory cytokines and enhanced production of anti-inflammatory cytokines such as IL-10 [5]. The primary target of thalidomide may be the protein cereblon (CRBM, Q96SW2) [4,6], which has been linked to the teratogenic activity of the thalidomide-like drugs [1-2]. Cereblon has multiple actions, including participation in protein ubiquitination complexes and regulation of potassium channels [1,3].
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