URB597 (KDS-4103)
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Hodoodo CAT#: H522479

CAS#: 546141-08-6

Description: URB597, also known as KDS-4103, is a relatively selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH). FAAH is the primary degradatory enzyme for the endocannabinoid anandamide and, as such, inhibition of FAAH leads to an accumulation of anandamide in the CNS and periphery where it activates cannabinoid receptors. In pre-clinical laboratory tests researchers found URB597 increased the production of endocannabinoids resulting in measurable antidepressant and analgesic effects.

Chemical Structure

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URB597 (KDS-4103)
CAS# 546141-08-6
Instruction

Theoretical Analysis

Hodoodo Cat#: H522479
Name: URB597 (KDS-4103)
CAS#: 546141-08-6
Chemical Formula: C20H22N2O3
Exact Mass: 338.16
Molecular Weight: 338.407
Elemental Analysis: C, 70.99; H, 6.55; N, 8.28; O, 14.18

Price and Availability

Size Price Availability Quantity
10mg USD 250 2 Weeks
25mg USD 450 2 Weeks
50mg USD 750 2 Weeks
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Synonym: URB597, URB-597, URB 597, KDS-4103, KDS4103, KDS 4103

IUPAC/Chemical Name: [3-(3-carbamoylphenyl)phenyl] N-cyclohexylcarbamate

InChi Key: ROFVXGGUISEHAM-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H22N2O3/c21-19(23)16-8-4-6-14(12-16)15-7-5-11-18(13-15)25-20(24)22-17-9-2-1-3-10-17/h4-8,11-13,17H,1-3,9-10H2,(H2,21,23)(H,22,24)

SMILES Code: O=C(OC1=CC=CC(C2=CC=CC(C(N)=O)=C2)=C1)NC3CCCCC3

Appearance: White to off-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, not in water

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:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 338.41 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:
In vitro protocol:
In vivo protocol:

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1: Hasanein P, Ghafari-Vahed M. Fatty acid amide hydrolase inhibitor URB597 prevented tolerance and cognitive deficits induced by chronic morphine administration in rats. Behav Pharmacol. 2015 Aug 25. [Epub ahead of print] PubMed PMID: 26274041.

2: Su SH, Wu YF, Lin Q, Yu F, Hai J. Cannabinoid receptor agonist WIN55,212-2 and fatty acid amide hydrolase inhibitor URB597 suppress chronic cerebral hypoperfusion-induced neuronal apoptosis by inhibiting c-Jun N-terminal kinase signaling. Neuroscience. 2015 Aug 20;301:563-75. doi: 10.1016/j.neuroscience.2015.03.021. Epub 2015 Mar 18. PubMed PMID: 25795598.

3: Hasanein P, Teimuri Far M. Effects of URB597 as an inhibitor of fatty acid amide hydrolase on WIN55, 212-2-induced learning and memory deficits in rats. Pharmacol Biochem Behav. 2015 Apr;131:130-5. doi: 10.1016/j.pbb.2015.02.007. Epub 2015 Feb 15. PubMed PMID: 25689415.

4: Bedse G, Colangeli R, Lavecchia AM, Romano A, Altieri F, Cifani C, Cassano T, Gaetani S. Role of the basolateral amygdala in mediating the effects of the fatty acid amide hydrolase inhibitor URB597 on HPA axis response to stress. Eur Neuropsychopharmacol. 2014 Sep;24(9):1511-23. doi: 10.1016/j.euroneuro.2014.07.005. Epub 2014 Jul 19. PubMed PMID: 25106694.

5: Manduca A, Servadio M, Campolongo P, Palmery M, Trabace L, Vanderschuren LJ, Cuomo V, Trezza V. Strain- and context-dependent effects of the anandamide hydrolysis inhibitor URB597 on social behavior in rats. Eur Neuropsychopharmacol. 2014 Aug;24(8):1337-48. doi: 10.1016/j.euroneuro.2014.05.009. Epub 2014 May 20. PubMed PMID: 24933531.

6: Kwilasz AJ, Abdullah RA, Poklis JL, Lichtman AH, Negus SS. Effects of the fatty acid amide hydrolase inhibitor URB597 on pain-stimulated and pain-depressed behavior in rats. Behav Pharmacol. 2014 Apr;25(2):119-29. doi: 10.1097/FBP.0000000000000023. PubMed PMID: 24583930; PubMed Central PMCID: PMC3963812.

7: Ceci C, Mela V, Macrì S, Marco EM, Viveros MP, Laviola G. Prenatal corticosterone and adolescent URB597 administration modulate emotionality and CB1 receptor expression in mice. Psychopharmacology (Berl). 2014 May;231(10):2131-44. doi: 10.1007/s00213-013-3367-3. Epub 2013 Dec 6. PubMed PMID: 24311359.

8: Haller J, Aliczki M, Pelczer KG, Spitzer K, Balogh Z, Kantor S. Effects of the fatty acid amide hydrolase inhibitor URB597 on coping behavior under challenging conditions in mice. Psychopharmacology (Berl). 2014 Feb;231(3):593-601. doi: 10.1007/s00213-013-3273-8. Epub 2013 Sep 14. PubMed PMID: 24037493.

9: Haller J, Goldberg SR, Pelczer KG, Aliczki M, Panlilio LV. The effects of anandamide signaling enhanced by the FAAH inhibitor URB597 on coping styles in rats. Psychopharmacology (Berl). 2013 Dec;230(3):353-62. doi: 10.1007/s00213-013-3161-2. Epub 2013 Jun 7. PubMed PMID: 23743650; PubMed Central PMCID: PMC3830591.

10: Slusar JE, Cairns EA, Szczesniak AM, Bradshaw HB, Di Polo A, Kelly ME. The fatty acid amide hydrolase inhibitor, URB597, promotes retinal ganglion cell neuroprotection in a rat model of optic nerve axotomy. Neuropharmacology. 2013 Sep;72:116-25. doi: 10.1016/j.neuropharm.2013.04.018. Epub 2013 May 3. PubMed PMID: 23643752.

11: Bosier B, Muccioli GG, Lambert DM. The FAAH inhibitor URB597 efficiently reduces tyrosine hydroxylase expression through CB₁- and FAAH-independent mechanisms. Br J Pharmacol. 2013 Jun;169(4):794-807. doi: 10.1111/j.1476-5381.2012.02208.x. PubMed PMID: 22970888; PubMed Central PMCID: PMC3687660.

12: Crow JA, Bittles V, Borazjani A, Potter PM, Ross MK. Covalent inhibition of recombinant human carboxylesterase 1 and 2 and monoacylglycerol lipase by the carbamates JZL184 and URB597. Biochem Pharmacol. 2012 Nov 1;84(9):1215-22. doi: 10.1016/j.bcp.2012.08.017. Epub 2012 Aug 27. PubMed PMID: 22943979; PubMed Central PMCID: PMC3470872.

13: Zaitone SA, El-Wakeil AF, Abou-El-Ela SH. Inhibition of fatty acid amide hydrolase by URB597 attenuates the anxiolytic-like effect of acetaminophen in the mouse elevated plus-maze test. Behav Pharmacol. 2012 Aug;23(4):417-25. doi: 10.1097/FBP.0b013e3283566065. PubMed PMID: 22750843.

14: Okine BN, Norris LM, Woodhams S, Burston J, Patel A, Alexander SP, Barrett DA, Kendall DA, Bennett AJ, Chapman V. Lack of effect of chronic pre-treatment with the FAAH inhibitor URB597 on inflammatory pain behaviour: evidence for plastic changes in the endocannabinoid system. Br J Pharmacol. 2012 Oct;167(3):627-40. doi: 10.1111/j.1476-5381.2012.02028.x. PubMed PMID: 22595021; PubMed Central PMCID: PMC3449266.

15: Murphy N, Cowley TR, Blau CW, Dempsey CN, Noonan J, Gowran A, Tanveer R, Olango WM, Finn DP, Campbell VA, Lynch MA. 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. J Neuroinflammation. 2012 Apr 26;9:79. doi: 10.1186/1742-2094-9-79. PubMed PMID: 22537429; PubMed Central PMCID: PMC3409037.

16: Hamtiaux L, Masquelier J, Muccioli GG, Bouzin C, Feron O, Gallez B, Lambert DM. The association of N-palmitoylethanolamine with the FAAH inhibitor URB597 impairs melanoma growth through a supra-additive action. BMC Cancer. 2012 Mar 19;12:92. doi: 10.1186/1471-2407-12-92. PubMed PMID: 22429826; PubMed Central PMCID: PMC3364151.

17: Murillo-Rodríguez E, Palomero-Rivero M, Millán-Aldaco D, Arias-Carrión O, Drucker-Colín R. Administration of URB597, oleoylethanolamide or palmitoylethanolamide increases waking and dopamine in rats. PLoS One. 2011;6(7):e20766. doi: 10.1371/journal.pone.0020766. Epub 2011 Jul 14. PubMed PMID: 21779318; PubMed Central PMCID: PMC3136458.

18: Schuelert N, Johnson MP, Oskins JL, Jassal K, Chambers MG, McDougall JJ. Local application of the endocannabinoid hydrolysis inhibitor URB597 reduces nociception in spontaneous and chemically induced models of osteoarthritis. Pain. 2011 May;152(5):975-81. doi: 10.1016/j.pain.2010.11.025. Epub 2010 Dec 24. PubMed PMID: 21185649.

19: Realini N, Vigano' D, Guidali C, Zamberletti E, Rubino T, Parolaro D. Chronic URB597 treatment at adulthood reverted most depressive-like symptoms induced by adolescent exposure to THC in female rats. Neuropharmacology. 2011 Feb-Mar;60(2-3):235-43. doi: 10.1016/j.neuropharm.2010.09.003. Epub 2010 Sep 17. PubMed PMID: 20850463.

20: Soukupová M, Palazzo E, De Chiaro M, Gatta L, Migliozzi AL, Guida F, Luongo L, Giordano C, Siniscalco D, De Novellis V, Marabese I, Krsiak M, Maione S. Effects of URB597, an inhibitor of fatty acid amide hydrolase (FAAH), on analgesic activity of paracetamol. Neuro Endocrinol Lett. 2010;31(4):507-11. PubMed PMID: 20802454.