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U4133

Sigma-Aldrich

URB597

≥98% (HPLC), powder

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Synonym(s):
Cyclohexylcarbamic acid 3´-carbamoyl-biphenyl-3-yl ester
Empirical Formula (Hill Notation):
C20H22N2O3
CAS Number:
Molecular Weight:
338.40
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: soluble ~14 mg/mL

storage temp.

2-8°C

SMILES string

NC(=O)c1cccc(c1)-c2cccc(OC(=O)NC3CCCCC3)c2

InChI

1S/C20H22N2O3/c21-19(23)16-8-4-6-14(12-16)15-7-5-11-18(13-15)25-20(24)22-17-9-2-1-3-10-17/h4-8,11-13,17H,1-3,9-10H2,(H2,21,23)(H,22,24)

InChI key

ROFVXGGUISEHAM-UHFFFAOYSA-N

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This Item
D4007G5045361563
vibrant-m

U4133

URB597

vibrant-m

D4007

5,5-Diphenylhydantoin

vibrant-m

G5045

GW6471

vibrant-m

361563

GSK-3 Inhibitor XXII, Compound A

assay

≥98% (HPLC)

assay

≥98%

assay

≥98% (HPLC)

assay

≥95% (HPLC)

form

powder

form

powder

form

powder

form

solid

color

white

color

-

color

white to beige

color

green-gray

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

solubility

DMSO: soluble ~14 mg/mL

solubility

DMSO: soluble

solubility

DMSO: 5 mg/mL, clear (warmed)

solubility

DMSO: 50 mg/mL

General description

URB597 binds to active sites of fatty acid amide hydrolases and inhibits their activity. URB597 alters expression of tyrosine hydroxylase and interacts with abnormal-cannabidiol (Abn-CBD) and peroxisome proliferator-activated receptors (PPARs). URB597 elicits antinociception property via cannabinoid receptor by maintaining endocannabinoid anandamide (AEA) levels. URB597 reduces abnormal hyperactivity in neurons and could be for treatment of seizures and improving synaptic plasticity.

Biochem/physiol Actions

Potent, selective fatty acid amide hydrolase (FAAH) inhibitor.

Preparation Note

URB597 is soluble in DMSO at a concentration that is approximately 14 mg/ml.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves


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The FAAH inhibitor URB597 efficiently reduces tyrosine hydroxylase expression through CB1-and FAAH-independent mechanisms
Bosier B, et al.
British Journal of Pharmacology, 169(4), 794-807 (2013)
Mechanism of carbamate inactivation of FAAH: implications for the design of covalent inhibitors and in vivo functional probes for enzymes
Alexander JP and Cravatt BF
Chemistry & Biology, 12(11), 1179-1187 (2005)
The FAAH inhibitor URB597 suppresses hippocampal maximal dentate afterdischarges and restores seizure-induced impairment of short and long-term synaptic plasticity
Colangeli R, et al.
Scientific Reports, 7(1), 11152-11152 (2017)
Interaction between the cholecystokinin and endogenous cannabinoid systems in cued fear expression and extinction retention
Bowers ME and Ressler KJ
Neuropsychopharmacology, 30, 688-688 (2015)
Luara A Batista et al.
Behavioural brain research, 317, 508-514 (2016-10-28)
Selective stimulation of carotid chemoreceptors by intravenous infusion of low doses of potassium cyanide (KCN) produces short-lasting escape responses that have been proposed as a model of panic attack. In turn, preclinical studies suggest that facilitation of the endocannabinoid system

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