Lixosicone

Lixosicone (AEF0117, 3β-(4-methoxybenzyloxy)pregn-5-en-20-one) is a compound derived from pregnenolone by Aelis Farma, which acts as a biased allosteric modulator of the cannabinoid CB₁ receptor, representing a new class of compounds referred to as CB₁-selective signalling-specific inhibitors (CB₁-SSi). It binds to an allosteric site on the CB₁ receptor and modifies the downstream signalling produced as a result of CB₁ activation, preventing CB₁ mediated changes to mitogen-activated protein kinase (MAPK) phosphorylation but without affecting the signalling mediated by cyclic AMP. Unlike pregnenolone, AEF0117 is specific for the CB₁-SSi activity and lacks the neurosteroid action typical of many structurally related compounds.^[1]

CAS Number

• 1610878-71-1 ^N

PubChem CID

• 139433957

ChemSpider

• 129421614

FormulaC₂₉H₄₀O₃

Quick facts Identifiers, CAS Number ...

Lixosicone

Identifiers
IUPAC name 1-[(3S,8S,9S,10R,13S,14S,17S)-3-[(4-methoxyphenyl)methoxy]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
CAS Number	1610878-71-1 N
PubChem CID	139433957
ChemSpider	129421614
Chemical and physical data
Formula	C29H40O3
Molar mass	436.636 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)OCC5=CC=C(C=C5)OC)C)C
InChI InChI=1S/C29H40O3/c1-19(30)25-11-12-26-24-10-7-21-17-23(32-18-20-5-8-22(31-4)9-6-20)13-15-28(21,2)27(24)14-16-29(25,26)3/h5-9,23-27H,10-18H2,1-4H3/t23-,24-,25+,26-,27-,28-,29+/m0/s1 Key:AAZPIQPULVRHOW-SFKJMYEFSA-N

Close

In Phase II human clinical trials in patients diagnosed with cannabis use disorder, AEF0117 was found to partly but not completely block the effects of THC, and reduced cannabis self-administration but without producing an acute withdrawal syndrome and with relatively mild side effects. It is hoped that compounds of this type may be useful either as medications for the treatment of cannabinoid dependence, or could be used alongside medicinal cannabis to reduce unwanted side effects while retaining therapeutic efficacy.^[2]