OL-135
featured

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

MedKoo CAT#: 522478

CAS#: 681135-77-3

Description: OL-135 is a CNS penetrant, highly potent and selective reversible inhibitor of FAAH. OL-135 exhibits analgesic pharmacology in various animal models without the motor impairment associated with direct CB1 agonism.


Price and Availability

Size
Price

5mg
USD 240
Size
Price

25mg
USD 590
Size
Price

OL-135, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 522478
Name: OL-135
CAS#: 681135-77-3
Chemical Formula: C21H22N2O2
Exact Mass: 334.16813
Molecular Weight: 334.419
Elemental Analysis: C, 75.42; H, 6.63; N, 8.38; O, 9.57


Synonym: OL-135; OL 135; OL135.

IUPAC/Chemical Name: 1-Oxo-1-[5-(2-pyridyl)oxazol-2-yl]-7-phenylheptane

InChi Key: ILOIOIGZFHGSMS-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H22N2O2/c24-19(14-7-2-1-4-10-17-11-5-3-6-12-17)21-23-16-20(25-21)18-13-8-9-15-22-18/h3,5-6,8-9,11-13,15-16H,1-2,4,7,10,14H2

SMILES Code: O=C(C1=NC=C(C2=NC=CC=C2)O1)CCCCCCC3=CC=CC=C3


Technical Data

Appearance:
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).

Harmonized System Code:
293490


References

1: Duncan KK, Otrubova K, Boger DL. α-Ketoheterocycle inhibitors of fatty acid amide hydrolase: exploration of conformational constraints in the acyl side chain. Bioorg Med Chem. 2014 May 1;22(9):2763-70. doi: 10.1016/j.bmc.2014.03.013. Epub 2014 Mar 18. PubMed PMID: 24690529; PubMed Central PMCID: PMC4029506.

2: Otrubova K, Cravatt BF, Boger DL. Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase. J Med Chem. 2014 Feb 13;57(3):1079-89. doi: 10.1021/jm401820q. Epub 2014 Jan 23. PubMed PMID: 24456116; PubMed Central PMCID: PMC3940414.

3: Wu H, Kelley CJ, Pino-Figueroa A, Vu HD, Maher TJ. Macamides and their synthetic analogs: evaluation of in vitro FAAH inhibition. Bioorg Med Chem. 2013 Sep 1;21(17):5188-97. doi: 10.1016/j.bmc.2013.06.034. Epub 2013 Jun 27. PubMed PMID: 23891163.

4: Otrubova K, Brown M, McCormick MS, Han GW, O'Neal ST, Cravatt BF, Stevens RC, Lichtman AH, Boger DL. Rational design of fatty acid amide hydrolase inhibitors that act by covalently bonding to two active site residues. J Am Chem Soc. 2013 Apr 24;135(16):6289-99. doi: 10.1021/ja4014997. Epub 2013 Apr 12. PubMed PMID: 23581831; PubMed Central PMCID: PMC3678763.

5: Caprioli A, Coccurello R, Rapino C, Di Serio S, Di Tommaso M, Vertechy M, Vacca V, Battista N, Pavone F, Maccarrone M, Borsini F. The novel reversible fatty acid amide hydrolase inhibitor ST4070 increases endocannabinoid brain levels and counteracts neuropathic pain in different animal models. J Pharmacol Exp Ther. 2012 Jul;342(1):188-95. doi: 10.1124/jpet.111.191403. Epub 2012 Apr 18. PubMed PMID: 22514334.

6: Scott CW, Tian G, Yu XH, Paschetto KA, Wilkins DE, Meury L, Cao CQ, Varnes J, Edwards PD. Biochemical characterization and in vitro activity of AZ513, a noncovalent, reversible, and noncompetitive inhibitor of fatty acid amide hydrolase. Eur J Pharmacol. 2011 Sep 30;667(1-3):74-9. doi: 10.1016/j.ejphar.2011.05.052. Epub 2011 Jun 1. PubMed PMID: 21645511.

7: Booker L, Kinsey SG, Abdullah RA, Blankman JL, Long JZ, Ezzili C, Boger DL, Cravatt BF, Lichtman AH. The fatty acid amide hydrolase (FAAH) inhibitor PF-3845 acts in the nervous system to reverse LPS-induced tactile allodynia in mice. Br J Pharmacol. 2012 Apr;165(8):2485-96. doi: 10.1111/j.1476-5381.2011.01445.x. PubMed PMID: 21506952; PubMed Central PMCID: PMC3423256.

8: Ezzili C, Mileni M, McGlinchey N, Long JZ, Kinsey SG, Hochstatter DG, Stevens RC, Lichtman AH, Cravatt BF, Bilsky EJ, Boger DL. Reversible competitive α-ketoheterocycle inhibitors of fatty acid amide hydrolase containing additional conformational constraints in the acyl side chain: orally active, long-acting analgesics. J Med Chem. 2011 Apr 28;54(8):2805-22. doi: 10.1021/jm101597x. Epub 2011 Mar 23. PubMed PMID: 21428410; PubMed Central PMCID: PMC3085948.

9: Mileni M, Garfunkle J, Ezzili C, Kimball FS, Cravatt BF, Stevens RC, Boger DL. X-ray crystallographic analysis of alpha-ketoheterocycle inhibitors bound to a humanized variant of fatty acid amide hydrolase. J Med Chem. 2010 Jan 14;53(1):230-40. doi: 10.1021/jm9012196. PubMed PMID: 19924997; PubMed Central PMCID: PMC2804032.

10: Mileni M, Garfunkle J, DeMartino JK, Cravatt BF, Boger DL, Stevens RC. Binding and inactivation mechanism of a humanized fatty acid amide hydrolase by alpha-ketoheterocycle inhibitors revealed from cocrystal structures. J Am Chem Soc. 2009 Aug 5;131(30):10497-506. doi: 10.1021/ja902694n. PubMed PMID: 19722626; PubMed Central PMCID: PMC2739126.

11: Kinsey SG, Long JZ, O'Neal ST, Abdullah RA, Poklis JL, Boger DL, Cravatt BF, Lichtman AH. Blockade of endocannabinoid-degrading enzymes attenuates neuropathic pain. J Pharmacol Exp Ther. 2009 Sep;330(3):902-10. doi: 10.1124/jpet.109.155465. Epub 2009 Jun 5. PubMed PMID: 19502530; PubMed Central PMCID: PMC2729802.

12: Schlosburg JE, Boger DL, Cravatt BF, Lichtman AH. Endocannabinoid modulation of scratching response in an acute allergenic model: a new prospective neural therapeutic target for pruritus. J Pharmacol Exp Ther. 2009 Apr;329(1):314-23. doi: 10.1124/jpet.108.150136. Epub 2009 Jan 23. PubMed PMID: 19168707; PubMed Central PMCID: PMC2670585.

13: Naidu PS, Booker L, Cravatt BF, Lichtman AH. Synergy between enzyme inhibitors of fatty acid amide hydrolase and cyclooxygenase in visceral nociception. J Pharmacol Exp Ther. 2009 Apr;329(1):48-56. doi: 10.1124/jpet.108.143487. Epub 2008 Dec 31. PubMed PMID: 19118134; PubMed Central PMCID: PMC2670588.

14: Garfunkle J, Ezzili C, Rayl TJ, Hochstatter DG, Hwang I, Boger DL. Optimization of the central heterocycle of alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase. J Med Chem. 2008 Aug 14;51(15):4392-403. doi: 10.1021/jm800136b. Epub 2008 Jul 16. PubMed PMID: 18630870; PubMed Central PMCID: PMC2556205.

15: Timmons A, Seierstad M, Apodaca R, Epperson M, Pippel D, Brown S, Chang L, Scott B, Webb M, Chaplan SR, Breitenbucher JG. Novel ketooxazole based inhibitors of fatty acid amide hydrolase (FAAH). Bioorg Med Chem Lett. 2008 Mar 15;18(6):2109-13. doi: 10.1016/j.bmcl.2008.01.091. Epub 2008 Jan 30. PubMed PMID: 18289847.

16: Kimball FS, Romero FA, Ezzili C, Garfunkle J, Rayl TJ, Hochstatter DG, Hwang I, Boger DL. Optimization of alpha-ketooxazole inhibitors of fatty acid amide hydrolase. J Med Chem. 2008 Feb 28;51(4):937-47. doi: 10.1021/jm701210y. Epub 2008 Feb 5. PubMed PMID: 18247553; PubMed Central PMCID: PMC2734917.

17: Hardouin C, Kelso MJ, Romero FA, Rayl TJ, Leung D, Hwang I, Cravatt BF, Boger DL. Structure-activity relationships of alpha-ketooxazole inhibitors of fatty acid amide hydrolase. J Med Chem. 2007 Jul 12;50(14):3359-68. Epub 2007 Jun 9. PubMed PMID: 17559203; PubMed Central PMCID: PMC2531194.

18: Romero FA, Du W, Hwang I, Rayl TJ, Kimball FS, Leung D, Hoover HS, Apodaca RL, Breitenbucher JG, Cravatt BF, Boger DL. Potent and selective alpha-ketoheterocycle-based inhibitors of the anandamide and oleamide catabolizing enzyme, fatty acid amide hydrolase. J Med Chem. 2007 Mar 8;50(5):1058-68. Epub 2007 Feb 6. PubMed PMID: 17279740; PubMed Central PMCID: PMC2531193.

19: Naidu PS, Varvel SA, Ahn K, Cravatt BF, Martin BR, Lichtman AH. Evaluation of fatty acid amide hydrolase inhibition in murine models of emotionality. Psychopharmacology (Berl). 2007 May;192(1):61-70. Epub 2007 Feb 6. PubMed PMID: 17279376.

20: Zhang D, Saraf A, Kolasa T, Bhatia P, Zheng GZ, Patel M, Lannoye GS, Richardson P, Stewart A, Rogers JC, Brioni JD, Surowy CS. Fatty acid amide hydrolase inhibitors display broad selectivity and inhibit multiple carboxylesterases as off-targets. Neuropharmacology. 2007 Mar;52(4):1095-105. Epub 2007 Jan 9. PubMed PMID: 17217969.