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A1987

Sigma-Aldrich

AM6545

≥98% (HPLC)

Synonym(s):

5-(4-[4-cyanobut-1-ynyl]phenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1,1-dioxo-thiomorpholino)-1H-pyrazole-3-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C26H23Cl2N5O3S
CAS Number:
1245626-05-4
Molecular Weight:
556.46
MDL number:
MFCD19053178
UNSPSC Code:
12352200
PubChem Substance ID:
329770727
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >25 mg/mL

storage temp.

2-8°C

SMILES string

Cc1c(nn(-c2ccc(Cl)cc2Cl)c1-c3ccc(cc3)C#CCCC#N)C(=O)NN4CCS(=O)(=O)CC4

InChI

1S/C26H23Cl2N5O3S/c1-18-24(26(34)31-32-13-15-37(35,36)16-14-32)30-33(23-11-10-21(27)17-22(23)28)25(18)20-8-6-19(7-9-20)5-3-2-4-12-29/h6-11,17H,2,4,13-16H2,1H3,(H,31,34)

InChI key

XBHQLFVDGLPBCK-UHFFFAOYSA-N

General description

AM6545 is a cannabinoid (CB1) receptor antagonist.

Biochem/physiol Actions

AM6545 helps in decreasing the development of albuminuria, inflammation and expression of markers of fibrosis. It also helps in the down-regulation of nephrin and podocin. It has the ability to repress the ingestion of food and food-reinforced behaviour.
AM6545 is a peripheral CB1 cannabinoid receptor antagonist and appetite suppressant.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jin Zhang et al.
Molecular medicine reports, 19(3), 1491-1500 (2018-12-21)
Increasing evidence suggests that the dysregulation of microRNAs (miRNAs) has an important role in the progression of human cancer, including ESCC. However, the exact functions and mechanisms of miRNAs in ESCC remain largely unclear. The aim of the present study
Reversal of albuminuria by combined AM6545 and perindopril therapy in experimental diabetic nephropathy
Barutta F, et al.
British Journal of Pharmacology, 175(23), 4371-4385 (2018)
Christian Montellese et al.
eLife, 9 (2020-03-05)
Establishment of translational competence represents a decisive cytoplasmic step in the biogenesis of 40S ribosomal subunits. This involves final 18S rRNA processing and release of residual biogenesis factors, including the protein kinase RIOK1. To identify novel proteins promoting the final
The novel cannabinoid CB1 antagonist AM6545 suppresses food intake and food-reinforced behavior
Randall PA, et al.
Pharmacol. Biochem., 97(1), 179-184 (2010)
Michael Ameismeier et al.
Nature, 587(7835), 683-687 (2020-11-20)
Eukaryotic ribosomes consist of a small 40S and a large 60S subunit that are assembled in a highly coordinated manner. More than 200 factors ensure correct modification, processing and folding of ribosomal RNA and the timely incorporation of ribosomal proteins1,2.
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