Chemistry:Phenazocine
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| Other names | Fenazocina, Phenazocinum, DEA No. 9715 |
| Routes of administration | Oral |
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| Formula | C22H27NO |
| Molar mass | 321.464 g·mol−1 |
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Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.[1]
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.[2] 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.[3] 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.[4]
Regarding the two enantiomers of phenazocine, (R)-phenazocine[clarification needed] has twenty times the potency of morphine as an analgesic,[5] while (S)-phenazocine has about four times the potency of morphine.[6][full citation needed]
History
Phenazocine was invented in the 1950s.[7][8] 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.[9]
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.[10]
See also
- Tapentadol - An opioid analgesic with reduced abuse-liability
References
- ↑ "Iso-benzmorphan derivatives" US patent 2959594
- ↑ "Some Narcotic Antagonists in the Benzomorphan Series". Journal of Pharmacology and Experimental Therapeutics 143: 141–8. February 1964. PMID 14163985.
- ↑ "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. November 1976. doi:10.1073/pnas.73.11.4215. PMID 186791. Bibcode: 1976PNAS...73.4215F.
- ↑ 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. PMID 4929685.
- ↑ Clarke, E. G. C. (August 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature 184 (4684): 451. doi:10.1038/184451a0. PMID 13810504. Bibcode: 1959Natur.184..451C.
- ↑ Textbook of Pharmacology - Page 117
- ↑ Clarke EG (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature 184 (Suppl 7): 451. doi:10.1038/184451a0. PMID 13810504. Bibcode: 1959Natur.184..451C.
- ↑ Eckenhoff JE (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology 20 (3): 355–8. doi:10.1097/00000542-195905000-00016. PMID 13650222.
- ↑ "Monthly Release Terming and Coding Newsletter". NHS Information Authority. February 2001. http://www.connectingforhealth.nhs.uk/systemsandservices/data/readcodes/docs/tandc0201.pdf.
- ↑ "Quotas - 2013". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm.
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