KLS-13019

• CAT Number: I007317
• CAS Number: 1801243-39-9
• Molecular Formula: C22H29NO3
• Molecular Weight: 355.48
• Purity: ≥95%
• Synonyms: KLS-13019; KLS 13019; KLS13019.;1-(3-(((1/’R,2/’R)-2,6-dihydroxy-5/’-methyl-2/’-(prop-1-en-2-yl)-1/’,2/’,3/’,4/’-tetrahydro-[1,1/’-biphenyl]-4-yl)methyl)azetidin-1-yl)ethan-1-one
• Solubility: Soluble in DMSO, not in water
• Storage: 0 - 4°C for short term , or -20°C for long term.
• IUPAC Name: 1-[3-[[3,5-dihydroxy-4-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]phenyl]methyl]azetidin-1-yl]ethanone
• InChI: 1S/C22H29NO3/c1-13(2)18-6-5-14(3)7-19(18)22-20(25)9-16(10-21(22)26)8-17-11-23(12-17)15(4)24/h7,9-10,17-19,25-26H,1,5-6,8,11-12H2,2-4H3/t18-,19+/m0/s1
• InChIKey: VWVIOABMCXYUAS-RBUKOAKNSA-N
• SMILES: CC1=C[C@H]([C@@H](CC1)C(=C)C)C2=C(C=C(C=C2O)CC3CN(C3)C(=O)C)O

KLS-13019 (Cat No.: I007317) is a novel, synthetic cannabidiol (CBD) derivative with enhanced neuroprotective and anti-inflammatory properties. It is being developed for the treatment of neurodegenerative diseases, including neuropathic pain and Parkinson’s disease. Compared to CBD, KLS-13019 exhibits improved bioavailability and potency while reducing oxidative stress and mitochondrial dysfunction. It has shown promise in preclinical studies for treating chemotherapy-induced peripheral neuropathy (CIPN) and other neurological disorders. KLS-13019 is a potential therapeutic candidate for cannabinoid-based drug development with fewer psychoactive effects.

Reference

1:ACS Med Chem Lett. 2016 Feb 10;7(4):424-8. doi: 10.1021/acsmedchemlett.6b00009. eCollection 2016 Apr 14. Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability.Kinney WA,McDonnell ME,Zhong HM,Liu C,Yang L,Ling W,Qian T,Chen Y,Cai Z,Petkanas D,Brenneman DE, PMID: 27096053 PMCID: PMC4834656 DOI: 10.1021/acsmedchemlett.6b00009 Abstract: Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and /drug likeness/, while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.