Ajulemic acid

Ajulemic acid
Clinical data
Trade names	Lenabasum
Routes of; administration	Oral
ATC code	None;
Legal status
Legal status	Investigational;
Pharmacokinetic data
Metabolism	Minimal
Identifiers
	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;
CAS Number	137945-48-3 ;
PubChem CID	3083542;
ChemSpider	21106251 ;
UNII	OGN7X90BT8;
ChEMBL	ChEMBL456341 ;
CompTox Dashboard (EPA)	DTXSID40900959 ;
Chemical and physical data
Formula	C25H36O4
Molar mass	400.559 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC(C1=CC[C@](C(C)(C)OC2=C3C(O)=CC(C(C)(C)CCCCCC)=C2)([H])[C@@]3([H])C1)=O;
	InChI 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 ; Key:QHGPTMABBHVVQU-VOBHOPKGSA-N ;
	(what is this?) (verify)

Ajulemic acid (AB-III-56, HU-239, IP-751, CPL 7075, CT-3, JBT-101, Anabasum, Resunab) is a synthetic cannabinoid derivative of the THC metabolite 11-nor-9-carboxy-THC that shows anti-fibrotic and anti-inflammatory effects in pre-clinical studies without causing a subjective "high".[1] It is being developed for the treatment of inflammatory and fibrotic conditions such as systemic sclerosis, dermatomyositis and cystic fibrosis.[2] It does not share the anti-emetic effects of some other cannabinoids, but may be useful for treating chronic inflammatory conditions where inflammation fails to resolve.[3] Side effects include dry mouth, tiredness, and dizziness. The mechanism of action is through activation of the CB₂ receptor leading to production of specialized proresolving eicosanoids such as lipoxin A4 and Prostaglandin J2. Studies in animals at doses up to 40 mg/kg show minimal psychoactivity of ajulemic acid, compared to that produced by tetrahydrocannabinol.[4] A composition of ajulemic acid named Lenabasum (formerly Anabasum, Resunab) is being developed by Corbus Pharmaceuticals (formerly JB Therapeutics) for the treatment of orphan chronic life-threatening inflammatory diseases.[5]

References

Burstein SH, Karst M, Schneider U, Zurier RB (August 2004). "Ajulemic acid: A novel cannabinoid produces analgesia without a "high"". Life Sciences. 75 (12): 1513–22. doi:10.1016/j.lfs.2004.04.010. PMID 15240185.
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): 231–5. doi:10.1016/j.neulet.2005.03.019. PMID 15925096. S2CID 582590.
Burstein S (June 2005). "Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials". The AAPS Journal. 7 (1): E143-8. doi:10.1208/aapsj070115. PMC 2751505. PMID 16146336.
Vann RE, Cook CD, Martin BR, Wiley JL (February 2007). "Cannabimimetic properties of ajulemic acid". The Journal of Pharmacology and Experimental Therapeutics. 320 (2): 678–86. doi:10.1124/jpet.106.111625. PMC 2633725. PMID 17105826.
"Companies To Watch: Corbus Pharmaceuticals". www.lifescienceleader.com. Retrieved 2019-05-20.

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[pmid15240185-1] Burstein SH, Karst M, Schneider U, Zurier RB (August 2004). "Ajulemic acid: A novel cannabinoid produces analgesia without a "high"". Life Sciences. 75 (12): 1513–22. doi:10.1016/j.lfs.2004.04.010. PMID 15240185.

[pmid15925096-2] 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): 231–5. doi:10.1016/j.neulet.2005.03.019. PMID 15925096. S2CID 582590.

[pmid16146336-3] Burstein S (June 2005). "Ajulemic acid (IP-751): synthesis, proof of principle, toxicity studies, and clinical trials". The AAPS Journal. 7 (1): E143-8. doi:10.1208/aapsj070115. PMC 2751505. PMID 16146336.

[4] Vann RE, Cook CD, Martin BR, Wiley JL (February 2007). "Cannabimimetic properties of ajulemic acid". The Journal of Pharmacology and Experimental Therapeutics. 320 (2): 678–86. doi:10.1124/jpet.106.111625. PMC 2633725. PMID 17105826.

[5] "Companies To Watch: Corbus Pharmaceuticals". www.lifescienceleader.com. Retrieved 2019-05-20.