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Phenazocine



Phenazocine
Systematic (IUPAC) name
1,2,3,4,5,6-hexahydro-6,11-dimethyl-3- (2-phenylethyl)-2,6-Methano-3-benzazocin-8-ol
Identifiers
CAS number 127-35-5
ATC code  ?
PubChem 14707
Chemical data
Formula C22H27NO 
Mol. mass 321.46 g/mol
Synonyms Phenazocine, Prinadol, Narphen
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

Phenazocine (Prinadol, Narphen) is an opioid analgesic, invented in the 1950s,[1][2] which is related to pentazocine and has a similar profile of effects that include analgesic action and euphoria, but may produce dysphoria and hallucinations at high doses, most likely due to action at κ-opioid and σ receptors.[3] However phenazocine appears to be a much stronger analgesic and with less side effects than pentazocine, probably reflecting a more favourable μ/κ binding ratio. Phenazocine used to be widely used in medicine, mainly supplied as 5mg tablets of the hydrobromide salt, but was discontinued in 2001 and is now no longer used.[1]

Additional recommended knowledge

Phenazocine is much more potent as an 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] 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.[5]




References

  1. ^ Clarke EGC. Identification of Phenazocine, a Potent New Analgesic. Nature. 1959; 184: 451.
  2. ^ Eckenhoff JE. Phenazocine, a new benzomorphan narcotic analgesic. Anesthesiology. 1959 May-Jun;20(3):355-8.
  3. ^ Harris LS, Pierson AK. Some Narcotic Antagonists in the Benzomorphan Series. Journal of Pharmacology and Experimental Therapeutics. 1964 Feb;143:141-8.
  4. ^ Feinberg AP, Creese I, Snyder SH. The opiate receptor: a model explaining structure-activity relationships of opiate agonists and antagonists. Proceedings of the National Academy of Sciences U S A. 1976 Nov;73(11):4215-9.
  5. ^ Hopton D. Double-blind clinical trial of the analgesic effects of phenazocine hydrobromide (Narphen) compared with morphine sulphate in patients with acute abdominal pain. Gut. 1971 Jan;12(1):51-4.


 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Phenazocine". A list of authors is available in Wikipedia.
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