(S)-Thalidomide

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Names

[ CAS No. ]:
841-67-8

[ Name ]:
(S)-Thalidomide

[Synonym ]:
(-)-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

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

[ Index of Refraction ]:
1.646

MSDS

Toxicological Information

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

Safety Information

[ 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

Synthetic Route

Precursor & DownStream

Precursor

  • 2H-Isoindole-2-aceticacid, a-(3-amino-3-oxopropyl)-1,3-dihydro-1,3-dioxo-,(aS)-
  • (S)-3-phthalimido-2-piperidinone
  • Thalidomide
  • N-Phthalyl isoglutamine
  • Phthalic anhydride
  • L-Glutamine
  • phthaloyl-l-glutamic anhydride
  • N-carbethoxyphthalimide

DownStream

  • (R)-(+)-Thalidomide

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...


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