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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=CC=CC=C13

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

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

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
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-induced amenorrhoea: two cases.
2001 Jun
[Thalidomide and cancer--revival of a drug].
2001 Jun
Deep venous thrombosis and thalidomide therapy for multiple myeloma.
2001 Jun 21
[Thalidomide and thrombosis: three observations].
2001 Jun 9
[Comparative treatment between thalidomide and transfer factor in severe atopic dermatitis].
2001 Mar-Apr
[Sarcoidosis: thalidomide treatment in ten patients].
2001 May
Neurobehavioral teratogenic effects of thalidomide in rats.
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.
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:37:18 UTC 2018
Edited
by admin
on Tue Mar 06 10:37:18 UTC 2018
Record UNII
4Z8R6ORS6L
Record Status FAILED
Record Version
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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
WHO-ATC L04AX02
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
NDF-RT N0000008663
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
WHO-VATC QL04AX02
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
NDF-RT N0000008663
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
EMA ASSESSMENT REPORTS THALIDOMIDE CELGENE (AUTHORIZED: MUTIPLE MYELOMA)
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
LIVERTOX 948
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
Code System Code Type Description
CAS
50-35-1
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
RXCUI
10432
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY RxNorm
EPA CompTox
50-35-1
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
MESH
D013792
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
PUBCHEM
5426
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY SWITZERF
DRUG BANK
DB01041
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
IUPHAR
7327
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
ChEMBL
CHEMBL468
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
WIKIPEDIA
THALIDOMIDE
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
EVMPD
SUB10958MIG
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
NCI_THESAURUS
C870
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
ECHA (EC/EINECS)
200-031-1
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
INN
762
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
MERCK INDEX
M10673
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY Merck Index
HSDB
50-35-1
Created by admin on Tue Mar 06 10:37:18 UTC 2018 , Edited by admin on Tue Mar 06 10:37:18 UTC 2018
PRIMARY
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