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T150

(−)-Thalidomide

>98%, solid

Sinónimos:

S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

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Fórmula empírica (notación de Hill):
C13H10N2O4
Número CAS:
841-67-8
Peso molecular:
258.23
NACRES:
NA.77
PubChem Substance ID:
24899969
UNSPSC Code:
12352207
MDL number:
MFCD00210219
Assay:
>98%
Form:
solid
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ligand

thalidomide

assay

>98%

form

solid

optical activity

[α]23/D −62.6°, c = 2 in DMF(lit.)

reaction suitability

reagent type: ligand

technique(s)

cell culture | embryo: suitable

color

white

solubility

DMSO: soluble, H2O: insoluble, ethanol: insoluble

originator

Celgene

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-/m0/s1

InChI key

UEJJHQNACJXSKW-VIFPVBQESA-N

Gene Information

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

General description

Thalidomide is a stereoisomer, which exists in two enantiomeric states. The S enantiomer is teratogenic. Thalidomide consists of two linked rings, a phthalimide and glutarimide ring.

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 the biosynthesis of tumor necrosis factor α (TNF-α), which is essential for inflammatory response. It is an anti-emetic drug and is used to treat morning sickness in pregnant women. Thalidomide is also used to treat leprosy, multiple myeloma, Crohn′s disease and human immunodeficiency virus (HIV) infection. Thalidomide also inhibits angiogenesis. It is associated with several diseases such as, peripheral neuropathy, facial palsies, Duane syndrome and autism.

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, but is insoluble in water and ethanol.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H302,H360

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Clase de almacenamiento

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

wgk

WGK 3

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
0000200389
0000184447
0000184447
0000200389
0000144132

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