Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H36O4 |
Molecular Weight | 400.5509 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC(=CC[C@@]1([H])C(C)(C)OC3=CC(=CC(O)=C23)C(C)(C)CCCCCC)C(O)=O
InChI
InChIKey=YCHYFHOSGQABSW-RTBURBONSA-N
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/h10,14-15,18-19,26H,6-9,11-13H2,1-5H3,(H,27,28)/t18-,19-/m1/s1
Molecular Formula | C25H36O4 |
Molecular Weight | 400.5509 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Ajulemic acid, designated as Resunabâ„¢, is being developed by Corbus Pharmaceuticals, for the treatment of cystic fibrosis, systemic sclerosis, systemic lupus erythematosus.Ajulemic acid (AJA) is a first-in-class, synthetic, orally active, cannabinoid-derived drug that preferentially binds to the CB2 receptor and is nonpsychoactive. In preclinical studies, and in Phase 1 and 2 clinical trials, AJA showed a favorable safety, tolerability, and pharmacokinetic profile. It also demonstrated significant efficacy in preclinical models of inflammation and fibrosis. It suppresses tissue scarring and stimulates endogenous eicosanoids that resolve chronic inflammation and fibrosis without causing immunosuppression. AJA is currently being developed for use in 4 separate but related indications including systemic sclerosis (SSc), cystic fibrosis, dermatomyositis (DM), and systemic lupus erythematosus. Phase 2 clinical trials in the first 3 targets demonstrated that it is safe, is a potential treatment for these orphan diseases and appears to be a potent inflammation-resolving drug with a unique mechanism of action, distinct from the nonsteroidal anti-inflammatory drug (NSAID), and will be useful for treating a wide range of chronic inflammatory diseases.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Suppression of human monocyte interleukin-1beta production by ajulemic acid, a nonpsychoactive cannabinoid. | 2003 Feb 15 |
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Suppression of human macrophage interleukin-6 by a nonpsychoactive cannabinoid acid. | 2008 May |
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Ajulemic acid, a synthetic cannabinoid acid, induces an antiinflammatory profile of eicosanoids in human synovial cells. | 2008 Nov 7 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29638269
Subjects with systemic sclerosis entering this open-label trial will undergo a 28-day screening period, then receive 20 mg BID AJA for 364 days, ending with a 28-day washout after the last dose.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18840450
Fibroblast-like synovial cells (FLS) isolated from tissue obtained at joint replacement surgery or cultured from synovial fluid were treated for 60 min with AjA (10-30 uM), then stimulated with tumor necrosis factor alpha (TNFalpha).
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 11:03:54 GMT 2023
by
admin
on
Sat Dec 16 11:03:54 GMT 2023
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Record UNII |
OGN7X90BT8
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
643618
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EU-Orphan Drug |
EU/3/18/2070
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FDA ORPHAN DRUG |
480715
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FDA ORPHAN DRUG |
493415
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m1461
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137945-48-3
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C174799
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AJULEMIC ACID
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DB12193
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OGN7X90BT8
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100000177553
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3083542
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DTXSID40900959
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10785
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DE-82
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