LASSBio-881

LASSBio-881

Identifiers
IUPAC name N'-[(3,5-ditert-butyl-4-oxocyclohexa-2,5-dien-1-ylidene)methyl]-6-nitro-1,3-benzodioxole-5-carbohydrazide
CAS Number	929563-84-8  Y
PubChem CID	16721055
ChemSpider	23293401
ChEMBL	ChEMBL234619
Chemical and physical data
Formula	C23H27N3O6
Molar mass	441.484 g·mol−1
3D model (JSmol)	Interactive image
SMILES Oc1c(C(C)(C)C)cc(cc1C(C)(C)C)\C=N\NC(=O)c2cc3OCOc3cc2[N](=O)=O
InChI InChI=1S/C23H27N3O6/c1-22(2,3)15-7-13(8-16(20(15)27)23(4,5)6)11-24-25-21(28)14-9-18-19(32-12-31-18)10-17(14)26(29)30/h7-11,27H,12H2,1-6H3,(H,25,28)/b24-11+ Key:XEYZVZBNMMRXSN-BHGWPJFGSA-N

LASSBio-881 is a drug which acts as both a non-selective partial agonist of the CB₁ and CB₂ cannabinoid receptors, and also as an antagonist of the TRPV1 receptor, as well as having antioxidant effects. It has potent anti-inflammatory and anti-hyperalgesic effects in animal studies. ^{[1] [2]}

• LASSBio-945 has an identical structure sans the nitro FG.

References

1. Duarte CD, Tributino JL, Lacerda DI, Martins MV, Alexandre-Moreira MS, Dutra F, et al. (March 2007). "Synthesis, pharmacological evaluation and electrochemical studies of novel 6-nitro-3,4-methylenedioxyphenyl-N-acylhydrazone derivatives: Discovery of LASSBio-881, a new ligand of cannabinoid receptors". Bioorganic & Medicinal Chemistry. 15 (6): 2421–33. doi:10.1016/j.bmc.2007.01.013. PMID   17275312.
2. Tributino JL, Santos ML, Mesquita CM, Lima CK, Silva LL, Maia RC, et al. (April 2010). "LASSBio-881: an N-acylhydrazone transient receptor potential vanilloid subfamily type 1 antagonist orally effective against the hypernociception induced by capsaicin or partial sciatic ligation". British Journal of Pharmacology. 159 (8): 1716–23. doi:10.1111/j.1476-5381.2010.00672.x. PMC   2925494 . PMID   20401963.