| dbo:abstract |
Pravadoline (WIN 48,098) is an 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. (en) |
| dbo:casNumber |
92623-83-1 |
| dbo:chEMBL |
13178 |
| dbo:fdaUniiCode |
P3JW662TWA |
| dbo:pubchem |
56463 |
| dbo:thumbnail |
wiki-commons:Special:FilePath/Pravadoline.svg?width=300 |
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dbc:WIN_compounds dbr:Bradykinin dbr:Cyclooxygenase dbc:Phenol_ethers dbr:Opioid_receptor dbr:Naloxone dbr:Receptor_antagonist dbr:Prostaglandin dbc:Aminoalkylindoles dbr:Adjuvant dbr:WIN_55,212-2 dbr:AM-630 dbr:Agonist dbr:Analgesic dbc:Benzoylindoles dbr:Nonsteroidal_anti-inflammatory_drug dbc:Morpholines dbr:Hyperalgesia dbr:Indometacin dbr:Cannabinoid dbr:RCS-4 dbr:Nociceptive dbr:IC50 dbr:WIN_54,461 dbr:Cannabinoid_receptor_1 dbr:Randall-Selitto_test dbr:Brewer's_yeast dbr:COX_inhibitor dbr:Antinflammatory |
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none (en) |
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| dbp:h |
26 (xsd:integer) |
| dbp:iupacName |
-[2-methyl-1-indol-3-yl]methanone (en) |
| dbp:legalStatus |
Legal (en) |
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2 (xsd:integer) |
| dbp:o |
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| dbp:pubchem |
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| dbp:smiles |
O=Cc2c4ccccc4nCCN3CCOCC3 (en) |
| dbp:stdinchi |
1 (xsd:integer) |
| dbp:stdinchikey |
MEUQWHZOUDZXHH-UHFFFAOYSA-N (en) |
| dbp:unii |
P3JW662TWA (en) |
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changed (en) |
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| dcterms:subject |
dbc:WIN_compounds dbc:Phenol_ethers dbc:Aminoalkylindoles dbc:Benzoylindoles dbc:Morpholines |
| gold:hypernym |
dbr:Antiinflammatory |
| rdf:type |
owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 yago:WikicatWINCompounds yago:Abstraction100002137 yago:Cognition100023271 yago:Compound105870180 yago:Concept105835747 yago:Content105809192 yago:Element114840755 yago:Idea105833840 yago:Matter100020827 yago:Part113809207 yago:PhysicalEntity100001930 yago:PsychologicalFeature100023100 yago:Quintessence114847103 yago:Relation100031921 dbo:Drug yago:Substance100019613 yago:Whole105869584 yago:WikicatPhenolEthers umbel-rc:DrugProduct |
| rdfs:comment |
Pravadoline (WIN 48,098) is an 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). (en) |
| rdfs:label |
Pravadoline (en) |
| owl:sameAs |
freebase:Pravadoline yago-res:Pravadoline wikidata:Pravadoline dbpedia-sh:Pravadoline dbpedia-sr:Pravadoline https://global.dbpedia.org/id/4tbAV |
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wikipedia-en:Pravadoline?oldid=1094357992&ns=0 |
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wiki-commons:Special:FilePath/Pravadoline.svg |
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wikipedia-en:Pravadoline |
| is dbo:wikiPageRedirects of |
dbr:C23H26N2O3 dbr:WIN_48,098 |
| is dbo:wikiPageWikiLink of |
dbr:Benzydamine dbr:List_of_psychedelic_drugs dbr:BMS-F dbr:C23H26N2O3 dbr:AM-630 dbr:JWH-007 dbr:JWH-200 dbr:Indometacin dbr:Cannabinoid_receptor_antagonist dbr:RCS-4 dbr:List_of_drugs:_Pj–Pra dbr:WIN_48,098 |
| is foaf:primaryTopic of |
wikipedia-en:Pravadoline |
