Description In vitro In vivo
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URB597

Description In vitro In vivo
Product Name
URB597
CAS No.
546141-08-6
Chemical Name
URB597
Synonyms
URB597;CS-115;KDS 4103;URB 597 NEW;URB597 powder;URB 597, >=98%;FAAH inhibitor;APD597(URB597);URB597 USP/EP/BP;FAAH INHIBITOR II
CBNumber
CB4331788
Molecular Formula
C20H22N2O3
Formula Weight
338.4
MOL File
546141-08-6.mol
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URB597 Property

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.
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Safety

Hazard Codes 
N
Risk Statements 
50/53
Safety Statements 
22-24/25-60-61
RIDADR 
UN 3077 9/PG 3
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
U4133
Product name
URB597
Purity
≥98% (HPLC)
Packaging
5mg
Price
$132
Updated
2024/03/01
Sigma-Aldrich
Product number
341249
Product name
FAAH Inhibitor II
Packaging
5mg
Price
$96.4
Updated
2023/01/07
Cayman Chemical
Product number
10046
Product name
URB597
Purity
>98%
Packaging
5mg
Price
$40
Updated
2024/03/01
Cayman Chemical
Product number
10046
Product name
URB597
Purity
>98%
Packaging
10mg
Price
$76
Updated
2024/03/01
Sigma-Aldrich
Product number
U4133
Product name
URB597
Purity
≥98% (HPLC), powder
Packaging
25mg
Price
$443
Updated
2024/03/01
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URB597 Chemical Properties,Usage,Production

Description

URB597 is a potent, orally bioavailable FAAH inhibitor with IC50 of 4.6 nM, with no activity on other cannabinoid-related targets. Phase 1.

In vitro

URB597 binds in the hydrophobic pocket and catalytic core of FAAH that connects the active site residues to the membrane surface of FAAH. URB597 inhibits FAAH activity in human liver microsomes with IC50 of 3 nM. URB597 reduces the expression of the LPS-induced enzymes cyclo-oxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS; NOS2) in primary rat microglial cell, with a concomitant reduction in the release of the inflammatory mediators prostaglandin E2 (PGE2) and (NO) nitric oxide. URB597 evokes Ca2+ entry in HEK293-F Cells transiently expressing human or rat TRPA1 gene. URB597 also activates Ca2+ entry in rat DRG neurons natively expressed TRPA1 channels.

In vivo

URB597 inhibits [3H]anandamide hydrolysis in rat brain membranes with a parallel increase in brain anandamide, OEA, and PEA content by inhibition of FAAH. URB597 enhances the hypothermia effect induced by ethanolamide by inhibiting FAAH.When delivered intraperitonealy (0.3 mg/kg) URB597 reduces allodynia and hyperalgesia through cannabinoid CB1 and CB2 receptor-mediated analgesia in rats with inflammatory pain.URB597 reduces the reduction in body weight gain and sucrose intake induced by the chronic mild stress in rats through inhibition of brain FAAH activity. URB597 could reverse most depressive-like symptoms induced by adolescent THC exposure in femal rats.

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

Uses

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

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

URB597 Preparation Products And Raw materials

Raw materials

Preparation Products

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URB597 Suppliers

SIGMA-RBI
Tel
--
Fax
--
Country
Switzerland
ProdList
6896
Advantage
91
Alexis Corporation
Tel
--
Fax
--
Email
alexis-ch@alexis-corp.ch
Country
Switzerland
ProdList
3599
Advantage
74
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View Lastest Price from URB597 manufacturers

Qiuxian Baitai New Material Co., LTD
Product
URB597 powder 546141-08-6
Price
US $18.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500ton/Month
Release date
2021-07-29
Career Henan Chemical Co
Product
URB597 546141-08-6
Price
US $2.00/KG
Min. Order
1g
Purity
98%min
Supply Ability
ask
Release date
2020-01-08

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