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Merck

T151

Sigma-Aldrich

(+)-Thalidomide

≥98% (HPLC), powder

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C13H10N2O4
CAS-Nummer:
Molekulargewicht:
258.23
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:
NACRES:
NA.77

ligand

thalidomide

Assay

≥98% (HPLC)

Form

powder

Eignung der Reaktion

reagent type: ligand

Farbe

white to beige

Löslichkeit

DMSO: 15 mg/mL, clear

Ersteller

Celgene

Lagertemp.

room temp

SMILES String

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

InChIKey

UEJJHQNACJXSKW-SECBINFHSA-N

Angaben zum Gen

Anwendung

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.

Biochem./physiol. Wirkung

(-)-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.

Leistungsmerkmale und Vorteile

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

Angaben zur Herstellung

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.

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Piktogramme

Health hazardExclamation mark

Signalwort

Danger

H-Sätze

Gefahreneinstufungen

Acute Tox. 4 Oral - Repr. 1B

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
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 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
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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