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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H36O4
Molecular Weight 400.5519
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LENABASUM

SMILES

CCCCCCC(C)(C)c1cc(c2[C@]3([H])CC(=CC[C@@]3([H])C(C)(C)Oc2c1)C(=O)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 400.5519
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Suppression of human monocyte interleukin-1beta production by ajulemic acid, a nonpsychoactive cannabinoid.
2003 Feb 15
Suppression of human macrophage interleukin-6 by a nonpsychoactive cannabinoid acid.
2008 May
Ajulemic acid, a synthetic cannabinoid acid, induces an antiinflammatory profile of eicosanoids in human synovial cells.
2008 Nov 7
Patents

Patents

Sample Use Guides

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
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
by admin
on Fri Jun 25 23:41:10 UTC 2021
Edited
by admin
on Fri Jun 25 23:41:10 UTC 2021
Record UNII
OGN7X90BT8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LENABASUM
INN   USAN  
Official Name English
6H-DIBENZO(B,D)PYRAN-9-CARBOXYLIC ACID, 3-(1,1-DIMETHYLHEPTYL)-6A,7,10,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-, (6AR,10AR)-
Systematic Name English
LENABASUM [INN]
Common Name English
CT-3
Code English
(6AR, 10AR)-3-(1',1'-DIMETHYLHEPTYL)-DELTA-8-TETRAHYDRO-CANNABINOL-9-CARBOXYLIC ACID
Systematic Name English
AJULEMIC ACID
MI  
Common Name English
CPL7075
Code English
(6AR,10AR)-3-(1,1-DIMETHYLHEPTYL)-1-HYDROXY-6,6-DIMETHYL-6A,7,10,10A-TETRAHYDRO-6H-BENZO(C)CHROMENE-9-CARBOXYLIC ACID
Systematic Name English
6H-DIBENZO(B,D)PYRAN-9-CARBOXYLIC ACID, 3-(1,1-DIMETHYLHEPTYL)-6A,7,10,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-, (6AR-TRANS)-
Systematic Name English
LENABASUM [WHO-DD]
Common Name English
(6AR, 10AR)-3-(1,1-DIMETHYLHEPTYL)-DELTA8-TETRAHYDRO-CANNABINOL-9-CARBOXYLIC ACID
Systematic Name English
LENABASUM [USAN]
Common Name English
IP-751
Code English
JBT-101
Code English
HU-239
Code English
RESUNAB
Brand Name English
CPL-7075
Code English
AJULEMIC ACID [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 643618
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
EU-Orphan Drug EU/3/18/2070
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
FDA ORPHAN DRUG 480715
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
FDA ORPHAN DRUG 493415
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
Code System Code Type Description
MERCK INDEX
M1461
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY Merck Index
CAS
137945-48-3
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
NCI_THESAURUS
C174799
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
WIKIPEDIA
AJULEMIC ACID
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
DRUG BANK
DB12193
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
FDA UNII
OGN7X90BT8
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
PUBCHEM
3083542
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
INN
10785
Created by admin on Fri Jun 25 23:41:10 UTC 2021 , Edited by admin on Fri Jun 25 23:41:10 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY