Ajulemic acid

Ajulemic acid

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 of administration	oral
Pharmacokinetic data
Metabolism	minimal
Identifiers
CAS Number	137945-48-3 N
ATC code	none
PubChem	CID: 3083542
ChemSpider	21106251 Y
UNII	OGN7X90BT8 Y
ChEMBL	CHEMBL456341 N
Chemical data
Formula	C25H36O4
Molecular mass	400.551 g/mol
SMILES CC(C)(CCCCCC)c2cc1OC(C)(C)[C@@H]3/C=C\C(C[C@H]3c1c(O)c2)C(O)=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 Y Key:QHGPTMABBHVVQU-VOBHOPKGSA-N Y
NY (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". It is being developed for the treatment of neuropathic pain and inflammatory conditions such as arthritis. 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. 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,. Likewise, there was no difference between ajulemic acid and placebo on the "cannabimimetic" assay when used in humans at therapeutic doses. 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.