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MedKoo Cat#: 530440 | Name: URB602
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

URB602
URB602
CAS#565460-15-3

Theoretical Analysis

MedKoo Cat#: 530440

Name: URB602

CAS#: 565460-15-3

Chemical Formula: C19H21NO2

Exact Mass: 295.1572

Molecular Weight: 295.38

Elemental Analysis: C, 77.26; H, 7.17; N, 4.74; O, 10.83

Price and Availability

Size Price Availability Quantity
25mg USD 90.00 Ready to ship
50mg USD 150.00 Ready to ship
100mg USD 250.00 Ready to ship
200mg USD 450.00 Ready to ship
500mg USD 950.00 Ready to ship
1g USD 1,710.00 Ready to ship
2g USD 3,078.00 2 Weeks
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Related CAS #
No Data
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/
Solvent mg/mL 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
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Mitra S, Gobira PH, Werner CT, Martin JA, Iida M, Thomas SA, Erias K, Miracle S, Lafargue C, An C, Dietz DM. A role for the endocannabinoid enzymes monoacylglycerol and diacylglycerol lipases in cue-induced cocaine craving following prolonged abstinence. Addict Biol. 2021 Sep;26(5):e13007. doi: 10.1111/adb.13007. Epub 2021 Jan 25. PMID: 33496035; PMCID: PMC11000690. 2: Pavon FJ, Polis I, Stouffer DG, Roberto M, Martin-Fardon R, Rodriguez de Fonseca F, Parsons LH, Serrano A. COX-2 Inhibition Antagonizes Intra-Accumbens 2-Arachidonoylglycerol-Mediated Reduction in Ethanol Self-Administration in Rats. Alcohol Clin Exp Res. 2020 Nov;44(11):2158-2165. doi: 10.1111/acer.14456. Epub 2020 Oct 3. PMID: 32944989; PMCID: PMC7680444. 3: Orrego-González E, Londoño-Tobón L, Ardila-González J, Polania-Tovar D, Valencia-Cárdenas A, Velez-Van Meerbeke A. Cannabinoid Effects on Experimental Colorectal Cancer Models Reduce Aberrant Crypt Foci (ACF) and Tumor Volume: A Systematic Review. Evid Based Complement Alternat Med. 2020 Jul 20;2020:2371527. doi: 10.1155/2020/2371527. PMID: 32765628; PMCID: PMC7387981. 4: Gerace E, Zianni E, Landucci E, Scartabelli T, Berlinguer Palmini R, Iezzi D, Moroni F, Di Luca M, Mannaioni G, Gardoni F, Pellegrini-Giampietro DE. Differential mechanisms of tolerance induced by NMDA and 3,5-dihydroxyphenylglycine (DHPG) preconditioning. J Neurochem. 2020 Dec;155(6):638-649. doi: 10.1111/jnc.15033. Epub 2020 May 18. PMID: 32343420. 5: Li XH, Liu YQ, Gong DY, Hai KR, Ke BW, Zuo YX. The Critical Role of Cannabinoid Receptor 2 in URB602-Induced Protective Effects Against Renal Ischemia-Reperfusion Injury in the Rat. Shock. 2020 Oct;54(4):520-530. doi: 10.1097/SHK.0000000000001517. PMID: 32004183. 6: Miceli M, Casati S, Ottria R, Di Leo S, Eberini I, Palazzolo L, Parravicini C, Ciuffreda P. Set-Up and Validation of a High Throughput Screening Method for Human Monoacylglycerol Lipase (MAGL) Based on a New Red Fluorescent Probe. Molecules. 2019 Jun 15;24(12):2241. doi: 10.3390/molecules24122241. PMID: 31208066; PMCID: PMC6631453. 7: Monoacylglycerol Lipase Inactivation by Using URB602 Mitigates Myocardial Damage in a Rat Model of Cardiac Arrest: Erratum. Crit Care Med. 2019 Jun;47(6):e537. doi: 10.1097/CCM.0000000000003749. Erratum for: Crit Care Med. 2019 Feb;47(2):e144-e151. doi: 10.1097/CCM.0000000000003552. PMID: 31095034. 8: Freitas HR, Isaac AR, Silva TM, Diniz GOF, Dos Santos Dabdab Y, Bockmann EC, Guimarães MZP, da Costa Calaza K, de Mello FG, Ventura ALM, de Melo Reis RA, França GR. Cannabinoids Induce Cell Death and Promote P2X7 Receptor Signaling in Retinal Glial Progenitors in Culture. Mol Neurobiol. 2019 Sep;56(9):6472-6486. doi: 10.1007/s12035-019-1537-y. Epub 2019 Mar 5. PMID: 30838518. 9: Viana TG, Bastos JR, Costa RB, Hott SC, Mansur FS, Coimbra CC, Resstel LB, Aguiar DC, Moreira FA. Hypothalamic endocannabinoid signalling modulates aversive responses related to panic attacks. Neuropharmacology. 2019 Apr;148:284-290. doi: 10.1016/j.neuropharm.2019.01.022. Epub 2019 Jan 21. PMID: 30677422. 10: Hai K, Chen G, Gou X, Jiang H, Gong D, Cheng Y, Gong C, Li X, Liu Y, Li H, Zhang G, Yang L, Ke B, Liu J. Monoacylglycerol Lipase Inactivation by Using URB602 Mitigates Myocardial Damage in a Rat Model of Cardiac Arrest. Crit Care Med. 2019 Feb;47(2):e144-e151. doi: 10.1097/CCM.0000000000003552. Erratum in: Crit Care Med. 2019 Jun;47(6):e537. doi: 10.1097/CCM.0000000000003749. Jang, Haixia [corrected to Jiang, Haixia] and Gong, Chansheng [corrected to Gong, Cansheng]. PMID: 30431495. 11: Xiong Y, Yao H, Cheng Y, Gong D, Liao X, Wang R. Effects of monoacylglycerol lipase inhibitor URB602 on lung ischemia-reperfusion injury in mice. Biochem Biophys Res Commun. 2018 Nov 30;506(3):578-584. doi: 10.1016/j.bbrc.2018.10.098. Epub 2018 Oct 23. PMID: 30366666. 12: Lauria S, Perrotta C, Casati S, Di Renzo I, Ottria R, Eberini I, Palazzolo L, Parravicini C, Ciuffreda P. Design, synthesis, molecular modelling and in vitro cytotoxicity analysis of novel carbamate derivatives as inhibitors of Monoacylglycerol lipase. Bioorg Med Chem. 2018 May 15;26(9):2561-2572. doi: 10.1016/j.bmc.2018.04.024. Epub 2018 Apr 12. PMID: 29678535. 13: McReynolds JR, Doncheck EM, Li Y, Vranjkovic O, Graf EN, Ogasawara D, Cravatt BF, Baker DA, Liu QS, Hillard CJ, Mantsch JR. Stress Promotes Drug Seeking Through Glucocorticoid-Dependent Endocannabinoid Mobilization in the Prelimbic Cortex. Biol Psychiatry. 2018 Jul 15;84(2):85-94. doi: 10.1016/j.biopsych.2017.09.024. Epub 2017 Oct 6. PMID: 29100630; PMCID: PMC5889367. 14: Greco R, Demartini C, Zanaboni AM, Berliocchi L, Piomelli D, Tassorelli C. Inhibition of monoacylglycerol lipase: Another signalling pathway for potential therapeutic targets in migraine? Cephalalgia. 2018 May;38(6):1138-1147. doi: 10.1177/0333102417727537. Epub 2017 Aug 17. PMID: 28816506. 15: Almeida-Santos AF, Moreira FA, Guimaraes FS, Aguiar DC. 2-Arachidonoylglycerol endocannabinoid signaling coupled to metabotropic glutamate receptor type-5 modulates anxiety-like behavior in the rat ventromedial prefrontal cortex. J Psychopharmacol. 2017 Jun;31(6):740-749. doi: 10.1177/0269881117704986. Epub 2017 Apr 25. PMID: 28440729. 16: Pagano E, Borrelli F, Orlando P, Romano B, Monti M, Morbidelli L, Aviello G, Imperatore R, Capasso R, Piscitelli F, Buono L, Di Marzo V, Izzo AA. Pharmacological inhibition of MAGL attenuates experimental colon carcinogenesis. Pharmacol Res. 2017 May;119:227-236. doi: 10.1016/j.phrs.2017.02.002. Epub 2017 Feb 11. PMID: 28193521. 17: Araki M, Ohshima N, Aso C, Konishi A, Obinata H, Tatei K, Izumi T. Enzymatic characterization of recombinant rat DDHD2: a soluble diacylglycerol lipase. J Biochem. 2016 Nov;160(5):269-279. doi: 10.1093/jb/mvw034. Epub 2016 May 19. PMID: 27198176. 18: 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. PMID: 26867016; PMCID: PMC4750965. 19: 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. Epub 2015 Nov 25. PMID: 26628106. 20: Lauria S, Casati S, Ciuffreda P. Synthesis and characterization of a new fluorogenic substrate for monoacylglycerol lipase and application to inhibition studies. Anal Bioanal Chem. 2015 Oct;407(26):8163-7. doi: 10.1007/s00216-015-8991-9. Epub 2015 Sep 2. PMID: 26329281.