Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Prodine: Difference between pages

{{short description|Opioid analgesic}}

| Watchedfields = changed

| verifiedrevid = 464215177

| IUPAC_name = (1,3-Dimethyl-4-phenylpiperidin-4-yl) propanoate

| width = 180

| alt = Skeletal formula of prodine

| image2 = Prodine molecule ball.png

| width2 = 160

| alt2 = Ball-and-stick model of the prodine molecule

| 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]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_US = Schedule I

| legal_DE = Anlage I

| legal_status = Rx-only

| routes_of_administration =

| excretion =

| 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

| 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

| smiles = O=C(CC)O[C@]1(CCN(C[C@H]1C)C)C2=CC=CC=C2

'''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]] [[analgesic]] that is an [[structural analog|analog]] of [[pethidine]] (meperidine). It was developed in Germany in the late 1940s.

There are two [[isomer]]s of the trans form of prodine, alphaprodine and betaprodine. Both exhibit optical isomerism and alphaprodine and betaprodine are [[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]] 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]] 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]] via the [[Subcutaneous injection|subcutaneous]] route and 140% the strength of oral [[methadone]].<ref name=Reynolds/> Betaprodine was 550% stronger than morphine SC, the [[laevorotatory]] cis isomer was 350% stronger, and the [[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/>

[[Image:Prodine isomers.png|400px]]

Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was most commonly used for pain relief during [[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]],<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]], [[sedation]] and euphoria. Side effects can include excessive [[itching]], [[nausea]], [[vomiting]] and potentially serious [[respiratory depression]] which can lead to life-threatening [[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]]

* [[Trimeperidine]]

== References ==

{{Reflist|2}}

{{Opioidergics}}

[[Category:Mu-opioid receptor agonists]]

[[Category:Opioids]]

[[Category:4-Phenylpiperidines]]

[[Category:Propionate esters]]