Phenazocine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Phenazocine
Phenazocine2DCSD.svg
Systematic (IUPAC) name
(2R,6R,11R)-6,11-Dimethyl-3-(2-phenylethyl)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
Clinical data
Legal status Prohibited (S9) (AU) Class A, Withdrawn (UK) Schedule II (US)
Routes Oral
Identifiers
CAS number 127-35-5 N
ATC code N02AD02
PubChem CID 14707
ChemSpider 14031 YesY
UNII J0ND6N0AQC YesY
ChEMBL CHEMBL46399 YesY
Synonyms Fenazocina, Phenazocinum, DEA No. 9715
Chemical data
Formula C22H27NO 
Mol. mass 321.45588 g/mol
 N (what is this?)  (verify)

Phenazocine (brand names Prinadol, Narphen) is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.

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.[1]

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.[2]

Consequently phenazocine is some 4x the potency of morphine as an analgesic. 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.[3]

History[edit]

Phenazocine was invented in the 1950s.[4][5] 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.[6]

Phenazocine was briefly used in the United States but fell out of favour for the above-mentioned reasons;[which?][citation needed] it remains a Schedule II substance under the Comprehensive Drug Abuse Control & Prevention Act (aka Controlled Substances Act) of 1970 (CSA) but is not manufactured; other Schedule II narcotics not in use in the United States include bezitramide and metopon. The DEA ACSCN for phenazocine is 9715 and its 2013 annual manufacturing quota was 6 grammes [7]

References[edit]

  1. ^ Harris LS, Pierson AK (February 1964). "Some Narcotic Antagonists in the Benzomorphan Series". Journal of Pharmacology and Experimental Therapeutics 143: 141–8. PMID 14163985. 
  2. ^ 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. doi:10.1073/pnas.73.11.4215. PMC 431391. PMID 186791. 
  3. ^ 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. 
  4. ^ Clarke EG (August 8, 1959). "Identification of Phenazocine, a Potent New Analgesic". Nature 184 (Suppl 7): 451–451. doi:10.1038/184451a0. PMID 13810504. 
  5. ^ Eckenhoff JE (May–June 1959). "Phenazocine, a new benzomorphan narcotic analgesic". Anesthesiology 20 (3): 355–8. doi:10.1097/00000542-195905000-00016. PMID 13650222. 
  6. ^ "Monthly Release Terming and Coding Newsletter" (PDF). NHS Information Authority. February 2001. Retrieved 2008-01-11. [dead link]
  7. ^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm