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07-SEPTEMBER-2008 03:17:44 - Pravadoline Pravadoline Systematic IUPAC name 4-methoxyphenyl-2-methyl-1-2-morpholin-4-ylethylindol-3-ylmethanone Identifiers CAS number 92623-83-1 ATC code ? PubChem 56463 Chemical data Formula C23H26N2O3 Mol. mass 378.46 g/mol Pharmacokinetic data Bioavailability ? Metabolism ? Half life ? Excretion ? Therapeutic considerations Pregnancy cat. ? Legal status Legal Routes ? Pravadoline WIN 48098 is an antiinflammatory and analgesic drug, related in structure to non-steroidal antinflammtory 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,1 and it was eventually discovered that pravadoline represented the first compound from a novel class of cannabinoid agonists, the aminoalkylindoles.2 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,3 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.45 Tablets This pharmacology-related article is a stub. References ^ Haubrich DR, Ward SJ, Baizman E, et al 1990. Pharmacology of pravadoline: a new analgesic agent. J. Pharmacol. Exp. Ther. 255 2: 511-22. PMID 2243340. ^ Bell MR, D'Ambra TE, Kumar V, et al 1991. Antinociceptive aminoalkylindoles. J. Med. Chem. 34 3: 1099-110. PMID 1900533. ^ Everett RM, Descotes G, Rollin M, et al 1993. Nephrotoxicity of pravadoline maleate WIN 48098-6 in dogs: evidence of maleic acid-induced acute tubular necrosis. Fundam Appl Toxicol 21 1: 59-65. PMID 8365586. ^ D'Ambra TE, Estep KG, Bell MR, et al 1992. Conformationally restrained analogues of pravadoline: nanomolar potent, enantioselective, aminoalkylindole agonists of the cannabinoid receptor. J. Med. Chem. 35 1: 124-35. PMID 1732519. ^ Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR 1992. Aminoalkylindole analogs: cannabimimetic activity of a class of compounds structurally distinct from delta 9-tetrahydrocannabinol. J. Pharmacol. Exp. Ther. 263 3: 1118-26. PMID 1335057. v d e Cannabinoids Plant cannabinoids CBD CBDV CBN CBG CBV CBL THC THC-C4 THCV Cannabinoid metabolites 11-Hydroxy-THC 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide Anandamide or AEA 2-Arachidonoylglycerol 2-AG 2-Arachidonyl glyceryl ether noladin ether Virodhamine N-arachidonoyl-dopamine NADA; Oleamide Synthetic cannabinoid agonists Classical cannabinoids Dibenzopyrans A-41988 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-938 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol HU-211 DMHP Dronabinol HU-210 JWH-051 JWH-133 JWH-139 L-759,633 L-759,656 Levonantradol Nabilone Nabitan O-806 O-823 O-1057 O-1125 O-1238 O-2545 O-2694 Parahexyl THC-O-acetate THC-O-phosphate Nonclassical cannabinoids CP 47,497 CP 55,244 CP 55,940 HU-308 2-Isopropyl-5-methyl-1-2,6-dihydroxy-4-nonylphenylcyclohex-1-ene Aminoalkylindoles AM-630 AM-1241 JWH-015 JWH-018 JWH-073 JWH-081 JWH-200 L-768,242 Pravadoline WIN 55,212-2 Aminoalkylpyrroles JWH-030 JWH-147 JWH-307 Eicosanoids AM-883 Arachidonyl-2'-chloroethylamide Arachidonylcyclopropylamide Methanandamide O-585 O-689 O-1812 O-1860 O-1861 Others BAY 38-7271 BAY 59-3074 GW 842,166X JWH-171 O-2220 Endocannabinoid activity enhancers AM-404 CAY-10401 CAY-10402 N-arachidonoyl-serotonin O-1624 PF-622 PF-750 URB-597 URB-602 URB-754 Cannabinoid antagonists and inverse agonists AM-251 AM-281 AM-630 AVE-1625 BML-190 CAY-10508 CB-25 CB-52 JTE-907 LY-320,135 MK-9470 NESS-0327 O-1184 O-2050 O-2654 Rimonabant SLV-319 SR-144,528 Surinabant Taranabant VCHSR Retrieved from http://en..org/wiki/Pravadoline Categories: Pharmacology stubs | Cannabinoids | Aminoalkylindoles Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page This page was last modified on 4 August 2008, at 02:01
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