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HomeProduct name list(-)-THALIDOMIDE

(-)-THALIDOMIDE

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

  • CAS NO.:841-67-8
  • Empirical Formula: C13H10N2O4
  • Molecular Weight: 258.23
  • MDL number: MFCD00210219
  • EINECS: 635-910-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 20:33:22
(-)-THALIDOMIDE Structural

What is (-)-THALIDOMIDE?

Chemical properties

Needles

The Uses of (-)-THALIDOMIDE

Optically active isomer of Thalidomide, which inhibits FGF-induced angiogenesis. Inhibits replication of human immunodeficiency virus type 1. Teratogenic sedative

The Uses of (-)-THALIDOMIDE

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.

What are the applications of Application

(S)-(?)-Thalidomide is an optically active isomer of Thalidomide

Definition

ChEBI: A 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione that has S-configuration at the chiral centre.

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.

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.

Properties of (-)-THALIDOMIDE

Melting point: 269-271°C
Boiling point: 401.48°C (rough estimate)
Density  1.2944 (rough estimate)
refractive index  1.5300 (estimate)
storage temp.  -20°C Freezer
solubility  DMSO: soluble
form  solid
pka 10.70±0.40(Predicted)
color  white
optical activity [α]23/D 62.6°, c = 2 in DMF(lit.)

Safety information for (-)-THALIDOMIDE

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H360:Reproductive toxicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for (-)-THALIDOMIDE

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