# Piritramide

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Piritramide
> Markdown URL: https://mediated.wiki/source/Piritramide.md
> Source: https://en.wikipedia.org/wiki/Piritramide
> Source revision: 1346821767
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Short description|Synthetic opioid}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464207919
| IUPAC_name = 1-(3-cyano-3,3-diphenylpropyl)-4-(piperidin-1-yl)piperidine-4-carboxamide
| image = Piritramide2DACS.svg
| image_class = skin-invert-image
| width = 130px
| image2 = Piritramide-xtal-1977-ball-and-stick.png
| image_class2 = bg-transparent
| width2 = 230px

<!--Clinical data-->| tradename = Dipidolor
| Drugs.com = {{drugs.com|international|piritramide}}
| pregnancy_AU = 
| pregnancy_US = 
| pregnancy_category = No teratogenic effects in preclinical studies; but, as with other opioids it may cause reversible adverse effects in the newborn.
| legal_AU = S8
| legal_BR = A1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[Diário Oficial da União](/source/Di%C3%A1rio_Oficial_da_Uni%C3%A3o) |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_DE = Anlage III
| legal_US = Schedule I
| routes_of_administration = Oral, [IM](/source/Intramuscular_injection), [IV](/source/Intravenous_therapy)

<!--Pharmacokinetic data-->| bioavailability = 
| protein_bound = 95%<ref name = deranaes>{{cite journal | vauthors = Jage J, Laufenberg-Feldmann R, Heid F | title = [Drugs for postoperative analgesia: routine and new aspects: Part 2: opioids, ketamine and gabapentinoids] | language = German | journal = Der Anaesthesist | volume = 57 | issue = 5 | pages = 491–8 | date = May 2008 | pmid = 18409073 | doi = 10.1007/s00101-008-1327-9 | s2cid = 195690966 | trans-title = Drugs for postoperative analgesia: routine and new aspects: Part 2: opioids, ketamine and gabapentinoids }}</ref>
| metabolism = Liver
| elimination_half-life = 4-10 hours (acute dosing), 17.4 hours (chronic dosing)
| excretion = <!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 302-41-0
| ATC_prefix = N02
| ATC_suffix = AC03
| ATC_supplemental = 
| PubChem = 9331
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB12492
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8967
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4RP92LYZ2F
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07288
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 559288

<!--Chemical data-->| C = 27
| H = 34
| N = 4
| O = 1
| smiles = N#CC(C1=CC=CC=C1)(CCN2CCC(N3CCCCC3)(CC2)C(N)=O)C4=CC=CC=C4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C27H34N4O/c28-22-26(23-10-4-1-5-11-23,24-12-6-2-7-13-24)14-19-30-20-15-27(16-21-30,25(29)32)31-17-8-3-9-18-31/h1-2,4-7,10-13H,3,8-9,14-21H2,(H2,29,32)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IHEHEFLXQFOQJO-UHFFFAOYSA-N
}}

'''Piritramide'''<ref> US Patent 3080366</ref> ('''R-3365''', trade names '''Dipidolor''', '''Piridolan''', '''Pirium''' and others) is a synthetic [opioid](/source/opioid) [analgesic](/source/analgesic) (narcotic painkiller) that is marketed in certain [Europe](/source/Europe)an countries including: [Austria](/source/Austria), [Belgium](/source/Belgium), [Czech Republic](/source/Czech_Republic), [Slovenia](/source/Slovenia),  [Germany](/source/Germany) and the [Netherlands](/source/Netherlands).<ref name = MD>{{cite web|title=Piritramide|work=Martindale: The Complete Drug Reference|publisher=Pharmaceutical Press|access-date=22 April 2014|date=23 September 2011| veditors = Brayfield A |url=http://www.medicinescomplete.com/mc/martindale/current/6259-x.htm}}</ref> It comes in free form, is about 0.75x times as potent as [morphine](/source/morphine) and is given [parenterally](/source/parenterally) (by injection) for the treatment of severe pain.<ref name = MD/><ref>{{cite journal | vauthors = Kay B | title = A clinical investigation of piritramide in the treatment of postoperative pain | journal = British Journal of Anaesthesia | volume = 43 | issue = 12 | pages = 1167–71 | date = December 1971 | pmid = 4945251 | doi = 10.1093/bja/43.12.1167 | s2cid = 17729725 | doi-access = free }}</ref> Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with [morphine](/source/morphine) (the gold standard opioid against which other opioids are compared and contrasted), and it produces more rapid-onset analgesia (pain relief) when compared to morphine and [pethidine](/source/pethidine). After intravenous administration the onset of analgesia is as little as 1–2 minutes, which may be related to its great [lipophilicity](/source/lipophilicity).<ref name = SPC>{{cite web|title=FACHINFORMATION (Zusammenfassung der Merkmale des Arzneimittels)|trans-title=PROFESSIONAL INFORMATION (Summary of Product Characteristics)|work=Janssen|publisher=Janssen - Cilag Pharma GmbH|url=http://www.janssen-medinfo.at/sites/janssen_medinfo_at/themes/medinfo_at/images/Dipidolor_FI_20131206.pdf|access-date=9 April 2014|date=November 2013|archive-date=2 May 2014|archive-url=https://web.archive.org/web/20140502000943/http://www.janssen-medinfo.at/sites/janssen_medinfo_at/themes/medinfo_at/images/Dipidolor_FI_20131206.pdf|url-status=dead}}</ref> The analgesic and sedative effects of piritramide are believed to be potentiated with phenothiazines and its emetic (nausea/vomiting-inducing) effects are suppressed.<ref name = SPC/> The [volume of distribution](/source/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.<ref name = SPC/>

Piritramide was developed and patented in Belgium, at Janssen, in 1960.  It is part of an eponymous two-member class of opioids in clinical use with the other being [bezitramide](/source/bezitramide) (Burgodin).  The closest chemical and structural relatives of piritramide in clinical use include the [diphenoxylate](/source/diphenoxylate) family, [fentanyl](/source/fentanyl) (both Janssen discoveries) and somewhat more distantly [alphaprodine](/source/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.<ref>{{Cite web | url=http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm | title=DEA Diversion Control Division | access-date=2014-05-31 | archive-date=2017-05-14 | archive-url=https://web.archive.org/web/20170514115234/https://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm | url-status=dead }}</ref>
== References ==
{{Reflist|2}}

{{Analgesics}}
{{Opioidergics}}

Category:Opioids
Category:Piperidines
Category:Carboxamides
Category:Nitriles
Category:Mu-opioid receptor agonists
Category:Janssen Pharmaceutica
Category:Belgian inventions

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Adapted from the Wikipedia article [Piritramide](https://en.wikipedia.org/wiki/Piritramide) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Piritramide?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.