(R)-(+)-Thalidomide

Modify Date: 2024-01-03 18:02:21

(R)-(+)-Thalidomide Structure
(R)-(+)-Thalidomide structure
Common Name (R)-(+)-Thalidomide
CAS Number 2614-06-4 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
GHS07, GHS08
Signal Word Danger

 Use of (R)-(+)-Thalidomide


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

 Names

Name (R)-thalidomide
Synonym More Synonyms

 (R)-(+)-Thalidomide Biological Activity

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

 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
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

 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%

 Articles4

More 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...

 Synonyms

(+)-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
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