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T150

Sigma-Aldrich

(−)-Thalidomide

>98%, solid

Synonym(s):

S(−)-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:
841-67-8
Molecular Weight:
258.23
MDL number:
MFCD00210219
UNSPSC Code:
12352207
PubChem Substance ID:
24899969
NACRES:
NA.77

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)

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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.

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

hcodes

H302,H360

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

wgk_germany

WGK 3

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Thalidomide-induced teratogenesis: History and mechanisms
Vargesson N
Birth Defects Research Part C: Embryo Today - Reviews, 105(2) (2015)
Thalidomide: the tragedy of birth defects and the effective treatment of disease
Kim JH and Scialli AR
Toxicological Sciences, 122(1) (2011)
Guo-Liang Duan et al.
International journal of biological macromolecules, 137, 1112-1120 (2019-07-05)
Six polysaccharides (SF-FB11, SF-HW21, SF-CA31, SF-HA41, SF-FF51, and SF-FR61) of similar molecular weights (MW) (30-50 kDa) were extracted from the fermentation liquor, mycelia, and basidiomata of Sparassis latifolia by different methods. Structural analyses of these purified polysaccharides indicated that they were
John H Sampson et al.
Molecular cancer therapeutics, 8(10), 2773-2779 (2009-10-15)
Conventional therapies for glioblastoma multiforme (GBM) fail to target tumor cells exclusively, such that their efficacy is ultimately limited by nonspecific toxicity. Immunologic targeting of tumor-specific gene mutations, however, may allow more precise eradication of neoplastic cells. The epidermal growth
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
View All Related Papers

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