Stereochemistry | ABSOLUTE |
Molecular Formula | C23H33N3O2 |
Molecular Weight | 383.527 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2N(CC3CCCCC3)C=C(C(=O)N4CCN(C)[C@@H](C)C4)C2=CC=C1
InChI
InChIKey=ONXJNAIZJKLJGA-KRWDZBQOSA-N
InChI=1S/C23H33N3O2/c1-17-14-25(13-12-24(17)2)23(27)20-16-26(15-18-8-5-4-6-9-18)22-19(20)10-7-11-21(22)28-3/h7,10-11,16-18H,4-6,8-9,12-15H2,1-3H3/t17-/m0/s1
Molecular Formula | C23H33N3O2 |
Molecular Weight | 383.527 |
Charge | 0 |
Count |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
ORG-28611 (SCH-900,111) is a potent cannabinoid receptor full agonist, developed by Organon International for treatment pain. In preclinical studies, Org 28611 exhibited high affinity for both CB1 and CB2 cannabinoid receptors, as determined by radioligand competition binding assays and rapidly metabolized by mouse and human hepatic microsomes and showed higher total levels in the brain compared to plasma. In clinical trials, Org 28611 does not provide enough sedation for outpatient surgical procedures, does not induce anterograde amnesia and causes undesirable subjective effects at higher doses. However, bolus doses up to 3 μ/kg (with maximum initial plasma concentrations of 24 ng/mL) or mean plasma levels up to 4 ng/mL are well tolerated and make it worthwhile to further explore the analgesic or antiemetic properties.
CNS Activity
Originator
Approval Year
Sourcing
PubMed
Patents
Sample Use Guides
Chinese Hamster Ovary (CHO) cells expressing the human CB1 receptor were used for activity evaluation. Cells were suspended in phenol red / serum free DMEM / F-12 nut mix containing penicillin / streptomycin (50U/50 ¬g/ml) and fungizone (1 ¬g/ml) and seeded into 96 well plates at a density of 3 x 10^4 cells per well (100 ¬l final volume). Cells were incubated overnight (approx. 18 hours at 37°C, 5% CO2/95% air) prior to assay. The test compound (10mM solution in DMSO) was diluted in F12 Nut Mix to give a range of stock solutions from 0.11 mM to 0.11 nM. The stock solutions (10mkl) were added directly to the relevant wells. The plates were incubated at 37°C for 5 hours to allow agonist-induced expression of the luciferase enzyme. Under subdued light, LucLite substrate (Packard; reconstituted as per manufacturer’s instructions; 100 mkl) was added to each well. Plates were covered with Top Seal and then incubated at room temperature for 5 minutes before counting on the Packard TopCount (single photon counting, 0.01 minute count time, 5 minute count delay).