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Details

Stereochemistry RACEMIC
Molecular Formula C13H10N2O4
Molecular Weight 258.2295
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THALIDOMIDE

SMILES

O=C1N(C2CCC(=O)NC2=O)C(=O)C3=C1C=CC=C3

InChI

InChIKey=UEJJHQNACJXSKW-UHFFFAOYSA-N
InChI=1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)

HIDE SMILES / InChI

Description

Thalidomide is an immunomodulatory agent with a spectrum of activity that is not fully characterized. Thalidomide is racemic — it contains both left and right-handed isomers in equal amounts: one enantiomer is effective against morning sickness, and the other is teratogenic. The enantiomers are converted to each other in vivo. That is, if a human is given D-thalidomide or L-thalidomide, both isomers can be found in the serum. Hence, administering only one enantiomer will not prevent the teratogenic effect in humans. In patients with erythema nodosum leprosum (ENL) the mechanism of action is not fully understood. Available data from in vitro studies and preliminary clinical trials suggest that the immunologic effects of this compound can vary substantially under different conditions, but may be related to suppression of excessive tumor necrosis factor-alpha (TNF-a) production and down-modulation of selected cell surface adhesion molecules involved in leukocyte migration. For example, administration of thalidomide has been reported to decrease circulating levels of TNF-a in patients with ENL, however, it has also been shown to increase plasma TNF-a levels in HIV-seropositive patients. As a cancer treatment, the drug may act as a VEGF inhibitor. Thalidomide is used for the acute treatment of the cutaneous manifestations of moderate to severe erythema nodosum leprosum (ENL). Also for use as maintenance therapy for prevention and suppression of the cutaneous manifestations of ENL recurrence. Thalidomide is sold under the brand name Immunoprin, among others.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Randomized clinical trial of thalidomide, cyclosporine, and prednisone versus cyclosporine and prednisone as initial therapy for chronic graft-versus-host disease.
2001
Thalidomide in gastrointestinal disorders.
2001
Managing cancer-related anorexia/cachexia.
2001
Aza analogues of thalidomide: synthesis and evaluation as inhibitors of tumor necrosis factor-alpha production in vitro.
2001 Apr
A cybernetic theory of morality and moral autonomy.
2001 Apr
Current management of cancer-associated anorexia and weight loss.
2001 Apr
The irreplaceable image. Thalidomide in refractory myeloma patients: early changes in bone marrow cellularity.
2001 Apr
Salvage therapy with thalidomide in multiple myeloma patients relapsing after autologous peripheral blood stem cell transplantation.
2001 Apr
Thalidomide treatment of resistant or relapsed multiple myeloma patients.
2001 Apr
Low-dose thalidomide plus dexamethasone is an effective salvage therapy for advanced myeloma.
2001 Apr
Differential effects of thalidomide on angiogenesis and tumor growth in mice.
2001 Apr
[Teratology, 40 years after the thalidomide tragedy].
2001 Feb
Pharmacotherapeutic options in inflammatory bowel disease: an update.
2001 Feb
Scleroderma.
2001 Feb
Efficacy of long-term treatment with thalidomide in children and young adults with Crohn disease: preliminary results.
2001 Feb
Differential effect of thalidomide and dexamethasone on the transcription factor NF-kappa B.
2001 Jan
Thalidomide as an anti-angiogenic agent in relapsed gliomas.
2001 Jan
[New concepts about atopic dermatitis].
2001 Jan-Feb
Clinical aspects and management of AIDS-related Kaposi's sarcoma.
2001 Jul
Thalidomide and immunomodulatory derivatives augment natural killer cell cytotoxicity in multiple myeloma.
2001 Jul 1
Extended survival in advanced and refractory multiple myeloma after single-agent thalidomide: identification of prognostic factors in a phase 2 study of 169 patients.
2001 Jul 15
Thalidomide and prednisolone inhibit growth factor-induced human retinal pigment epithelium cell proliferation in vitro.
2001 Jul-Aug
Thalidomide-induced amenorrhoea: two cases.
2001 Jun
[Thalidomide and cancer--revival of a drug].
2001 Jun
Alpha-glucosidase inhibitors with a 4,5,6,7-tetrachlorophthalimide skeleton pendanted with a cycloalkyl or dicarba-closo-dodecaborane group.
2001 Jun
Disease controlling antirheumatic therapy in spondyloarthropathy.
2001 Jun
Thalidomide dose proportionality assessment following single doses to healthy subjects.
2001 Jun
Color Doppler ultrasonography of the superior mesenteric artery for prenatal ultrasonographic diagnosis of a left-sided congenital diaphragmatic hernia.
2001 Jun
Effectors of inflammation in actinic prurigo.
2001 Jun
Deep venous thrombosis and thalidomide therapy for multiple myeloma.
2001 Jun 21
[Thalidomide and thrombosis: three observations].
2001 Jun 9
[Management of severe skin disorders in sarcoidosis].
2001 Mar
Thalidomide-induced sensory neuropathy.
2001 Mar
Targeting of vasculature in cancer and other angiogenic diseases.
2001 Mar
[The return of thalidomide].
2001 Mar
Thalidomide: near complete regression of extramedullary bulk in refractory multiple myeloma.
2001 Mar 10
[Comparative treatment between thalidomide and transfer factor in severe atopic dermatitis].
2001 Mar-Apr
Successful thalidomide treatment of severe infantile Behçet disease.
2001 Mar-Apr
[Sarcoidosis: thalidomide treatment in ten patients].
2001 May
Possible role of adjunctive thalidomide therapy in the resolution of a massive intracranial tuberculous abscess.
2001 May
Enantioseparation of aminoglutethimide and thalidomide by high performance liquid chromatography or supercritical fluid chromatography on mono-2 and mono-6-O-pentenyl-beta-cyclodextrin-based chiral stationary phases.
2001 May
Is infliximab effective for induction of remission in patients with ulcerative colitis?
2001 May
Thalidomide in multiple myeloma: lack of response of soft-tissue plasmacytomas.
2001 May
Transcending conventional therapies: the role of biologic and other novel therapies.
2001 May
Synthesis and immunological activity of water-soluble thalidomide prodrugs.
2001 May
Thalidomide and its dermatologic uses.
2001 May
Intractable insomnia after cessation of treatment with thalidomide.
2001 May
Novel approaches to the treatment of chronic graft-versus-host disease.
2001 May
Neurobehavioral teratogenic effects of thalidomide in rats.
2001 May-Jun
Pilot study using the combination of methotrexate and thalidomide in the treatment of rheumatoid arthritis.
2001 May-Jun
Patents

Sample Use Guides

In Vivo Use Guide
MM: 200 mg orally once daily. The recommended dose of dexamethasone is 40 mg/day on days 1-4, 9-12, and 17-20 every 28 days. • ENL: 100 to 300 mg/day for an episode of cutaneous ENL. Up to 400 mg/day for severe cutaneous ENL.
Route of Administration: Oral
In Vitro Use Guide
The minimum dose of thalidomide used (1 uM) inhibited TNF-α production in HTLV-1-infected subjects in vitro.
Name Type Language
THALIDOMIDE
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
K-17
Code English
KEVADON
Brand Name English
THALIDOMIDE [JAN]
Common Name English
THALIDOMIDE [HSDB]
Common Name English
THALIDOMIDE [MART.]
Common Name English
2,6-DIOXO-3-PHTHALIMIDOPIPERIDINE
Systematic Name English
CONTERGAN
Brand Name English
THALIDOMIDE [VANDF]
Common Name English
DISTAVAL
Brand Name English
THALIDOMIDE [USP]
Common Name English
(+/-)-N-(2,6-DIOXO-3-PIPERIDYL)PHTHALIMIDE
Systematic Name English
PHARMION
Brand Name English
THALIDOMIDE [USAN]
Common Name English
N-PHTHALYLGLUTAMIC ACID IMIDE
Common Name English
.ALPHA.-PHTHALIMIDOGLUTARIMIDE
Common Name English
NSC-527179
Code English
MYRIN
Brand Name English
NSC-66847
Code English
THALIDOMIDE [INN]
Common Name English
THALIDOMIDE [USP-RS]
Common Name English
NEUROSEDYN
Brand Name English
THALIDOMIDE [ORANGE BOOK]
Common Name English
1H-ISOINDOLE-1,3(2H)-DIONE, 2-(2,6-DIOXO-3-PIPERIDINYL)-, (+/-)-
Systematic Name English
CELGENE
Brand Name English
THALOMID
Brand Name English
2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE
Systematic Name English
SOFTENON
Brand Name English
.ALPHA.-(N-PHTHALIMIDO)GLUTARIMIDE
Common Name English
PANTOSEDIV
Brand Name English
THALIDOMIDE [EMA EPAR]
Common Name English
3-PHTHALIMIDOGLUTARIMIDE
Systematic Name English
THALED
Brand Name English
THALIDOMIDE [WHO-DD]
Common Name English
THALIDOMIDE [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 43890
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 80194
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 30788
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
WHO-ATC L04AX02
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 115598
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 43790
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
NDF-RT N0000008663
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
WHO-VATC QL04AX02
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 90795
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
EU-Orphan Drug EU/3/01/067
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
NDF-RT N0000008663
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 585417
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 110197
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 72092
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
NCI_THESAURUS C129820
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 114998
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
NCI_THESAURUS C1742
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 121898
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 187204
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 94995
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
NCI_THESAURUS C574
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 32188
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
EMA ASSESSMENT REPORTS THALIDOMIDE CELGENE (AUTHORIZED: MUTIPLE MYELOMA)
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
NCI_THESAURUS C54677
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
FDA ORPHAN DRUG 82594
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
LIVERTOX 948
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
Code System Code Type Description
CAS
50-35-1
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
RXCUI
10432
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY RxNorm
EPA CompTox
50-35-1
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
MESH
D013792
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
PUBCHEM
5426
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
DRUG BANK
DB01041
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
IUPHAR
7327
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
ChEMBL
CHEMBL468
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
WIKIPEDIA
THALIDOMIDE
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
EVMPD
SUB10958MIG
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
NCI_THESAURUS
C870
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-031-1
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
INN
762
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY
MERCK INDEX
M10673
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY Merck Index
HSDB
50-35-1
Created by admin on Mon Oct 21 20:44:36 UTC 2019 , Edited by admin on Mon Oct 21 20:44:36 UTC 2019
PRIMARY