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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
Structure of LENABASUM

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

HIDE SMILES / InChI

Molecular Formula C25H36O4
Molecular Weight 400.5509
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ajulemic acid, designated as Resunab™, 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

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
OGN7X90BT8
Record Status Validated (UNII)
Record Version