Phenoperidine

Phenoperidine

Clinical data
Routes of administration	Intravenous
ATC code	N01AH04 (WHO)
Legal status
Legal status	AU: S8 (Controlled drug) US: Schedule I
Pharmacokinetic data
Metabolism	Liver
Excretion	Bile and Urine
Identifiers
IUPAC name ethyl 1-(3-hydroxy-3-phenylpropyl)-4-phenylpiperidine-4-carboxylate
CAS Number	562-26-5 N
PubChem CID	11226
ChemSpider	10752 Y
UNII	G9BH09J4JW
KEGG	D02611 Y
CompTox Dashboard (EPA)	DTXSID90862199
ECHA InfoCard	100.008.391
Chemical and physical data
Formula	C23H29NO3
Molar mass	367.481 g·mol−1
3D model (JSmol)	Interactive image
SMILES OC(C1=CC=CC=C1)CCN(CC2)CCC2(C3=CC=CC=C3)OC(CC)=O
InChI InChI=1S/C23H29NO3/c1-2-27-22(26)23(20-11-7-4-8-12-20)14-17-24(18-15-23)16-13-21(25)19-9-5-3-6-10-19/h3-12,21,25H,2,13-18H2,1H3 Y Key:IPOPQVVNCFQFRK-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Phenoperidine was discovered by Janssen Pharmaceutica 1960. 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.

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.

Opioid Market

In 2011, the total global morphine equivalent opioid consumption per person was 61.66 mg/capita. While in the Americas, the total morphine equivalent opioid consumption was roughly 750 mg/capita.

External links

• 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
• Claris, O.; Bertrix, L. (1988). "Phenoperidine: Pharmacology and Use in Pediatric Resuscitation". Pédiatrie (in French). 43 (6): 509–513. PMID 3186421.{{cite journal}}: CS1 maint: multiple names: authors list (link)
• "Antipsychotics - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories, Kyoto University, University of Tokyo. Retrieved 2007-01-16.