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Merck
CN

T151

(+)-Thalidomide

≥98% (HPLC), powder

Synonym(s):

R-(+)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

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About This Item

Empirical Formula (Hill Notation):
C13H10N2O4
CAS Number:
2614-06-4
Molecular Weight:
258.23
NACRES:
NA.77
PubChem Substance ID:
24899975
UNSPSC Code:
12352200
MDL number:
MFCD00210220

Key Documents

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Product Name

(+)-Thalidomide, ≥98% (HPLC), powder

InChI key

UEJJHQNACJXSKW-SECBINFHSA-N

SMILES string

O=C1CC[C@@H](N2C(=O)c3ccccc3C2=O)C(=O)N1

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)/t9-/m1/s1

ligand

thalidomide

assay

≥98% (HPLC)

form

powder

reaction suitability

reagent type: ligand

color

white to beige

solubility

DMSO: 15 mg/mL, clear

originator

Celgene

storage temp.

room temp

Quality Level

200

Gene Information

human ... LITAF(9516), TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)

Related Categories

Application

Thalidomide has been used to study its teratogenic effects in chicken embryos and human embryonic cells. This study reported that thalidomide causes limb defects by stabilizing PTEN, inhibiting the expression of Akt and activating caspase-dependent apoptosis. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.

Biochem/physiol Actions

(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). (R)-Thalidomide is called "safe enantiomer", but it can be converted in the body to (S)-isomer.

Features and Benefits

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Thalidomide is soluble in DMSO at a concentration that is greater than or equal to 20 mg/ml. It is insoluble in ethanol and water.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H302,H360

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000203716
0000186991
0000186991
0000203716
0000144680

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Jianhui Zhao et al.
Neurochemical research, 41(12), 3171-3180 (2016-08-31)
Opioid analgesics have less efficacy in diabetic neuropathy treatment, and tolerance often occurs after chronic usage. Given that thalidomide can potentiate the morphine efficacy in diabetic neuropathy treatment, we investigated the effects of intrathecal administrations of thalidomide on morphine tolerance
Jürgen Knobloch et al.
Molecular pharmaceutics, 5(6), 1138-1144 (2009-05-13)
Thalidomide as an effective treatment for multiple myeloma and leprosy has also caused birth defects in thousands of children five decades ago particularly in Europe. Thus its use in humans remains limited. The rapid and fatal approval of thalidomide at
Jürgen Knobloch et al.
Molecular and cellular biology, 28(2), 529-538 (2008-01-08)
Thalidomide, a drug used for the treatment of multiple myeloma and inflammatory diseases, is also a teratogen that causes birth defects, such as limb truncations and microphthalmia, in humans. Thalidomide-induced limb truncations result from increased cell death during embryonic limb
Agata Kowalczyk et al.
Biosensors & bioelectronics, 167, 112446-112446 (2020-08-21)
Fast, simple in use and highly effective voltammetric enantiosensor dedicated for determination of thalidomide (TD) enantiomers (especially towards the toxic (S)-enantiomer) in blood plasma is still desirable. Here we have proven that newly synthesized chiral naphthalene diimide (NDI) derivatives are
S Makonkawkeyoon et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(13), 5974-5978 (1993-07-01)
Thalidomide, a selective inhibitor of tumor necrosis factor alpha (TNF-alpha) synthesis, suppresses the activation of latent human immunodeficiency virus type 1 (HIV-1) in a monocytoid (U1) line. The inhibition is dose dependent and occurs after exposure of the cells to
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