(R)-(+)-Thalidomide

Names

[ Name ]:
(R)-(+)-Thalidomide

[Synonym ]:
(+)-Thalidomide
MFCD00210220
(R)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione
(R)-(+)-Thalidomide
R-(+)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

Biological Activity

[Description]:

(R)-Thalidomide ((R)-(+)-Thalidomide) is the R-enantiomer of Thalidomide. (R)-Thalidomide has sedative properties[1][2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vitro]

The transport of the (R)-Thalidomide from the R-imprinted MIP-1 through the donor phase to the receiver phase is much less owing to the stronger retention of the thalidomide in the organic phase. With the affinity of (R)-Thalidomide by the MIP present surface capture, that is more strongly than the other forms. In the case of (R)-Thalidomide, it is found to bind to the selective sites of the MIP more strongly than the other which reflects their different biological entities[1]. The (S)-Thalidomide imprints MIP nanoparticles exerted a greater cytotoxic effect on the caco-2 cells than the (R)-Thalidomide imprinted MIPs[1].

[In Vivo]

Adult female F344 rats are implanted with 9L gliosarcoma tumours intracranially, subcutaneously (flank), or both. Effectiveness of oral thalidomide alone, and with intraperitoneal BCNU or cisplatin combination chemotherapy, is assessed after several weeks treatment. Both serum and tissue concentrations of (R)-thalidomide are 40-50% greater than those of (S)-thalidomide. Co-administration of BCNU or cisplatin with thalidomide did not alter the concentration enantioselectivity[1].

[References]

[1]. 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.

[2]. Eriksson T, et al. Intravenous formulations of the enantiomers of thalidomide: pharmacokinetic and initial pharmacodynamic characterization in man. J Pharm Pharmacol. 2000 Jul;52(7):807-17.

Chemical & Physical Properties

[ 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

[ Vapour Pressure ]:
1.65E-10mmHg at 25°C

[ Index of Refraction ]:
1.646

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TI4925000

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

CAS REGISTRY NUMBER :: 2614-06-4

LAST UPDATED :: 199012

DATA ITEMS CITED :: 4

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 :: 400 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 :: 50 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)

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

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H360

[ Precautionary Statements ]:
P201-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;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 ]:
S45;S53;S36/S37/S39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TI4925000

[ HS Code ]:
2925190090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ 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%

Articles

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...