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| Routes of administration | Intravenous |
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| Pharmacokinetic data | |
| Metabolism | Liver |
| Excretion | Bile andUrine |
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| ECHA InfoCard | 100.008.391 |
| Chemical and physical data | |
| Formula | C23H29NO3 |
| Molar mass | 367.489 g·mol−1 |
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Phenoperidine[2][3] (Operidine orLealgin), is anopioidanalgesic which is structurally related topethidine and is used clinically as ageneral anesthetic.
Phenoperidine is anopioid pain killer—anarcotic analgesic.[medical citation needed]
It is a derivative ofisonipecotic acid, likepethidine, and is metabolized in part tonorpethidine. Its potency range is due to method of ingestion. figure 20–80 times as potent as pethidine as ananalgesic. The greatly increased potency essentially eliminates the toxic effects of norpethidine accumulation which are seen when pethidine is administered in high doses or for long periods of time.[4]
Phenoperidine was first synthesized in 1957 byPaul Janssen, of the company now known asJanssen Pharmaceutica, who was seeking betteropioid pain-killers.[5] His two prototype drugs weremethadone andpethidine, each which had been invented in 1930s by Otto Eisleb, who worked forIG Farben. His initial work starting with methadone yieldeddextromoramide in 1954. Janssen then turned to making pethidine analogues, due in part to the less complicated chemistry of the compound. During his explorations, he replaced the methyl group attached to the pethidine nitrogen with a phenylhydroxypropyl group, and this yielded phenoperidine, in 1957. Phenoperidine was determined to have decreased stability and enhanced lipophilicity compared to pethidine. Soon after, studies in mice showed that phenoperidine was over 100 times more potent than pethidine.[5]
In 1958, the same line of work yielded "one of the greatest advances of the 20th century psychiatry",haloperidol,[5] as well asdiphenoxylate, which lacked the opioid's analgesic properties but still stoppedperistalsis in the intestines, a typical side effect of opioids; Janssen brought diphenoxylate to market as a drug to treat diarrhea.[6]: 124 And through further advances, Janssen createdfentanyl in 1960, which proved to be ten times more potent than phenoperidine.[7]
In 1959, the combination of phenoperidine andhaloperidol was first used in Europe inanesthesia to induce a detached, pain free state calledneuroleptic analgesia; the use of that mixture boomed in early 1960s but was overtaken by the combination offentanyl anddroperidol, which was widely used through the 1980s. These combination approaches were not adopted in the US.[8]: 644
In 1961 phenoperidine was added to the 1931Convention for Limiting the Manufacture and Regulating the Distribution of Narcotic Drugs by theWorld Health Organization via theSingle Convention on Narcotic Drugs.[9][10]
In the US it is classified as aDrug Enforcement Administration (DEA) Schedule I controlled substance opiate with a corresponding code 9641.[11]