All Photos(1)

T150

Sigma-Aldrich

(−)-Thalidomide

>98%, solid

Synonym(s):
S(−)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione
Empirical Formula (Hill Notation):
C13H10N2O4
CAS Number:
Molecular Weight:
258.23
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

>98%

form

solid

optical activity

[α]23/D −62.6°, c = 2 in DMF(lit.)

application(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

Related Categories

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.

Packaging

10 mg in poly bottle
25, 100 mg in glass bottle

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

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Repr. 1B

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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
Thalidomide: the tragedy of birth defects and the effective treatment of disease
Kim JH and Scialli AR
Toxicological Sciences, 122(1) (2011)
Thalidomide-induced teratogenesis: History and mechanisms
Vargesson N
Birth Defects Research Part C: Embryo Today - Reviews, 105(2) (2015)
Kanandra T Bertoncello et al.
Progress in neuro-psychopharmacology & biological psychiatry, 93, 39-45 (2019-03-19)
Ethanol is one of the most consumed substance worldwide that impairs learning and memory processes, resulting in amnesia or blackout. Due to the genetic conservation, rich behavioral repertoire, and high pharmacological tractability, the zebrafish (Danio rerio) has emerged as a

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