Piritramide

{{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

| width2 = 230px

| 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 = {{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 |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule I

| legal_DE = Anlage III

| legal_US = Schedule I

| routes_of_administration = Oral, IM, IV

| bioavailability =

| protein_bound = 95%{{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 }}

| metabolism = Liver

| elimination_half-life = 4-10 hours (acute dosing), 17.4 hours (chronic dosing)

| excretion =

| 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 =

| 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

| 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 US Patent 3080366 (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, Slovenia, Germany and the Netherlands.{{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}} 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.{{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 }} Nausea, vomiting, respiratory depression and constipation are believed to be less frequent with piritramide than with 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. After intravenous administration the onset of analgesia is as little as 1–2 minutes, which may be related to its great lipophilicity.{{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}} The analgesic and sedative effects of piritramide are believed to be potentiated with phenothiazines and its emetic (nausea/vomiting-inducing) effects are suppressed. 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.

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 (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.{{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 }}