Compound: Pravadoline
SMILES: O=C(c1ccc(OC)cc1)c2c3c(cccc3)n(c2C)CCN4CCOCC4
InChIKey: MEUQWHZOUDZXHH-UHFFFAOYSA-N
Synonyms: Pravadoline, 92623-83-1, Pravadolina, Pravadolinum, P3JW662TWA, DTXSID2046127, DTXCID0026127, Methanone, (4-methoxyphenyl)(2-methyl-1-(2-(4-morpholinyl)ethyl)-1H-indol-3-yl)-, RefChem:929935, (4-Methoxyphenyl)(2-methyl-1-(2-morpholinoethyl)-1H-indol-3-yl)methanone, Pravadoline [INN], WIN 48098, MFCD00864378, CHEMBL13178, (4-methoxyphenyl)-[2-methyl-1-(2-morpholin-4-ylethyl)indol-3-yl]methanone, NCGC00160396-01, Pravadoline, Pravadoline Maleate, (4-Methoxy-phenyl)-[2-methyl-1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl]-methanone, SMR001550504, CAS-92623-83-1, Pravadolinum [INN-Latin], UNII-P3JW662TWA, Pravadolina [INN-Spanish], Win-48098, MLS004774040, MLS006010335, orb341853, SCHEMBL488940, Pravadoline(WIN 48,098), Pravadoline (WIN 48,098), Pravadoline(WIN 48,098)?, SCHEMBL30353006, Pravadoline, (WIN 48,098), MEUQWHZOUDZXHH-UHFFFAOYSA-N, HMS2089L05, p-methoxyphenyl 2-methyl-1-(2-morpholinoethyl)indol-3-yl ketone, Tox21_111785, 3-(4-methoxybenzoyl)-2-methyl-1-[2-(morpholin-4-yl)ethyl]-1H-indole, BDBM50008029, (4-methoxyphenyl)-[2-methyl-1-(2-morpholinoethyl)indol-3-yl]methanone, AKOS000278689, Tox21_111785_1, CCG-208742, DS-1893, FP02360, (4-Methoxyphenyl)(2-methyl-1-(2-(4-morpholinyl)ethyl)-1H-indol-3-yl)methanone, NCGC00160396-02, NCGC00160396-03, NCGC00160396-04, NS00009981, AB01275459-01, SR-05000001465, Q7238828, SR-05000001465-1, BRD-K46209126-001-01-5, BRD-K46209126-001-06-4, (4-Methoxyphenyl){2-methyl-1-[2-(morpholin-4-yl)ethyl]-1H-indol-3-yl}methanone, (s-cis) -(4-Methoxy-phenyl)-[2-methyl-1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl]-methanone
Theoretical properties:
molecular_formula: C23H26N2O3
molecular_weight: 378.5 g/mol
exact_mass: 378.19434270 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 6
heavy_atom_count: 28
topological_polar_surface_area: 43.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
chembl: PRAVADOLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Pravadoline (WIN 48,098) is an anti-inflammatory and analgesic drug with an IC50 of 4.9 μM and a Ki of 2511 nM at CB1, related in structure to nonsteroidal anti-inflammatory drugs (NSAIDs) such as indometacin. It was developed in the 1980s as a new antiinflammatory and prostaglandin synthesis inhibitor, acting through inhibition of the enzyme cyclooxygenase (COX).
However, pravadoline was found to exhibit unexpectedly strong analgesic effects, which appeared at doses ten times smaller than the effective anti-inflammatory dose and so could not be explained by its action as a COX inhibitor. These effects were not blocked by opioid antagonists such as naloxone, and it was eventually discovered that pravadoline represented the first compound from a novel class of cannabinoid agonists, the aminoalkylindoles.
Pravadoline was never developed for use as an analgesic, partly due to toxicity concerns (although these were later shown to be a result of the salt form that the drug had been prepared in rather than from the pravadoline itself), however the discovery of cannabinoid activity in this structurally novel family of drugs led to the discovery of several new cannabinoid agonists, including the drug WIN 55,212-2, which is now widely used in scientific research.