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Merck
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Key Documents

SML0646

Sigma-Aldrich

GMX1778

≥98% (HPLC)

Synonyme(s) :

CHS 828, CHS-828, GMX 1778, N-[6-(4-Chlorophenoxy)hexyl]-N′-cyano-N′′-4-pyridinyl-guanidine

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About This Item

Formule empirique (notation de Hill):
C19H22ClN5O
Numéro CAS:
200484-11-3
Poids moléculaire :
371.86
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

−20°C

InChI

1S/C19H22ClN5O/c20-16-5-7-18(8-6-16)26-14-4-2-1-3-11-23-19(24-15-21)25-17-9-12-22-13-10-17/h5-10,12-13H,1-4,11,14H2,(H2,22,23,24,25)

Clé InChI

BOIPLTNGIAPDBY-UHFFFAOYSA-N

Application

GMX1778 has been used as NAMPT inhibitor, to study its effects on nicotinamide adenine dinucleotide (NAD) contents of SH-SY5Y cells exposed to Vacor.

Actions biochimiques/physiologiques

GMX1778 (CHS-828) is a competitive inhibitor of nicotinamide phosphoribosyltransferase (NAMPT) that exhibits a potent anticancer activity both in vitro and in vivo. GMX1778 exerts a cytotoxic effect by decreasing the cellular level of NAD+. GMX1778 increases intracellular ROS in cancer cells but does not induce ROS in normal cells.
GMX1778 can regulate redox status and has the ability to simulate ROS in cancer cells.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H315,H319,H335

Classification des risques

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

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

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

Identification of the nicotinamide salvage pathway as a new toxification route for antimetabolites
Buonvicino D, et al.
Cell Chemical Biology, 25(4), 471-482 (2018)
Inhibition of nicotinamide phosphoribosyltransferase (NAMPT) activity by small molecule GMX1778 regulates reactive oxygen species (ROS)-mediated cytotoxicity in a p53-and nicotinic acid phosphoribosyltransferase1 (NAPRT1)-dependent manner
Cerna D, et al.
The Journal of Biological Chemistry, 287(26), 22408-22417 (2012)
Daniela Buonvicino et al.
Cell chemical biology, 25(4), 471-482 (2018-02-27)
Interest in the modulation of nicotinamide adenine dinucleotide (NAD) metabolome is gaining great momentum because of its therapeutic potential in different human disorders. Suppression of nicotinamide salvage by nicotinamide phosphoribosyl transferase (NAMPT) inhibitors, however, gave inconclusive results in neoplastic patients because
Chiara Zucal et al.
BMC cancer, 15, 855-855 (2015-11-07)
Nicotinamide phosphoribosyltransferase (NAMPT), the rate-limiting enzyme in NAD(+) biosynthesis from nicotinamide, is one of the major factors regulating cancer cells metabolism and is considered a promising target for treating cancer. The prototypical NAMPT inhibitor FK866 effectively lowers NAD(+) levels in

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