Movatterモバイル変換


[0]ホーム

URL:


Jump to content
WikipediaThe Free Encyclopedia
Search

KLS-13019

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
KLS-13019
Identifiers
  • 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
CAS Number
PubChemCID
Chemical and physical data
FormulaC22H29NO3
Molar mass355.478 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C(C(=C1F)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
  • 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
  • Key:VWVIOABMCXYUAS-RBUKOAKNSA-N

KLS-13019 is acannabidiol derivative that has been modified on the side chain to improvesolubility and tissue penetration properties. It was developed and patented byNeuropathix subsidiaryKannalife and found to be 50x more potent than cannabidiol as aneuroprotective agent, thought to be mediated by modulation of themitochondrialsodium-calcium exchanger andGPR55. It also had a highertherapeutic index than cannabidiol.[1][2][3] Both KLS-13019 and cannabidiol, prevented the development ofCIPN, while only KLS-13019 uniquely reversedneuropathic pain fromchemotherapy. KLS-13019 binds to fewer biological targets than cannabidiol and KLS-13019 may possess the unique ability to reverse addictive behaviour, an effect not observed with cannabidiol.[4] Recent studies have also demonstrated that KLS-13019 influences neuroinflammatory responses in primary neuronal cultures, an effect that is dependent on the fatty acyl composition oflysophosphatidylinositol. This suggests an interaction between KLS-13019 and lipid signaling pathways, potentially involvingGPR55, a receptor implicated in neuroinflammatory modulation.[5]

See also

[edit]


References

[edit]
  1. ^Kinney WA, McDonnell ME, Zhong HM, Liu C, Yang L, Ling W, et al. (April 2016)."Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability".ACS Medicinal Chemistry Letters.7 (4):424–8.doi:10.1021/acsmedchemlett.6b00009.PMC 4834656.PMID 27096053.
  2. ^Brenneman DE, Petkanas D, Kinney WA (September 2018)."Pharmacological Comparisons Between Cannabidiol and KLS-13019".Journal of Molecular Neuroscience.66 (1):121–134.doi:10.1007/s12031-018-1154-7.PMC 6150782.PMID 30109468.
  3. ^Brenneman DE, Kinney WA, Ward SJ (August 2019)."Knockdown siRNA Targeting the Mitochondrial Sodium-Calcium Exchanger-1 Inhibits the Protective Effects of Two Cannabinoids Against Acute Paclitaxel Toxicity".Journal of Molecular Neuroscience.68 (4):603–619.doi:10.1007/s12031-019-01321-z.PMC 6615992.PMID 31077084.
  4. ^Foss JD, Farkas DJ, Huynh LM, Kinney WA, Brenneman DE, Ward SJ (April 2021)."Behavioral and pharmacological effects of cannabidiol (CBD) and the CBD analogue KLS‐13019 in mouse models of pain and reinforcement".British Journal of Pharmacology.178 (15):3067–3078.doi:10.1111/bph.15486.PMID 33822373.S2CID 233035597.
  5. ^Brenneman DE, Petkanas D, Ippolito M, Ward SJ (2025)."Effect of Fatty Acyl Composition for Lysophosphatidylinositol on Neuroinflammatory Responses in Primary Neuronal Cultures".Journal of Molecular Neuroscience.75 (1): 35.doi:10.1007/s12031-025-02326-7.PMC 11760249.PMID 39866868.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
Stub icon

Thiscannabinoid related article is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=KLS-13019&oldid=1280590991"
Categories:
Hidden categories:

[8]ページ先頭

©2009-2025 Movatter.jp