URB597
URB597, also known as KDS-4103, is a potent and selective inhibitor of fatty-acid amide hydrolase (FAAH), an enzyme catalyzing the intracellular hydrolysis of the endocannabinoid anandamide, with values of 50% inhibition concentration IC50 of 5 nM and 3 nM in rat brain membranes and human liver microsomes respectively. Study results have shown that, through intraperitoneal (i.p.) administration, URB597 potently inhibits FAAH in rat brain with a median inhibitory dose ID50 of 0.15 mh/kg. However, URB597 fails to show significant inhibition against a few other cannabinoid-related targets (such as cannabinoid receptors and anandamide transport) as well as a broad range of receptors, ion channels, transporters and enymes.
Reference
Daniele Piomelli, Giorgio Tarzia, Andrea Duranti, Andrea Tontini, Marco Mor, Timothy R. Compton, Oliver Dasse, Edward P. Monaghan, Jeff A. Parrot and David Putman. Pharmacological profile of the selective FAAH inhibitor KDS-4103 (URB597). CNS Drug Review 2006; 12(1): 21-38
- 1. Milica Jankovic, Natasa Spasojevic, et al. "Sex specific effects of the fatty acid amide hydrolase inhibitor URB597 on memory and brain β2-adrenergic and D1-dopamine receptors." Neurosci Lett. 2021 Nov 27;768:136363. PMID: 34843876
- 2. Harisa Ferizovic, Natasa Spasojevic, et al. "Effects of Fatty Acid Amide Hydroxylase Inhibitor URB597 on the Catecholaminergic Activity of the Adrenal Medulla in Stressed Male and Female Rats." Pharmacology. 2021 Nov 18;1-9. PMID: 34794150
- 3. Milica Jankovic, Natasa Spasojevic, et al. "Inhibition of the fatty acid amide hydrolase changes behaviors and brain catecholamines in a sex-specific manner in rats exposed to chronic unpredictable stress." Physiol Behav. 2020 Dec 1;227:113174. PMID:32966816
- 4. Ferizovic H, Spasojevic N, et al. "The fatty acid amide hydrolase inhibitor URB597 modulates splenic catecholamines in chronically stressed female and male rats." Int Immunopharmacol. 2020;85:106615. PMID:32447219
| Storage | Store at -20°C |
| M.Wt | 338.4 |
| Cas No. | 546141-08-6 |
| Formula | C20H22N2O3 |
| Synonyms | FAAH Inhibitor II, URB-597, URB 597, KDS-4103 |
| Solubility | insoluble in H2O; ≥16.9 mg/mL in DMSO; ≥4.55 mg/mL in EtOH with gentle warming and ultrasonic |
| Chemical Name | [3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate |
| SDF | Download SDF |
| Canonical SMILES | C1CCC(CC1)NC(=O)OC2=CC=CC(=C2)C3=CC(=CC=C3)C(=O)N |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
Rat brain cortical neurons |
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Preparation method |
The solubility of this compound in DMSO is > 16.9 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
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Reacting condition |
10 nM |
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Applications |
URB597 selectively inhibited the breakdown of [3H]anandamide without reducing its carrier-mediated uptake, which caused non-metabolized [3H]anandamide to accumulate in, and finally exit from the cortical neurons. The accumulated [3H]anandamide was released from the neurons back into the media via passive diffusion rather than reverse transport. |
| Animal experiment [1]: | |
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Animal models |
Rats |
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Dosage form |
0.3 mg/kg; i.p. |
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Applications |
In rats, URB597 rapidly inhibited FAAH (< 15 mins) and its inhibitory effect could last for over 12 hrs. Meanwhile, the contents of anandamide and other fatty-acid ethanolamides were significantly elevated in brain. In addition, URB597 markedly enhanced the hypothermic response caused by a sub-threshold dose of anandamide (5 mg/kg; i.p.). However, when injected alone, URB597 showed no effect on body temperature. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Daniele Piomelli, Giorgio Tarzia, Andrea Duranti, Andrea Tontini, Marco Mor, Timothy R. Compton, Oliver Dasse, Edward P. Monaghan, Jeff A. Parrot and David Putman. Pharmacological profile of the selective FAAH inhibitor KDS-4103 (URB597). CNS Drug Review 2006; 12(1): 21-38. |
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| Description | URB597 is a potent and selective inhibitor of fatty acid amide hydrolase (FAAH) with IC50 values of 4.6 nM and 0.5 nM in brain membranes and intact neurons, respectively. | |||||
| Targets | FAAH | FAAH | ||||
| IC50 | 4.6 nM (brain membranes) | 0.5 nM (intact neurons) | ||||
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