Name | (S)-thalidomide |
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Synonyms |
(-)-N-[(S)-2,6-Dioxo-3-piperidinyl]phthalimide
(-)-Thalidomide 6-dioxo-3-piperidyl)-n-(l-(-)-phthalimid INHIBITOR OF ANGIOG EN S(-)-2-(2,6-DIOXO-3-PIPERIDINYL)-1H-ISOINDOLE-1,3(2H)-DIONE (3S)-3-(1,3-Dioxo-2H-isoindole-2-yl)piperidine-2,6-dione 1H-Isoindole-1,3(2H)-dione,2-[(3S)-2,6-dioxo-3-piperidinyl]- (-)-THALIDOMIDE &N-[(S)-2,6-Dioxopiperidine-3-yl]phthalimide L-thalidomide 6-dioxo-3-piperidinyl)-3(2h)-dion(s)-1h-isoindole-2-(2 2-[(3S)-2,6-Dioxo-3-piperidyl]-1H-isoindole-1,3(2H)-dione (-)-(S)-1,3-dioxo-2-(2',6'-dioxopiperidin-3'-yl)isoindol MFCD00210219 |
Description | (S)-Thalidomide ((S)-(-)-Thalidomide) is the S-enantiomer of Thalidomide. (S)-Thalidomide has immunomodulatory, anti-inflammatory, antiangiogenic and pro-apoptotic effects[1][2][3]. (S)-Thalidomide induces teratogenic effects by binding to cereblon (CRBN) [4]. |
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Related Catalog | |
Target |
Apoptosis[1] |
In Vitro | (S)-Thalidomide treatment results in a reduction in cell viability in U266 cells with an IC50 of 362 μM[1]. (S)-Thalidomide treatment increased apoptosis in a dose-dependent manner in U266 cells[1]. There are changes in the expression profile of genes involved in angiogenesis and apoptosis, but the changes are most dramatic in the apoptotic genes. In particular, the expression of I-κB kinase is decreased by two-fold, which is associated with a four-fold decrease in NF-κB expression. (S)-Thalidomide increases the Bax:Bcl-2 ratio, also increases I-kB protein levels, and decreases NF-kB activity. A dramatic decrease in Bcl-2 expression with (S)-Thalidomide suggests a possible enhancement of cytotoxic effect if combined with other cytotoxic agents[1]. Cell Viability Assay[1] Cell Line: U266 MM cells Concentration: 0 µM, 10 µM, 100 µM, 150 µM, 200 µM, 1000 µM Incubation Time: 3 days Result: A reduction in cell viability was observed in U266 cells. Apoptosis Analysis[1] Cell Line: U266 MM cells Concentration: 100 µM, 150 µM, 200 µM, 1000 µM Incubation Time: 3 days Result: Increased apoptosis in U266 cells. |
In Vivo | Thalidomide does cause limb reduction defects in chick embryos as long as the embryos are directly exposed to the drug. The most useful techniques are implanting Thalidomide-soaked beads into the embryo immediately adjacent to the limb territory or soaking presumptive chick limb territories in Thalidomide and then grafting the explants to a host embryo celom. Thalidomide affects the chick limb grafted to a host embryo in a dose response fashion. Furthermore, (S)-Thalidomide is more teratogenic than (R)-Thalidomide[1]. |
References |
Density | 1.503g/cm3 |
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Boiling Point | 509.7ºC at 760 mmHg |
Melting Point | 269-271ºC |
Molecular Formula | C13H10N2O4 |
Molecular Weight | 258.22900 |
Flash Point | 262.1ºC |
Exact Mass | 258.06400 |
PSA | 83.55000 |
LogP | 0.35450 |
Index of Refraction | 1.646 |
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
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Symbol |
GHS07, GHS08 |
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Signal Word | Danger |
Hazard Statements | H302-H360 |
Precautionary Statements | P201-P308 + P313 |
Personal Protective Equipment | Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges |
Hazard Codes | T: Toxic; |
Risk Phrases | R61 |
Safety Phrases | 53-36/37/39-45 |
RIDADR | UN 2811 6.1/PG 2 |
RTECS | TI4925050 |
HS Code | 2925190090 |
Precursor 8 | |
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DownStream 1 | |
HS Code | 2925190090 |
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Summary | 2925190090 other imides and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0% |