(S)-Thalidomide

Modify Date: 2024-01-04 09:56:30

(S)-Thalidomide structure	Common Name	(S)-Thalidomide
	CAS Number	841-67-8	Molecular Weight	258.22900
	Density	1.503g/cm3	Boiling Point	509.7ºC at 760 mmHg
	Molecular Formula	C₁₃H₁₀N₂O₄	Melting Point	269-271ºC
	MSDS	Chinese USA	Flash Point	262.1ºC
	Symbol	GHS07, GHS08	Signal Word	Danger

Use of (S)-Thalidomide

(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].

Name	(S)-thalidomide
Synonym	More Synonyms

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].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Inflammation/Immunology Research Areas >> Metabolic Disease
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	[1]. Liu WM, et al. s-thalidomide has a greater effect on apoptosis than angiogenesis in a multiple myeloma cell line. Hematol J. 2004;5(3):247-54. [2]. Stephens TD. The effect of thalidomide in chicken embryos. Birth Defects Res A Clin Mol Teratol. 2009 Aug;85(8):725-31. [3]. Murphy S, et al. Enantioselectivity of thalidomide serum and tissue concentrations in a rat glioma model and effects of combination treatment with cisplatin and BCNU. J Pharm Pharmacol. 2007 Jan;59(1):105-14. [4]. Tokunaga E, et al. Understanding the Thalidomide Chirality in Biological Processes by the Self-disproportionation of Enantiomers. Sci Rep. 2018 Nov 20;8(1):17131.

Density	1.503g/cm3
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

(S)-Thalidomide MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TI4925050

CHEMICAL NAME :: Phthalimide, N-(2,6-dioxo-3-piperidyl)-, L-(-)-

CAS REGISTRY NUMBER :: 841-67-8

LAST UPDATED :: 199012

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C13-H10-N2-O4

MOLECULAR WEIGHT :: 258.25

WISWESSER LINE NOTATION :: T56 BVNVJ C- DT6VMVTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 215,296,1967 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 100 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1640,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 12500 ug/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1640,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 50 mg/kg

SEX/DURATION :: female 9 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 29,1640,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 900 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 215,296,1967 *** REVIEWS *** TOXICOLOGY REVIEW BCSTB5 Biochemical Society Transactions. (Biochemical Soc. Book Depot, POB 32, Commerce Way, Colchester, Essex CO2 8HP, UK) V.1- 1973- Volume(issue)/page/year: 2,695,1974

Symbol	GHS07, GHS08
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
CAS#:3343-29-1 2H-Isoindole-2-... CAS#:61071-65-6 (S)-3-phthalimi... CAS#:50-35-1 Thalidomide CAS#:2614-08-6 N-Phthalyl isog...
CAS#:85-44-9 Phthalic anhydride CAS#:56-85-9 L-Glutamine CAS#:25830-77-7 phthaloyl-l-glu... CAS#:22509-74-6 N-carbethoxypht...
DownStream 1
CAS#:2614-06-4 (R)-(+)-Thalidomide

HS Code	2925190090
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%

Thalidomide is an inhibitor of angiogenesis.

Proc. Natl. Acad. Sci. U. S. A. 91 , 4082, (1994)

Thalidomide is a potent teratogen causing dysmelia (stunted limb growth) in humans. We have demonstrated that orally administered thalidomide is an inhibitor of angiogenesis induced by basic fibroblas...

Thalidomide inhibits the replication of human immunodeficiency virus type 1.

Proc. Natl. Acad. Sci. U. S. A. 90 , 5974-5878, (1993)

Thalidomide, a selective inhibitor of tumor necrosis factor alpha (TNF-alpha) synthesis, suppresses the activation of latent human immunodeficiency virus type 1 (HIV-1) in a monocytoid (U1) line. The ...

Thalidomide induces limb anomalies by PTEN stabilization, Akt suppression, and stimulation of caspase-dependent cell death.

Mol. Cell. Biol. 28(2) , 529-538, (2008)

Thalidomide, a drug used for the treatment of multiple myeloma and inflammatory diseases, is also a teratogen that causes birth defects, such as limb truncations and microphthalmia, in humans. Thalido...

(-)-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

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China
Product Name: 1H-Isoindole-1,3(2H)-dione,2-[(3S)-2,6-dioxo-3-piperidinyl]-
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