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Key Documents

SML0646

Sigma-Aldrich

GMX1778

≥98% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C19H22ClN5O
CAS Number:
200484-11-3
Molecular Weight:
371.86
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

Clc1ccc(cc1)OCCCCCCN\C(=N\C#N)\Nc2ccncc2

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)

InChI key

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.

Biochem/physiol Actions

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.
GMX1778 is a competitive inhibitor of nicotinamide phosphoribosyltransferase (NAMPT).

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
036M4741V
033M4720V

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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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