681135-77-3
Chemical Structure
OL-135
- CAS No.: 681135-77-3
- Formula:C21H22N2O2
- Molecular Weight:334.41
IUPAC Name: 7-phenyl-1-(5-(pyridin-2-yl)oxazol-2-yl)heptan-1-one
InChIKey: ILOIOIGZFHGSMS-UHFFFAOYSA-N
SMILES: O=C(CCCCCCC1=CC=CC=C1)C2=NC=C(C3=CC=CC=N3)O2
Biological Activity: OL-135 is a blood-brain barrier-permeable α-ketoheterocyclic FAAH and Carboxylesterase inhibitor (mouse FAAH IC50 = 2.1 nM; human FAAH IC50 = 14 nM). OL-135 selectively forms a hemiketal with the catalytic Ser241, increasing Anandamide (HY-10863) and fatty acid ethanolamide levels, thereby promoting the acquisition and extinction of spatial memory and producing CB1/CB2/opioid receptor-dependent analgesia. OL-135 can be used in the research of neuropathic pain, inflammatory pain, post-traumatic stress disorder, and obsessive-compulsive disorder[1][2][3][4][5][6][7][8][9][10].
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OL-135 | OL-135 is a blood-brain barrier-permeable α-ketoheterocyclic FAAH and Carboxylesterase inhibitor (mouse FAAH IC50 = 2.1 nM; human FAAH IC50 = 14 nM). OL-135 selectively forms a hemiketal with the catalytic Ser241, increasing Anandamide (HY-10863) and fatty acid ethanolamide levels, thereby promoting the acquisition and extinction of spatial memory and producing CB1/CB2/opioid receptor-dependent analgesia. OL-135 can be used in the research of neuropathic pain, inflammatory pain, post-traumatic stress disorder, and obsessive-compulsive disorder. | |||||||||||||||||||||
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References
- [1]. Varvel SA, et al. Inhibition of fatty-acid amide hydrolase accelerates acquisition and extinction rates in a spatial memory task. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology. 2007 May;32(5):1032-41.
- [2]. Zhang D, et al. Fatty acid amide hydrolase inhibitors display broad selectivity and inhibit multiple carboxylesterases as off-targets. Neuropharmacology. 2007 Mar;52(4):1095-105. [Content Brief]
- [3]. Lichtman AH, et al. Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity. The Journal of pharmacology and experimental therapeutics. 2004 Nov;311(2):441-8.
- [4]. Scott CW, et al. Biochemical characterization and in vitro activity of AZ513, a noncovalent, reversible, and noncompetitive inhibitor of fatty acid amide hydrolase. European journal of pharmacology. 2011 Sep 30;667(1-3):74-9. [Content Brief]
- [5]. Kinsey SG, et al. Blockade of endocannabinoid-degrading enzymes attenuates neuropathic pain. The Journal of pharmacology and experimental therapeutics. 2009 Sep;330(3):902-10.
- [6]. Mileni M, et al. Binding and inactivation mechanism of a humanized fatty acid amide hydrolase by alpha-ketoheterocycle inhibitors revealed from cocrystal structures. Journal of the American Chemical Society. 2009 Aug 05;131(30):10497-506.
- [7]. Santana PAL, et al. Design of arylfurans as potential FAAH inhibitors: therapeutic potential in pain management. Bioorganic & medicinal chemistry. 2026 Jan 01;132:118471.
- [8]. Booker L, et al. The fatty acid amide hydrolase (FAAH) inhibitor PF-3845 acts in the nervous system to reverse LPS-induced tactile allodynia in mice. British journal of pharmacology. 2012 Apr;165(8):2485-96. [Content Brief]
- [9]. Otrubova K, et al. Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase. Journal of medicinal chemistry. 2014 Feb 13;57(3):1079-89.
- [10]. Hardouin C, et al. Structure-activity relationships of alpha-ketooxazole inhibitors of fatty acid amide hydrolase. Journal of medicinal chemistry. 2007 Jul 12;50(14):3359-68.
