Lenabasum

Lenabasum
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)

Lenabasum (also known as ajulemic 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, and Resunab) is a synthetic cannabinoid that shows anti-fibrotic and anti-inflammatory effects in pre-clinical studies without causing a subjective "high".^[1] Although its design was inspired by a metabolite of delta-9-THC known as delta-9-THC-11-oic acid, lenabasum is an analog of the delta-8-THC metabolite delta-8-THC-11-oic acid.^[2]^[3] It is being developed for the treatment of inflammatory and fibrotic conditions such as systemic sclerosis, dermatomyositis and cystic fibrosis.^[4] 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.^[5] 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 lenabasum, compared to that produced by tetrahydrocannabinol.^[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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ "Companies To Watch: Corbus Pharmaceuticals". www.lifescienceleader.com. Retrieved 2019-05-20.
^ "Lenabasum". AdisInsight.

[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): 1513–1522. 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.

[pmid15925096-4] 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.

[pmid16146336-5] 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. Retrieved 2019-05-20.

[8] "Lenabasum". AdisInsight.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]