Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.[2]
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| Other names | Fenazocina, Phenazocinum, DEA No. 9715 |
| Routes of administration | Oral |
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| ECHA InfoCard | 100.004.397 |
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| Formula | C22H27NO |
| Molar mass | 321.464 g·mol−1 |
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Effects of phenazocine include analgesia and euphoria, also may include dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors.[3] Phenazocine appears to be a much stronger analgesic with fewer side effects than pentazocine, probably due to a more favorable μ/κ binding ratio. Phenazocine is a much more potent analgesic than pentazocine and other drugs in the benzomorphan series, most probably due to the presence of an N-phenethyl substitution, which is known to boost μ-opioid activity in many classes of opioid analgesics.[4] Also, it does not cause spasm of the sphincter of Oddi, making it more suitable than morphine for the treatment of biliary or pancreatic pain.[5]
Regarding the two enantiomers of phenazocine, (R)-phenazocine[clarification needed] has twenty times the potency of morphine as an analgesic,[6] while (S)-phenazocine has about four times the potency of morphine.[7][full citation needed]
History
editPhenazocine was invented in the 1950s.[8][9] It was one of a number of benzomorphan opioids (including pentazocine, dezocine, and cyclazocine) developed in the search for non-addictive strong analgesics.
Phenazocine was once widely used, and was mainly supplied as 5 mg tablets of the hydrobromide salt for sublingual use (Narphen, Prinadol and other names), but its use was discontinued in the United Kingdom in 2001.[10]
Phenazocine was briefly used in the United States but fell out of favor;[citation needed] it remains a Schedule II substance under the Comprehensive Drug Abuse Control & Prevention Act (Controlled Substances Act) of 1970 (CSA) but is not manufactured. The DEA ACSCN for phenazocine is 9715 and its 2013 annual manufacturing quota was 6 grams.[11]
See also
edit- Tapentadol - An opioid analgesic with reduced abuse-liability
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). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
- ^ US 2959594, "Iso-benzmorphan derivatives"
- ^ Harris LS, Pierson AK (February 1964). "Some Narcotic Antagonists in the Benzomorphan Series". Journal of Pharmacology and Experimental Therapeutics. 143: 141–8. PMID 14163985.
- ^ Feinberg AP, Creese I, Snyder SH (November 1976). "The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists". Proceedings of the National Academy of Sciences USA. 73 (11): 4215–9. Bibcode:1976PNAS...73.4215F. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791.
- ^ Hopton D. (January 1971). "Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain". Gut. 12 (1): 51–4. doi:10.1136/gut.12.1.51. PMC 1411461. PMID 4929685.
- ^ Clarke, E. G. C. (August 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature. 184 (4684): 451. Bibcode:1959Natur.184..451C. doi:10.1038/184451a0. PMID 13810504. S2CID 4190489.
- ^ Textbook of Pharmacology - Page 117
- ^ Clarke EG (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature. 184 (Suppl 7): 451. Bibcode:1959Natur.184..451C. doi:10.1038/184451a0. PMID 13810504. S2CID 4190489.
- ^ Eckenhoff JE (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology. 20 (3): 355–8. doi:10.1097/00000542-195905000-00016. PMID 13650222. S2CID 30670011.
- ^ "Monthly Release Terming and Coding Newsletter" (PDF). NHS Information Authority. February 2001. Archived from the original (PDF) on 2008-11-06. Retrieved 2008-01-11.
- ^ "Quotas - 2013". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.