AM6545

CAT: 0804-HY-110206-02Size: 5 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-110206-02Size:5 mg

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Description

AM6545 is a highly selective, brain-free (peripherally active) CB1 receptor antagonist (Ki=1.7 nM) . AM6545 inhibits endocannabinoid signaling by competitively antagonizing CB1 receptors, inhibiting CB1-mediated appetite stimulation and inflammatory responses without affecting cAMP levels. AM6545 significantly reduces food intake and body weight in mice, while improving metabolic syndrome-related renal impairment (such as proteinuria, fibrosis) and insulin resistance. AM6545 can be used in the study of obesity and its complications[1][2][3].

CAS Number

1245626-05-4

UNSPSC

12352005

Hazard Statement

H319

Target

Cannabinoid Receptor

Type

Reference compound

Related Pathways

GPCR/G Protein; Neuronal Signaling

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/am6545.html

Concentration

10mM

Purity

99.32

Solubility

DMSO : ≥ 100 mg/mL

Smiles

CC1=C(C2=CC=C(C#CCCC#N)C=C2)N(C3=C(C=C(Cl)C=C3)Cl)N=C1C(NN4CCS(CC4)(=O)=O)=O

Molecular Formula

C26H23Cl2N5O3S

Molecular Weight

556.46

Precautions

H319

References & Citations

[1]N L Cluny, et al. A novel peripherally restricted cannabinoid receptor antagonist, AM6545, reduces food intake and body weight, but does not cause malaise, in rodents. Br J Pharmacol. 2010 Oct;161 (3) :629-42.|[2]Dalle S, Schouten M, Deboutte J, de Lange E, Ramaekers M, Koppo K. The molecular signature of the peripheral cannabinoid receptor 1 antagonist AM6545 in adipose, liver and muscle tissue. Toxicol Appl Pharmacol. 2024 Oct;491:117081.|[3]Eid BG, Neamatallah T, Hanafy A, El-Bassossy HM, Binmahfouz L, Aldawsari HM, Hasan A, El-Aziz GA, Vemuri K, Makriyannis A. Interference with TGFβ1-Mediated Inflammation and Fibrosis Underlies Reno-Protective Effects of the CB1 Receptor Neutral Antagonists AM6545 and AM4113 in a Rat Model of Metabolic Syndrome. Molecules. 2021 Feb 6;26 (4) :866. doi: 10.3390/molecules26040866. Erratum in: Molecules. 2024 Feb 19;29 (4) :902.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Chemical Information

AM6545

AM6545 is a member of the class of pyrazoles that is 1H-pyrazole substituted by 2,4-dichlorophenyl, N-(1,1-dioxidothiomorpholin-4-yl)aminoacyl, methyl, and 4-(4-cyanobut-1-yn-1-yl)phenyl groups at positions 1, 3, 4 and 5, respectively. It is a cannabinoid receptor 1 antagonist and a potential appetite suppressant. It has a role as an appetite depressant, a CB1 receptor antagonist and an anti-obesity agent. It is a nitrile, a dichlorobenzene, a member of pyrazoles, a carbohydrazide, a sulfone, a member of thiomorpholines and an arylacetylene.

CAS Number	1245626-05-4
PubChem CID	46912919
IUPAC Name	5-[4-(4-cyanobut-1-ynyl)phenyl]-1-(2,4-dichlorophenyl)-N-(1,1-dioxo-1,4-thiazinan-4-yl)-4-methylpyrazole-3-carboxamide
Molecular Formula	C26H23Cl2N5O3S
Molecular Weight	556.5
XLogP	4.5
Topological Polar Surface Area	116
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Heavy Atom Count	37
Formal Charge	0
Complexity	1020

SMILES

CC1=C(N(N=C1C(=O)NN2CCS(=O)(=O)CC2)C3=C(C=C(C=C3)Cl)Cl)C4=CC=C(C=C4)C#CCCC#N

InChI

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)

InChIKey

XBHQLFVDGLPBCK-UHFFFAOYSA-N

Chemical Structure

2D Structure

CAS: 1245626-05-4

CID: 46912919

Formula: C26H23Cl2N5O3S

MW: 556.5

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	556.5
XLogP3	4.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Exact Mass	555.0898662
Monoisotopic Mass	555.0898662
Topological Polar Surface Area	116 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	1020
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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C4711-10	AM6545

AM6545

Chemical Information

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