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T151

Sigma-Aldrich

(+)-Thalidomide

≥98% (HPLC), powder

Synonyme(s) :

R-(+)-2-(2,6-Dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione

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About This Item

Formule empirique (notation de Hill):
C13H10N2O4
Numéro CAS:
2614-06-4
Poids moléculaire :
258.23
Numéro MDL:
MFCD00210220
Code UNSPSC :
12352200
ID de substance PubChem :
24899975
Nomenclature NACRES :
NA.77

ligand

thalidomide

Pureté

≥98% (HPLC)

Forme

powder

Pertinence de la réaction

reagent type: ligand

Couleur

white to beige

Solubilité

DMSO: 15 mg/mL, clear

Auteur

Celgene

Température de stockage

room temp

Chaîne SMILES 

O=C1CC[C@@H](N2C(=O)c3ccccc3C2=O)C(=O)N1

InChI

1S/C13H10N2O4/c16-10-6-5-9(11(17)14-10)15-12(18)7-3-1-2-4-8(7)13(15)19/h1-4,9H,5-6H2,(H,14,16,17)/t9-/m1/s1

Clé InChI

UEJJHQNACJXSKW-SECBINFHSA-N

Informations sur le gène

human ... LITAF(9516) , TNF(7124)
mouse ... Nos2(18126)
rat ... Nos1(24598)

Catégories apparentées

Application

Thalidomide has been used to study its teratogenic effects in chicken embryos and human embryonic cells. This study reported that thalidomide causes limb defects by stabilizing PTEN, inhibiting the expression of Akt and activating caspase-dependent apoptosis. Thalidomide has also been used for studying glutathione mediated teratogenic resistance in mouse embryos.

Actions biochimiques/physiologiques

(-)-Thalidomide selectively inhibits biosynthesis of tumor necrosis factor α (TNF-α). (R)-Thalidomide is called "safe enantiomer", but it can be converted in the body to (S)-isomer.

Caractéristiques et avantages

This compound was developed by Celgene. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Notes préparatoires

Thalidomide is soluble in DMSO at a concentration that is greater than or equal to 20 mg/ml. It is insoluble in ethanol and water.

Application

Réf. du produit
Description
Tarif

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

913979

Biotin-Thalidomide, ≥95%

924202

5-Amino-Thalidomide, ≥95%

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302,H360

Classification des risques

Acute Tox. 4 Oral - Repr. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Jianhui Zhao et al.
Neurochemical research, 41(12), 3171-3180 (2016-08-31)
Opioid analgesics have less efficacy in diabetic neuropathy treatment, and tolerance often occurs after chronic usage. Given that thalidomide can potentiate the morphine efficacy in diabetic neuropathy treatment, we investigated the effects of intrathecal administrations of thalidomide on morphine tolerance
Jürgen Knobloch et al.
Molecular and cellular biology, 28(2), 529-538 (2008-01-08)
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. Thalidomide-induced limb truncations result from increased cell death during embryonic limb
Agata Kowalczyk et al.
Biosensors & bioelectronics, 167, 112446-112446 (2020-08-21)
Fast, simple in use and highly effective voltammetric enantiosensor dedicated for determination of thalidomide (TD) enantiomers (especially towards the toxic (S)-enantiomer) in blood plasma is still desirable. Here we have proven that newly synthesized chiral naphthalene diimide (NDI) derivatives are
S Makonkawkeyoon et al.
Proceedings of the National Academy of Sciences of the United States of America, 90(13), 5974-5978 (1993-07-01)
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 inhibition is dose dependent and occurs after exposure of the cells to
Jürgen Knobloch et al.
Molecular pharmaceutics, 5(6), 1138-1144 (2009-05-13)
Thalidomide as an effective treatment for multiple myeloma and leprosy has also caused birth defects in thousands of children five decades ago particularly in Europe. Thus its use in humans remains limited. The rapid and fatal approval of thalidomide at
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