Phenoperidine

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Phenoperidine
Phenoperidine.svg
Systematic (IUPAC) name
ethyl 1-(3-hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylate
Clinical data
Legal status Controlled (S8) (AU) Schedule I (US)
Routes Intravenous
Pharmacokinetic data
Metabolism Liver
Excretion Bile and Urine
Identifiers
CAS number 562-26-5 N
ATC code N01AH04
PubChem CID 11226
ChemSpider 10752 YesY
UNII G9BH09J4JW YesY
KEGG D02611 YesY
Chemical data
Formula C23H29NO3 
Mol. mass 367.481
 N (what is this?)  (verify)

Phenoperidine was discovered by Janssen Pharmaceutica 1960.[1] Marketed as its hydrochloride as Operidine or Lealgin, is an opioid used as a general anesthetic. It is a derivative of isonipecotic acid, like pethidine, and is metabolized in part to norpethidine. It is 20-200 times as potent as pethidine as an analgesic. 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.

In humans 1 milligram is equipotent with 10 mg morphine. It has less effect on the circulatory system and is less hypnotic than morphine, but it has about the same emetic effect. The nausea can be prevented by giving droperidol or haloperidol. After an intravenous dose the analgesia sets in after 3–5 minutes.[2]

Phenoperidine shares structural similarities with both pethidine and haloperidol (and related butyrophenone antipsychotics, e.g. droperidol). While not commonly used today in clinical practice, it is of historical interest as a precursor in the development of some of the most widely used neuroleptic drugs on the market today.

References[edit]

  1. ^ BE Patent 576331
  2. ^ Farmacevtiska specialiteter i Sverige (FASS) (in Swedish). Stockholm: Linfo. 1983. ISBN 91-85314-44-7. 

External links[edit]

  • Kintz, P.; Godelar, B.; Mangin, P.; Lugnier, A.; Chaumont, A. (1989). "Simultaneous Determination of Pethidine (Meperidine), Phenoperidine, and Norpethidine (Normeperidine), their Common Metabolite, by Gas Chromatography with Selective Nitrogen Detection". Forensic Science International 43 (3): 267–273. doi:10.1016/0379-0738(89)90154-0. PMID 2613140. 
  • Claris, O.; Bertrix, L. (1988). "Phenoperidine: Pharmacology and Use in Pediatric Resuscitation". Pédiatrie (in French) 43 (6): 509–513. PMID 3186421. 
  • "Antipsychotics - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories, Kyoto University, University of Tokyo. Retrieved 2007-01-16.