Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H42O3 |
Molecular Weight | 414.6206 |
Optical Activity | ( + ) |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCC(C)(C)C1=CC(OC)=C([C@H]2C=C(CO)[C@H]3C[C@@H]2C3(C)C)C(OC)=C1
InChI
InChIKey=CFMRIVODIXTERW-BDTNDASRSA-N
InChI=1S/C27H42O3/c1-8-9-10-11-12-26(2,3)19-14-23(29-6)25(24(15-19)30-7)20-13-18(17-28)21-16-22(20)27(21,4)5/h13-15,20-22,28H,8-12,16-17H2,1-7H3/t20-,21+,22-/m0/s1
Molecular Formula | C27H42O3 |
Molecular Weight | 414.6206 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/16316653Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20218623 | https://www.ncbi.nlm.nih.gov/pubmed/16407142 | https://www.ncbi.nlm.nih.gov/pubmed/27634891
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316653
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20218623 | https://www.ncbi.nlm.nih.gov/pubmed/16407142 | https://www.ncbi.nlm.nih.gov/pubmed/27634891
HU-308 ([(1R,2R,5R)-2-[2,6-dimethoxy-4-(2-methyloctan-2-yl)phenyl]-7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl]methanol) is a potent, selective agonist for the CB2 receptor. The synthesis and characterization took place in the laboratory of Prof. Mechoulam at the Hebrew University of Jerusalem in the late 1990s. It has analgesic effects, promotes proliferation of neural stem cells,[3] and protects both liver and blood vessel tissues against oxidative stress via inhibition of TNF-α. In vivo, HU-308 has hypotensive, analgesic, and anti-inflammatory activities in mice that can be reversed by the CB2 receptor antagonist SR 144528 but not the CB1 receptor antagonist rimonabant. Pretreatment of mice with HU-308 decreases the I/R-induced tissue damage, inflammatory cell infiltration, tissue, and serum TNF-α, MIP-1, and MIP-2 levels, tissue lipid peroxidation, and apoptosis. HU-308 increases proliferation of HT29 colon cancer cells and growth of tumors in an HT29 mouse xenograft model. The physiological and toxicological properties of this compound have not been evaluated in humans.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20218623 |
22.7 nM [Ki] | ||
Target ID: CHEMBL5845 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20346682 |
|||
Target ID: CHEMBL5871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20346682 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316653 |
Primary | Unknown Approved UseUnknown |
||
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16316653
Rats were treated with HU-308 (0.3-30 mg/kg i.p.)
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27634891
Cells were set up 4x103 cells per well of a 96-well plate and were cultured in DMEM medium supplemented with 10% FCS overnight. The medium was replaced for serum-free DMEM medium and cells were incubated for 48h with HU-308 (0.001, 0.01, 0.1, 1 and 10mkM). Cell viability was assayed by Cell Counting Kit-8 (CCK-8).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:42:38 GMT 2023
by
admin
on
Fri Dec 15 16:42:38 GMT 2023
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Record UNII |
8I5L034D55
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Record Status |
Validated (UNII)
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Record Version |
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WIKIPEDIA |
Designer-drugs-HU-308
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FDA ORPHAN DRUG |
734920
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300000025391
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11976
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11553430
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256934-39-1
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C184881
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8I5L034D55
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KL-18
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HU-308
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DTXSID801017327
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TARGET -> AGONIST |
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ACTIVE MOIETY |
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