URB602
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MedKoo CAT#: 530440

CAS#: 565460-15-3

Description: URB602 is a selective inhibitor of monoglycerol lipase (MGL), exhibiting an IC50 of 28 µM for the rat brain enzyme. Pretreatment with the monoacylglycerol lipase inhibitor URB602 protects from the long-term consequences of neonatal hypoxic-ischemic brain injury in rats. URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices.

Chemical Structure

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URB602
CAS# 565460-15-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 530440
Name: URB602
CAS#: 565460-15-3
Chemical Formula: C19H21NO2
Exact Mass: 295.16
Molecular Weight: 295.382
Elemental Analysis: C, 77.26; H, 7.17; N, 4.74; O, 10.83

Price and Availability

Size Price Availability Quantity
25mg USD 90 Ready to ship
50mg USD 150 Ready to ship
100mg USD 250 Ready to ship
200mg USD 450 Ready to ship
500mg USD 950 Ready to ship
1g USD 1710 Ready to ship
2g USD 3078 2 Weeks
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Synonym: URB602, URB-602, URB 602

IUPAC/Chemical Name: cyclohexyl [1,1'-biphenyl]-3-ylcarbamate

InChi Key: HHVUFQYJOSFTEH-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H21NO2/c21-19(22-18-12-5-2-6-13-18)20-17-11-7-10-16(14-17)15-8-3-1-4-9-15/h1,3-4,7-11,14,18H,2,5-6,12-13H2,(H,20,21)

SMILES Code: O=C(OC1CCCCC1)NC2=CC(C3=CC=CC=C3)=CC=C2

Appearance: White solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: URB602 is a selective monoacylglycerol lipase (MGL) inhibitor, which inhibits rat brain MGL with IC50 of 28±4 μM through a noncompetitive mechanism.
In vitro activity: Blockade of MGL activity with the pharmacological inhibitor URB602 led to increased [Ca(2+)](i )and enhanced insulin secretion from MIN6 β-cells, and MGL inhibition also elevated insulin and glucagon secretion from isolated human islets in vitro. Reference: Cell Physiol Biochem. 2012;30(2):347-58. https://pubmed.ncbi.nlm.nih.gov/22739267/
In vivo activity: These experiments revealed a significant reduction of brain injury in rats when URB602 was administered at doses of 12.5 μg and 25 μg (Figure 1a,b) into the right ventricle, ipsilateral to the occluded carotid, or when a dose of 50 μg was injected into the left ventricle, contralateral to the occluded carotid (Figure 1c). Reference: Pediatr Res. 2012 Oct;72(4):400-6. https://pubmed.ncbi.nlm.nih.gov/22821058/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 101.56
DMSO 63.0 213.28
DMSO:PBS (pH 7.2) (1:1) 0.3 0.85
Ethanol 34.5 116.80

Preparing Stock Solutions

The following data is based on the product molecular weight 295.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Li C, Vilches-Flores A, Zhao M, Amiel SA, Jones PM, Persaud SJ. Expression and function of monoacylglycerol lipase in mouse β-cells and human islets of Langerhans. Cell Physiol Biochem. 2012;30(2):347-58. doi: 10.1159/000339069. Epub 2012 Jun 26. PMID: 22739267. 2. Carloni S, Alonso-Alconada D, Girelli S, Duranti A, Tontini A, Piomelli D, Hilario E, Alvarez A, Balduini W. Pretreatment with the monoacylglycerol lipase inhibitor URB602 protects from the long-term consequences of neonatal hypoxic-ischemic brain injury in rats. Pediatr Res. 2012 Oct;72(4):400-6. doi: 10.1038/pr.2012.91. Epub 2012 Jul 20. PMID: 22821058. 3. King AR, Duranti A, Tontini A, Rivara S, Rosengarth A, Clapper JR, Astarita G, Geaga JA, Luecke H, Mor M, Tarzia G, Piomelli D. URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices. Chem Biol. 2007 Dec;14(12):1357-65. doi: 10.1016/j.chembiol.2007.10.017. PMID: 18096504; PMCID: PMC2225625.
In vitro protocol: 1. Li C, Vilches-Flores A, Zhao M, Amiel SA, Jones PM, Persaud SJ. Expression and function of monoacylglycerol lipase in mouse β-cells and human islets of Langerhans. Cell Physiol Biochem. 2012;30(2):347-58. doi: 10.1159/000339069. Epub 2012 Jun 26. PMID: 22739267.
In vivo protocol: 1. Carloni S, Alonso-Alconada D, Girelli S, Duranti A, Tontini A, Piomelli D, Hilario E, Alvarez A, Balduini W. Pretreatment with the monoacylglycerol lipase inhibitor URB602 protects from the long-term consequences of neonatal hypoxic-ischemic brain injury in rats. Pediatr Res. 2012 Oct;72(4):400-6. doi: 10.1038/pr.2012.91. Epub 2012 Jul 20. PMID: 22821058. 2. King AR, Duranti A, Tontini A, Rivara S, Rosengarth A, Clapper JR, Astarita G, Geaga JA, Luecke H, Mor M, Tarzia G, Piomelli D. URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices. Chem Biol. 2007 Dec;14(12):1357-65. doi: 10.1016/j.chembiol.2007.10.017. PMID: 18096504; PMCID: PMC2225625.

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1: Carloni S, Alonso-Alconada D, Girelli S, Duranti A, Tontini A, Piomelli D, Hilario E, Alvarez A, Balduini W. Pretreatment with the monoacylglycerol lipase inhibitor URB602 protects from the long-term consequences of neonatal hypoxic-ischemic brain injury in rats. Pediatr Res. 2012 Oct;72(4):400-6. doi: 10.1038/pr.2012.91. PubMed PMID: 22821058.

2: Szabo M, Agostino M, Malone DT, Yuriev E, Capuano B. The design, synthesis and biological evaluation of novel URB602 analogues as potential monoacylglycerol lipase inhibitors. Bioorg Med Chem Lett. 2011 Nov 15;21(22):6782-7. doi: 10.1016/j.bmcl.2011.09.038. PubMed PMID: 21982493.

3: Comelli F, Giagnoni G, Bettoni I, Colleoni M, Costa B. The inhibition of monoacylglycerol lipase by URB602 showed an anti-inflammatory and anti-nociceptive effect in a murine model of acute inflammation. Br J Pharmacol. 2007 Nov;152(5):787-94. PubMed PMID: 17700715; PubMed Central PMCID: PMC2190015.

4: King AR, Duranti A, Tontini A, Rivara S, Rosengarth A, Clapper JR, Astarita G, Geaga JA, Luecke H, Mor M, Tarzia G, Piomelli D. URB602 inhibits monoacylglycerol lipase and selectively blocks 2-arachidonoylglycerol degradation in intact brain slices. Chem Biol. 2007 Dec;14(12):1357-65. PubMed PMID: 18096504; PubMed Central PMCID: PMC2225625.

5: Vandevoorde S, Jonsson KO, Labar G, Persson E, Lambert DM, Fowler CJ. Lack of selectivity of URB602 for 2-oleoylglycerol compared to anandamide hydrolysis in vitro. Br J Pharmacol. 2007 Jan;150(2):186-91. PubMed PMID: 17143303; PubMed Central PMCID: PMC2042901.

6: Guindon J, Guijarro A, Piomelli D, Hohmann AG. Peripheral antinociceptive effects of inhibitors of monoacylglycerol lipase in a rat model of inflammatory pain. Br J Pharmacol. 2011 Aug;163(7):1464-78. doi: 10.1111/j.1476-5381.2010.01192.x. PubMed PMID: 21198549; PubMed Central PMCID: PMC3165956.

7: Dong M, Lu Y, Zou Z, Yang H. Monoacylglycerol lipase inhibitor protects primary cultured neurons against homocysteine-induced impairments in rat caudate nucleus through COX-2 signaling. Life Sci. 2015 Oct 1;138:64-71. doi: 10.1016/j.lfs.2015.03.006. PubMed PMID: 25818189.

8: Almeida-Santos AF, Gobira PH, Rosa LC, Guimaraes FS, Moreira FA, Aguiar DC. Modulation of anxiety-like behavior by the endocannabinoid 2-arachidonoylglycerol (2-AG) in the dorsolateral periaqueductal gray. Behav Brain Res. 2013 Sep 1;252:10-7. doi: 10.1016/j.bbr.2013.05.027. PubMed PMID: 23714073.

9: Guindon J, Desroches J, Beaulieu P. The antinociceptive effects of intraplantar injections of 2-arachidonoyl glycerol are mediated by cannabinoid CB2 receptors. Br J Pharmacol. 2007 Mar;150(6):693-701. PubMed PMID: 17179944; PubMed Central PMCID: PMC2013873.

10: Gobira PH, Almeida-Santos AF, Guimaraes FS, Moreira FA, Aguiar DC. Role of the endocannabinoid 2-arachidonoylglycerol in aversive responses mediated by the dorsolateral periaqueductal grey. Eur Neuropsychopharmacol. 2016 Jan;26(1):15-22. doi: 10.1016/j.euroneuro.2015.11.014. PubMed PMID: 26628106.

11: Desroches J, Charron S, Bouchard JF, Beaulieu P. Endocannabinoids decrease neuropathic pain-related behavior in mice through the activation of one or both peripheral CB₁ and CB₂ receptors. Neuropharmacology. 2014 Feb;77:441-52. doi: 10.1016/j.neuropharm.2013.10.006. PubMed PMID: 24148808.

12: Wright LK, Liu J, Nallapaneni A, Pope CN. Behavioral sequelae following acute diisopropylfluorophosphate intoxication in rats: comparative effects of atropine and cannabinomimetics. Neurotoxicol Teratol. 2010 May-Jun;32(3):329-35. doi: 10.1016/j.ntt.2009.12.006. PubMed PMID: 20034559; PubMed Central PMCID: PMC2854260.

13: Naderi N, Ahmad-Molaei L, Aziz Ahari F, Motamedi F. Modulation of anticonvulsant effects of cannabinoid compounds by GABA-A receptor agonist in acute pentylenetetrazole model of seizure in rat. Neurochem Res. 2011 Aug;36(8):1520-5. doi: 10.1007/s11064-011-0479-1. PubMed PMID: 21516342.

14: Berdan CA, Erion KA, Burritt NE, Corkey BE, Deeney JT. Inhibition of Monoacylglycerol Lipase Activity Decreases Glucose-Stimulated Insulin Secretion in INS-1 (832/13) Cells and Rat Islets. PLoS One. 2016 Feb 11;11(2):e0149008. doi: 10.1371/journal.pone.0149008. PubMed PMID: 26867016; PubMed Central PMCID: PMC4750965.

15: Desroches J, Guindon J, Lambert C, Beaulieu P. Modulation of the anti-nociceptive effects of 2-arachidonoyl glycerol by peripherally administered FAAH and MGL inhibitors in a neuropathic pain model. Br J Pharmacol. 2008 Nov;155(6):913-24. doi: 10.1038/bjp.2008.322. PubMed PMID: 18695638; PubMed Central PMCID: PMC2597245.

16: Li C, Vilches-Flores A, Zhao M, Amiel SA, Jones PM, Persaud SJ. Expression and function of monoacylglycerol lipase in mouse β-cells and human islets of Langerhans. Cell Physiol Biochem. 2012;30(2):347-58. doi: 10.1159/000339069. PubMed PMID: 22739267.

17: Du H, Chen X, Zhang J, Chen C. Inhibition of COX-2 expression by endocannabinoid 2-arachidonoylglycerol is mediated via PPAR-γ. Br J Pharmacol. 2011 Aug;163(7):1533-49. doi: 10.1111/j.1476-5381.2011.01444.x. PubMed PMID: 21501147; PubMed Central PMCID: PMC3165961.

18: Ho YC, Lee HJ, Tung LW, Liao YY, Fu SY, Teng SF, Liao HT, Mackie K, Chiou LC. Activation of orexin 1 receptors in the periaqueductal gray of male rats leads to antinociception via retrograde endocannabinoid (2-arachidonoylglycerol)-induced disinhibition. J Neurosci. 2011 Oct 12;31(41):14600-10. doi: 10.1523/JNEUROSCI.2671-11.2011. PubMed PMID: 21994376; PubMed Central PMCID: PMC3265563.

19: Chen X, Zhang J, Chen C. Endocannabinoid 2-arachidonoylglycerol protects neurons against β-amyloid insults. Neuroscience. 2011 Mar 31;178:159-68. doi: 10.1016/j.neuroscience.2011.01.024. PubMed PMID: 21256197; PubMed Central PMCID: PMC3052737.

20: García Mdel C, Adler-Graschinsky E, Celuch SM. Enhancement of the hypotensive effects of intrathecally injected endocannabinoids by the entourage compound palmitoylethanolamide. Eur J Pharmacol. 2009 May 21;610(1-3):75-80. doi: 10.1016/j.ejphar.2009.03.021. PubMed PMID: 19289116.