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HomeProduct name listURB597

URB597

Synonym(s):Cyclohexylcarbamic acid 3′-carbamoyl-biphenyl-3-yl ester;FAAH Inhibitor II - CAS 546141-08-6 - Calbiochem;URB597, Cyclohexylcarbamic acid-3ʹ-carbamoyl-biphenyl-3-yl Ester, 3ʹ-Carbamoyl-biphenyl-3-yl-cyclohexylcarbamate

  • CAS NO.:546141-08-6
  • Empirical Formula: C20H22N2O3
  • Molecular Weight: 338.4
  • MDL number: MFCD05863934
  • EINECS: 637-274-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-01 18:09:03
URB597 Structural

What is URB597?

Description

URB-597 (546141-08-6) is a potent and selective fatty acid amide hydrolase (FAAH) inhibitor, IC50 = 3-5 nM.1?Produces cannabinoid CB1 and CB2 receptor-mediated analgesia in inflammatory pain states without causing side effects associated with cannabinoid receptor activation.2?Attenuates the anxiolytic-like effect of acetaminophen in a mouse model.3?Exerts anti-inflammatory effects in rat hippocampus and ameliorates age-related deficits.4?Off target effects of URB-597: Reduces tyrosine hydroxylase expression.5 Improves cognitive?impairment caused by chronic cerebral hypoperfusion in a mouse model via inhibition of mTOR-dependent autophagy.6

The Uses of URB597

URB597 is a potent, selective fatty acid amide hydrolase (FAAH) inhibitor.

What are the applications of Application

FAAH Inhibitor II is a cell permeable carbamate and potent inhibitor of fatty acid amide hydrolase (FAHH)

Definition

ChEBI: URB597 is a member of biphenyls.

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.

storage

Store at +4°C

References

1) Piomelli et al. (2006), Pharmacological profile of the selective FAAH inhibitor KDS-4103 (URB597); CNS Drugs Rev., 12 21 2) Jayamanne et al. (2006), Actions of the FAAH inhibitor URB597 in neuropathic and inflammatory chronic pain models; Br. J. Pharmacol., 147 281 3) Zaitone et al. (2012), Inhibition of fatty acid amide hydrolase by URB597 attenuates the anxiolytic-like effect of acetaminophen in the mouse elevated plus-maze test; Behav. Pharmacol., 23 417 4) Murphy et al. (2012), The fatty acid amide hydrolase inhibitor URB597 exerts anti-inflammatory effects in hippocampus of aged rats and restores an age-related deficit in long-term potentiation; Neuroinflammation, 9 79 5) Bosier et al. (2013), The FAAH inhibitor URB597 efficiently reduces tyrosine hydroxylase expression through CB- and FAAH-independent mechanisms; Br. J. Pharmacol., 169 794 6) Wang et al. (2017), URB597 improves cognitive impairment induced by chronic cerebral hypoperfusion by inhibiting mTOR-dependent autophagy; Neuroscience, 344 293

Properties of URB597

Boiling point: 533.2±50.0 °C(Predicted)
Density  1.23
storage temp.  2-8°C
solubility  DMSO: ~14 mg/mL, soluble
form  powder
pka 11.74±0.20(Predicted)
color  white
Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.

Safety information for URB597

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Environment
GHS09
GHS Hazard Statements H319:Serious eye damage/eye irritation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P273:Avoid release to the environment.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P501:Dispose of contents/container to..…

Computed Descriptors for URB597

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