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Picenadol


Picenadol
Systematic (IUPAC) name
3-(1,3-dimethyl-4-propylpiperidin-4-yl)phenol
Identifiers
CAS number	79201-85-7
ATC code	?
PubChem	53077
Chemical data
Formula	C₁₆H₂₅N O
Mol. mass	247.38 g/mol
Synonyms	Picenadol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Picenadol (LY-150720) is a 4-phenylpiperidine derivative that is an opioid analgesic drug.

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Picenadol is an effective analgesic with similar efficacy to pethidine (meperidine). It has been investigated for some applications such as obstetrics^[1] and dentistry,^[2] but never commercialised.

It is unusual in that one enantiomer is a pure μ-opioid agonist, while the other is an antagonist.^[3] The (3R,4R) isomer is the agonist, while (3S,4S) is antagonist.^[4] This means that the racemic mix of the two enantiomers is a mixed agonist-antagonist, with relatively low abuse potential, and little of the κ-opioid activity that tends to cause problems with other opioid mixed agonist-antagonists such as pentazocine.^[5]

References

^ Sherline DM. Picenadol (LY 150720) compared with meperidine and placebo for relief of post-cesarean section pain: a randomized double-blind study. American Journal of Obstetrics and Gynecology. 1983 Oct 15;147(4):404-6.
^ Goldstein DJ, Brunelle RL, George RE, Cooper SA, Desjardins PJ, Gaston GW, Jeffers GE, Gallegos LT, Reynolds DC. Picenadol in a large multicenter dental pain study. Pharmacotherapy. 1994 Jan-Feb;14(1):54-9.
^ Leander JD, Zimmerman DM. Effects of picenadol and its agonist and antagonist isomers on schedule-controlled behavior. Journal of Pharmacology and Experimental Therapeutics. 1983 Dec;227(3):671-5.
^ Froimowitz M, Cody V. Absolute configurations and conformations of the opioid agonist and antagonist enantiomers of picenadol. Chirality. 1995;7(7):518-25.
^ Zimmerman DM, Smits SE, Hynes MD, Cantrell BE, Leander JD, Mendelsohn LG, Nickander R. Picenadol. Drug and Alcohol Dependence. 1985 Feb;14(3-4):381-401.

v • d • e

Opioids

Opiate derivatives

6-Methyldihydromorphine • 6-Methylenedihydrodesoxymorphine • 14-Methoxymetopon • Acetylcodeine • Acetyldihydrocodeine • Acetyldihydrocodeinone • Acetylmorphone • Benzylmorphine • β-4-morpholinylethylmorphine • Codeine • Codeine-N-Oxide • Codeinone • Codoxime • Desomorphine • Diacetyldihydromorphine • Dihydrocodeine • Dihydrocodeinone enol acetate • Dihydrohydroxycodeinone • Dihydrodesoxymorphine • Dihydroheroin • Dihydroisocodeine • Dihydromorphine • Dipropanoylmorphine • Ethylmorphine • Heroin (Diamorphine) • Heterocodeine • Hydrocodone • Hydromorphinol • Hydromorphone • Laudanum • Methyldesorphine • Methyldihydromorphine • Methylnaltrexone • Metopon • Monoacetylmorphine • Morphine-N-Oxide • Morphine • Morphinone • Morphine-6-glucuronide • Myrophine • Nalbuphine • Nalmefene • Nalorphine • Naloxone • Naltrexone • Naltrindole • Nicocodeine • Nicodicodeine • Nicomorphine • Norcodeine • Normorphine • Omnopon • Opium • Oripavine • Oxycodone • Oxymorphone • Pantopon • Papaveretum • Paregoric • Pholcodeine • Pseudomorphine • Poppy Straw • Poppy Tea • Semorphone • Tetrapon • Thebacon • Thebaine

Morphinans

Butorphanol • Cyclorphan • Dextro-3-hydroxy-N-allylmorphinan • Dextrorphan • Drotebanol • Levargorphan • Levallorphan • Levorphanol • Levorphan • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Racemethorphan • Racemorphan

Benzomorphans

Bremazocine • Cyclazocine • Dezocine • Ethylketocyclazocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine • WIN-7681
Prodines	Allylprodine • α-meprodine • α-prodine • β-meprodine • β-prodine • Meprodine • MPPP • PEPAP • Prodine • Prosidol • Trimeperidine
Ketobemidones	Acetoxyketobemidone • Ketobemidone • Methylketobemidone • Propylketobemidone
Others	Alvimopan • Loperamide • Picenadol

Open Chain Opioids

Amidones	Dextromethadone • Dipipanone • Isomethadone • Levomethadone • Methadone • Methadone Intermediate • Norpipanone • Phenadoxone (Heptazone) • Pipidone
Methadols	Acetylmethadol • α-methadol • α-acetylmethadol • β-methadol • β-acetylmethadol • Dimepheptanol • Levo-α-acetylmethadol • Noracymethadol
Moramides	Dextromoramide • Levomoramide • Moramide Intermediate • Racemoramide
Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene
Phenalkoxams	Dextropropoxyphene • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Propoxyphene
Ampromides	Diampromide • Phenampromide • Propiram
Others	Lefetamine