# Prodine

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Prodine
> Markdown URL: https://mediated.wiki/source/Prodine.md
> Source: https://en.wikipedia.org/wiki/Prodine
> Source revision: 1333977551
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{short description|Opioid analgesic}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464215177
| IUPAC_name = (1,3-Dimethyl-4-phenylpiperidin-4-yl) propanoate
| image = Prodine.svg
| image_class = skin-invert-image
| width = 180
| caption = Skeletal formula of prodine
| alt = Skeletal formula of prodine
| image2 = Prodine molecule ball.png
| image_class2 = bg-transparent
| width2 = 160
| caption2 = Ball-and-stick model of the alphaprodine molecule
| alt2 = Ball-and-stick model of the alphaprodine molecule

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =  
| 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_UK = <!-- Class A -->
| legal_US = Schedule I
| legal_DE = Anlage I
| legal_status = Rx-only
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =

<!--Identifiers-->
| CAS_supplemental = 
| CAS_number_Ref = {{cascite|correct|CAS}} (alpha)
| CAS_number = 77-20-3
| CAS_number2_Ref = {{cascite|correct|CAS}} (beta)
| CAS_number2 = 468-59-7
| ATC_prefix = none
| ATC_suffix =  
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 14309
| PubChem = 204163
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =  
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 176845
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 001O2254AC
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 21J54X4Z4Z
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D12678
| KEGG2_Ref = {{keggcite|correct|kegg}}
| KEGG2 = D12679

<!--Chemical data-->
| C=16 | H=23 | N=1 | O=2 
| smiles = O=C(CC)O[C@]1(CCN(C[C@H]1C)C)C2=CC=CC=C2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3/t13-,16+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = UVAZQQHAVMNMHE-CJNGLKHVSA-N
| synonyms =  
}}

'''Prodine'''<ref>US Patent 2498433 '1,3 dimethyl-4-propionoxy-4-phenyl-piperidine and acid addition salts thereof'</ref> (trade names '''Prisilidine''' and '''Nisentil''') is an [opioid](/source/opioid) [analgesic](/source/analgesic) that is an [analog](/source/structural_analog) of [pethidine](/source/pethidine) (meperidine).  It was developed in Germany in the late 1940s.

There are two [isomer](/source/isomer)s of the trans form of prodine, alphaprodine and betaprodine.  Both exhibit optical isomerism and alphaprodine and betaprodine are [racemate](/source/racemate)s.<ref name=Reynolds>{{Cite book | vauthors = Reynolds AK, Randall LO | title = Morphine & Allied Drugs | date = 1957 | pages = 310–312 | publisher = University of Toronto Press | oclc = 1628783 }}</ref>  Alphaprodine is closely related to [desomorphine](/source/desomorphine) in steric configuration.<ref name=Reynolds/> The cis form also has active isomers but none are used in medicine.<ref name=Reynolds/><ref>{{cite journal |vauthors=Beckett AH, Walker J | title = The configuration of alphaprodine and betaprodine | journal = Journal of Pharmacy and Pharmacology | year = 1955 | volume = 7 | issue = 1 | pages = 1039–1045 | doi = 10.1111/j.2042-7158.1955.tb12115.x | pmid = 13278850| s2cid = 46012276 }}</ref> Betaprodine is around five times more potent than alphaprodine<ref>{{cite book | vauthors = Stenlake JB | title = Foundations of Molecular Pharmacology | year = 1979 | isbn = 978-0-485-11171-2}}</ref> but is metabolized more rapidly, and only alphaprodine was developed for medicinal use. It has similar activity to pethidine, but with a more rapid onset and shorter duration of effects.<ref>{{cite journal |vauthors=Fung DL, Asling JH, Eisele JH, Martucci R | title = A comparison of alphaprodine and meperidine pharmacokinetics | journal = Journal of Clinical Pharmacology | year = 1980 | volume = 20 | issue = 1 | pages = 37–41 | doi = 10.1002/j.1552-4604.1980.tb01664.x | pmid = 7358866| s2cid = 35046059 }}</ref>  Betaprodine produces more [euphoria](/source/euphoria) and side effects than alphaprodine at all dose levels, and it was found that 5 to 10&nbsp;mg of betaprodine is equivalent to 25 to 40&nbsp;mg of alphaprodine.<ref name=Reynolds/>

Testing in rats showed alphaprodine to be 97% the strength of [morphine](/source/morphine) via the [subcutaneous](/source/Subcutaneous_injection) route and 140% the strength of oral [methadone](/source/methadone).<ref name=Reynolds/>  Betaprodine was 550% stronger than morphine SC, the [laevorotatory](/source/laevorotatory) cis isomer was 350% stronger, and the [dextrorotatory](/source/dextrorotatory) cis isomer was 790% stronger.<ref name=Reynolds/>  Betaprodine taken orally was 420% stronger than oral methadone, the cis form was 390% stronger for the laevorotatory and 505% stronger for the dextrorotatory isomers.<ref name=Reynolds/>

:class=skin-invert-image|400px

Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was most commonly used for pain relief during [childbirth](/source/childbirth)<ref>{{cite journal |vauthors=Burnett RG, White CA | title = Alphaprodine for continuous intravenous obstetric analgesia | journal = Obstetrics & Gynecology | year = 1966 | volume = 27 | issue = 4 | pages = 472–477 | doi = 10.1097/00006250-196604000-00003| pmid = 5907367 }}</ref> and [dentistry](/source/dentistry),<ref>{{cite journal |vauthors=Carter WJ, Bogert JA | title = An effective pre-medication procedure for dental patients | journal = Journal of the Missouri Dental Association | year = 1966 | volume = 46 | issue = 6 | pages = 8–9 | pmid = 5221807}}</ref> as well as for some minor surgical procedures.  Alphaprodine has a duration of action of 1 to 2 hours, and 40 to 60&nbsp;mg is equivalent to 10&nbsp;mg of subcutaneous morphine.

Prodine has broadly similar effects to other opioids, producing [analgesia](/source/analgesia), [sedation](/source/sedation) and euphoria. Side effects can include excessive [itching](/source/itching), [nausea](/source/nausea), [vomiting](/source/vomiting) and potentially serious [respiratory depression](/source/respiratory_depression) which can lead to life-threatening [respiratory arrest](/source/respiratory_arrest). Respiratory depression can be a problem with alphaprodine even at normal therapeutic doses.<ref>{{cite journal |vauthors=Fuller JD, Crombleholme WR | title = Respiratory arrest and prolonged respiratory depression after one low, subcutaneous dose of alphaprodine for obstetric analgesia. A case report | journal = Journal of Reproductive Medicine | year = 1987 | volume = 32 | issue = 2 | pages = 149–151 | pmid = 3560080}}</ref> Unlike pethidine, prodine does not produce toxic metabolites and is therefore more suitable for high-dose therapy.{{medcn|date=September 2013}}

==Regulation==
Alphaprodine has a DEA ACSCN of 9010 and 2013 manufacturing quota of 3 grams; betaprodine has an ACSCN of 9611 and a 2 grams quota.

==See also==
* [Proheptazine](/source/Proheptazine)
* [Trimeperidine](/source/Trimeperidine)

== References ==
{{Reflist|2}}

{{Opioidergics}}

Category:Mu-opioid receptor agonists
Category:Opioids
Category:4-Phenylpiperidines
Category:Propionate esters

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