Ocfentanil

Ocfentanil
Systematic (IUPAC) name
N-(2-fluorophenyl)-2-methoxy-N-[1-(2-phenylethyl)piperidin-4-yl]acetamide
Clinical data
Identifiers
101343-69-5 Yes
None
PubChem CID 60575
ChemSpider 54604 
UNII MX52WBC8EV Yes
Synonyms Ocfentanyl, A-3217
Chemical data
Formula C22H27FN2O2
370.460 g/mol
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Ocfentanil (INN) (also called A-3217) is a potent synthetic opioid structurally related to fentanyl[1] that was developed in the early 1990s as one of a series of potent naloxone-reversible opioids in an attempt to obtain an opioid that had better therapeutic indices in terms of cardiovascular effects and respiratory depression as compared to fentanyl.[2]

Study of the analgesic activity of ocfentanil using the mouse hot plate test (55 °C) gave an ED50 of 0.007 mg/kg compared to 0.018 mg/kg for fentanyl; ocfentanil being approximately 2.5 times as potent as fentanyl in this test.[3]

In human volunteers ocfentanil induces effective analgesia at 1 μg/kg, while in doses up to 3 μg/kg, analgesia and respiratory depression occurred in a dose-dependent manner. While a further study suggests that ocfentanil may be as effective as morphine in post-operative relief,[4] Ocfentanil was also studied as a supplement to general anaesthesia, in which the researchers concluded that it appears to be similar in action to fentanyl, with 3 μg/kg of ocfentanil approximately equivalent to 5 μg/kg of fentanyl.[5][6]

Side effects of fentanyl analogues are similar to those of fentanyl, and include itching, nausea and potentially serious respiratory depression which can be life-threatening.

Synthesis

Ocfentanil synthesis: U.S. Patent 4,584,303

References

  1. ↑ Filer CN (1995). "The synthesis of [fluorophenyl-3H(N)] ocfentanil and [fluorophenyl-3H(N)] brifentanil.". Journal of Labelled Compounds and Radiopharmaceuticals 36 (11): 1019–27.
  2. ↑ US Patent application 2002/176888 A1
  3. ↑ Bagley J. R. (1991). "Evolution of the 4-Anilidopiperidine Class of Opioid Analgesics.". Medicinal Research Reviews 11 (4): 403–436.
  4. ↑ Glass P (1989). "The analgesic efficacy of A3217". Anesthesiology (71).
  5. ↑ Fletcher JE, Sebel PS, Murphy MR, Mick SA, Fein S. Comparison of ocfentanil and fentanyl as supplements to general anesthesia. Anesthesia and Analgesia. 1991 Nov;73(5):622-6. PMID 1952145
  6. ↑ Ebrahim Z (1991). "Multiple dose evaluation of the efficacy of ocfentanil hydrochloride (A3217) to produce postoperative analgesia.". Anesthesia and Analgesia 72.