Piritramide

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Piritramide
Piritramide2DACS.svg
Piritramide3DanJ2.gif
Systematic (IUPAC) name
1-(3-cyano-3,3-diphenyl-propyl)-4-(1-piperidyl)piperidine-4-carboxamide
Clinical data
Trade names Dipidolor
AHFS/Drugs.com International Drug Names
Pregnancy cat.
  • No teratogenic effects in preclinical studies; but, as with other opioids it may cause reversible adverse effects in the newborn.
Legal status
Routes Oral, IM, IV
Pharmacokinetic data
Protein binding 95%[1]
Metabolism Liver
Half-life 4-10 hours (acute dosing), 17.4 hours (chronic dosing)
Identifiers
CAS number 302-41-0 N
ATC code N02AC03
PubChem CID 9331
ChemSpider 8967 YesY
UNII 4RP92LYZ2F YesY
KEGG D07288 YesY
ChEMBL CHEMBL559288 YesY
Chemical data
Formula C27H34N4O 
Mol. mass 430.585 g/mol
 N (what is this?)  (verify)

Piritramide (R-3365, trade names Dipidolor, Piridolan, Pirium and others) is a synthetic opioid analgesic (narcotic painkiller) that is marketed in certain European countries including: Austria, Belgium, Czech Republic, Germany and the Netherlands.[2] It comes in free form, is about 0.75x times as potent as morphine and is given parenterally (by injection) for the treatment of severe pain.[2][3] Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with morphine (which is the gold standard opioid against which other opioids are compared and contrasted against) and it produces more rapid-onset analgesia (pain relief) when compared to morphine and pethidine, after intravenous administration the onset of analgesia is as little as 1–2 minutes, which may be related to its great lipophilicity.[4] The analgesic and sedative effects of piritramide are believed to be potentiated with phenothiazines and its emetic (nausea/vomiting-inducing) effects are suppressed.[4] The volume of distribution is 0.7-1 L/kg after a single dose, 4.7-6 L/kg after steady-state concentrations are achieved and up to 11.1 L/kg after prolonged dosing.[4]

History & Regulation[edit]

Piritramide was developed and patented in the Netherlands, at Janssen, in 1960. It is part of an eponymous two-member class of opioids in clinical use with the other being bezitramide (Burgodin). The closest chemical and structural relatives of piritramide in clinical use include the diphenoxylate family, fentanyl (both Janssen discoveries) and somewhat more distantly alphaprodine.

Not being in clinical use in the United States, it is a Schedule I Narcotic controlled substance with a DEA ACSCN of 9642 and manufacturing quota of zero.[5] It presumably has abuse potential, and appears on the European black market on occasion and has a handful of street names including "Pierrette" and "P".[6] LEXIS-NEXIS and other database searches do not show mentions of law enforcement contact with this drug in the United States. Piritramide is specifically exempted from the Canadian controlled-substances law, and its relative bezitramide is a Schedule II controlled substance in the US, although not used there as of 2014.

Synthesis[edit]

See also[edit]

References[edit]

  1. ^ Jage, J; Laufenberg-Feldmann, R; Heid, F (May 2008). "Medikamente zur postoperativen Schmerztherapie: Bewährtes und Neues" [Drugs for postoperative analgesia: routine and new aspects: Part 2: opioids, ketamine and gabapentinoids]. Der Anaesthesist (in German) 57 (5): 491–8. doi:10.1007/s00101-008-1327-9. PMID 18409073. 
  2. ^ a b Brayfield, A, ed. (23 September 2011). "Piritramide". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 22 April 2014. 
  3. ^ Kay, B (December 1971). "A clinical investigation of piritramide in the treatment of postoperative pain.". British Journal of Anaesthesia 43 (12): 1167–71. doi:10.1093/bja/43.12.1167. PMID 4945251. 
  4. ^ a b c "FACHINFORMATION (Zusammenfassung der Merkmale des Arzneimittels)" [PROFESSIONAL INFORMATION (Summary of Product Characteristics)] (PDF). Janssen. Janssen - Cilag Pharma GmbH. November 2013. Retrieved 9 April 2014. 
  5. ^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm
  6. ^ Inside Narcotics, 5th Edition, pp 347 (sidebar) "Piritramide -- what they say - Wien 8/iii/2002"