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Lenabasum

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Lenabasum
Clinical data
Trade namesLenabasum
Routes of
administration
Oral
ATC code
  • None
Legal status
Legal status
  • Investigational
Pharmacokinetic data
MetabolismMinimal
Identifiers
  • (6aR,10aR)-3-(1,1-Dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-dibenzo[b,d]pyran-9-carboxylic acid
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC25H36O4
Molar mass400.559 g·mol−1
3D model (JSmol)
  • OC(C1=CC[C@](C(C)(C)OC2=C3C(O)=CC(C(C)(C)CCCCCC)=C2)([H])[C@@]3([H])C1)=O
  • InChI=1S/C25H36O4/c1-6-7-8-9-12-24(2,3)17-14-20(26)22-18-13-16(23(27)28)10-11-19(18)25(4,5)29-21(22)15-17/h10-11,14-16,18-19,26H,6-9,12-13H2,1-5H3,(H,27,28)/t16?,18-,19-/m1/s1 checkY
  • Key:QHGPTMABBHVVQU-VOBHOPKGSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Lenabasum (also known asajulemic acid,1',1'-dimethylheptyl-delta-8-tetrahydrocannabinol-11-oic acid,DMH-D8-THC-11-OIC,AB-III-56,HU-239,IP-751,CPL 7075,CT-3,JBT-101,Anabasum, andResunab) is asyntheticcannabinoid that showsanti-fibrotic andanti-inflammatory effects inpre-clinical studies without causing a subjective "high".[1] Although its design was inspired by ametabolite ofdelta-9-THC known asdelta-9-THC-11-oic acid, lenabasum is ananalog of thedelta-8-THC metabolite delta-8-THC-11-oic acid.[2][3] It is beingdeveloped for the treatment of inflammatory and fibrotic conditions such as systemic sclerosis, dermatomyositis and cystic fibrosis.[4] It does not share theanti-emetic effects of some other cannabinoids, but may be useful for treating chronic inflammatory conditions where inflammation fails to resolve.[5] Side effects include dry mouth, tiredness, and dizziness. The mechanism of action is through activation of theCB2 receptor leading to production of specialized proresolving eicosanoids such aslipoxin A4 andprostaglandin J2. Studies in animals at doses up to 40 mg/kg show minimal psychoactivity of lenabasum, compared to that produced bytetrahydrocannabinol.[6] Lenabasum is being developed by Corbus Pharmaceuticals (formerly JB Therapeutics) for the treatment of orphan chronic life-threatening inflammatory diseases.[7] Development since been discontinued.[8]

References

[edit]
  1. ^Burstein SH, Karst M, Schneider U, Zurier RB (August 2004). "Ajulemic acid: A novel cannabinoid produces analgesia without a "high"".Life Sciences.75 (12):1513–1522.doi:10.1016/j.lfs.2004.04.010.PMID 15240185.
  2. ^Vann RE, Cook CD, Martin BR, Wiley JL (February 2007). "Cannabimimetic properties of ajulemic acid".The Journal of Pharmacology and Experimental Therapeutics.320 (2):678–686.doi:10.1124/jpet.106.111625.PMID 17105826.S2CID 15593252.
  3. ^Motwani MP, Bennett F, Norris PC, Maini AA, George MJ, Newson J, et al. (October 2018)."Potent Anti-Inflammatory and Pro-Resolving Effects of Anabasum in a Human Model of Self-Resolving Acute Inflammation".Clinical Pharmacology and Therapeutics.104 (4):675–686.doi:10.1002/cpt.980.PMC 6175297.PMID 29238967.
  4. ^Mitchell VA, Aslan S, Safaei R, Vaughan CW (July 2005). "Effect of the cannabinoid ajulemic acid on rat models of neuropathic and inflammatory pain".Neuroscience Letters.382 (3):231–235.doi:10.1016/j.neulet.2005.03.019.PMID 15925096.S2CID 582590.
  5. ^Burstein S (June 2005)."Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials".The AAPS Journal.7 (1):E143 –E148.doi:10.1208/aapsj070115.PMC 2751505.PMID 16146336.
  6. ^Vann RE, Cook CD, Martin BR, Wiley JL (February 2007)."Cannabimimetic properties of ajulemic acid".The Journal of Pharmacology and Experimental Therapeutics.320 (2):678–686.doi:10.1124/jpet.106.111625.PMC 2633725.PMID 17105826.
  7. ^"Companies To Watch: Corbus Pharmaceuticals".www.lifescienceleader.com. Retrieved2019-05-20.
  8. ^"Lenabasum".AdisInsight.
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See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)
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