Prodine
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| Formula | C16H23NO2 |
| Molar mass | 261.365g·mol−1 |
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Prodine[2](trade namesPrisilidineandNisentil) is anopioidanalgesicthat is ananalogofpethidine(meperidine). It was developed in Germany in the late 1940s.
There are twoisomersof the trans form of prodine, Alpha prodine and betaprodine. Both exhibit optical isomerism and Alpha prodine and betaprodine areracemates.[3]Alphaprodine is closely related todesomorphinein steric configuration.[3]The cis form also has active isomers but none are used in medicine.[3][4]Betaprodine is around five times more potent than Alpha prodine[5]but is metabolized more rapidly, and only Alpha prodine was developed for medicinal use. It has similar activity to pethidine, but with a more rapid onset and shorter duration of effects.[6]Betaprodine produces moreeuphoriaand side effects than Alpha prodine at all dose levels, and it was found that 5 to 10 mg of betaprodine is equivalent to 25 to 40 mg of Alpha prodine.[3]
Testing in rats showed Alpha prodine to be 97% the strength ofmorphinevia thesubcutaneousroute and 140% the strength of oralmethadone.[3]Betaprodine was 550% stronger than morphine SC, thelaevorotatorycis isomer was 350% stronger, and thedextrorotatorycis isomer was 790% stronger.[3]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.[3]
Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was most commonly used for pain relief duringchildbirth[7]anddentistry,[8]as well as for some minor surgical procedures. Alphaprodine has a duration of action of 1 to 2 hours, and 40 to 60 mg is equivalent to 10 mg of subcutaneous morphine.
Prodine has broadly similar effects to other opioids, producinganalgesia,sedationand euphoria. Side effects can include excessiveitching,nausea,vomitingand potentially seriousrespiratory depressionwhich can lead to life-threateningrespiratory arrest.Respiratory depression can be a problem with Alpha prodine even at normal therapeutic doses.[9]Unlike pethidine, prodine does not produce toxic metabolites and is therefore more suitable for high-dose therapy.[medical citation needed]
Regulation
[edit]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
[edit]References
[edit]- ^Anvisa(2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 2023-04-04).Archivedfrom the original on 2023-08-03.Retrieved2023-08-16.
- ^US Patent 2498433 '1,3 dimethyl-4-propionoxy-4-phenyl-piperidine and acid addition salts thereof'
- ^abcdefgReynolds AK, Randall LO (1957).Morphine & Allied Drugs.University of Toronto Press. pp. 310–312.OCLC1628783.
- ^Beckett AH, Walker J (1955). "The configuration of Alpha prodine and betaprodine".Journal of Pharmacy and Pharmacology.7(1): 1039–1045.doi:10.1111/j.2042-7158.1955.tb12115.x.PMID13278850.S2CID46012276.
- ^Stenlake JB (1979).Foundations of Molecular Pharmacology.ISBN978-0-485-11171-2.
- ^Fung DL, Asling JH, Eisele JH, Martucci R (1980). "A comparison of Alpha prodine and meperidine pharmacokinetics".Journal of Clinical Pharmacology.20(1): 37–41.doi:10.1002/j.1552-4604.1980.tb01664.x.PMID7358866.S2CID35046059.
- ^Burnett RG, White CA (1966). "Alphaprodine for continuous intravenous obstetric analgesia".Obstetrics & Gynecology.27(4): 472–477.doi:10.1097/00006250-196604000-00003.PMID5907367.
- ^Carter WJ, Bogert JA (1966). "An effective pre-medication procedure for dental patients".Journal of the Missouri Dental Association.46(6): 8–9.PMID5221807.
- ^Fuller JD, Crombleholme WR (1987). "Respiratory arrest and prolonged respiratory depression after one low, subcutaneous dose of Alpha prodine for obstetric analgesia. A case report".Journal of Reproductive Medicine.32(2): 149–151.PMID3560080.