Ajulemic acid

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Ajulemic acid
Ajulemicacid.png
Systematic (IUPAC) name
(6aR,10aR)-3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-6H-Dibenzo(b,d)pyran-9-carboxylic acid
Clinical data
Trade names Resunab
Legal status
  • patent pending
Routes oral
Pharmacokinetic data
Metabolism minimal
Identifiers
CAS number 137945-48-3 N
ATC code None
PubChem CID 3083542
ChemSpider 21106251 YesY
ChEMBL CHEMBL456341 N
Chemical data
Formula C25H36O4 
Mol. mass 400.551 g/mol
 N (what is this?)  (verify)

Ajulemic acid (AB-III-56, HU-239, IP-751, CPL 7075, CT-3, Resunab) is a synthetic cannabinoid derivative of the non-psychoactive THC metabolite 11-nor-9-carboxy-THC that shows useful analgesic and anti-inflammatory effects without causing a subjective "high".[1] It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis.[2] It does not however share the anti-emetic effects of other cannabinoids but may be useful for treating pain and chronic inflammatory conditions where nausea is not present.[3] Side effects include dry mouth, tiredness and dizziness. The mechanism of action has not yet been fully established, but ajulemic acid may activate the CB2 receptor in the periphery leading to production of resolving eicosanoids. Studies in animals at doses up to 40 mg/kg show minimal psychoactivity of ajulemic acid, comparable to that produced by tetrahydrocannabinol,.[4] Likewise, there was no difference between ajulemic acid and placebo on the "cannabimimetic" assay when used in humans at therapeutic doses.[5][6] A new highly purified composition of ajulemic acid named Resunab is being developed by Corbus Pharmaceuticals (formerly JB Therapeutics)for the treatment of orphan life-threatening inflammatory diseases.

References[edit]

  1. ^ Burstein, S.; Karst, M.; Schneider, U.; Zurier, R. (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.  edit
  2. ^ Mitchell, V.; Aslan, S.; Safaei, R.; Vaughan, C. (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.  edit
  3. ^ Burstein, S. (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.  edit
  4. ^ Vann, R.; Cook, C.; Martin, B.; Wiley, J. (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.  edit
  5. ^ Sumariwalla, P.; Gallily, R.; Tchilibon, S.; Fride, E.; Mechoulam, R.; Feldmann, M. (2004). "A novel synthetic, nonpsychoactive cannabinoid acid (HU-320) with antiinflammatory properties in murine collagen-induced arthritis". Arthritis and rheumatism 50 (3): 985–998. doi:10.1002/art.20050. PMID 15022343.   edit
  6. ^ Sumariwalla, P.F., et al. (2004). "Reply". Arthritis & Rheumatism 50 (12): 4079. doi:10.1002/art.20806.  edit