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SML0646

GMX1778

≥98% (HPLC), nicotinamide phosphoribosyltransferase (NAMPT) inhibitor, powder

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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Product Name

GMX1778, ≥98% (HPLC)

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 can regulate redox status and has the ability to simulate ROS in cancer cells.
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 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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000357480
0000357481
0000324186
0000324188
0000324188

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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
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Global Trade Item Number

SKUGTIN
SML0646-25MG04061833223413
SML0646-5MG04061833223420