Global InformationOcfentanil information
 | |
 | |
| Clinical data | |
|---|---|
| Other names | Ocfentanyl, A-3217 |
| ATC code |
|
| Legal status | |
| Legal status |
|
| Identifiers | |
IUPAC name
| |
| CAS Number |
|
| PubChem CID |
|
| ChemSpider |
|
| UNII |
|
| CompTox Dashboard (EPA) |
|
| Chemical and physical data | |
| Formula | C22H27FN2O2 |
| Molar mass | 370.468 g·mol−1 |
| 3D model (JSmol) |
|
SMILES
| |
InChI
| |
  (what is this?) (verify) | |
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] Ocfentanil was never developed for medical use despite reasonable results in human clinical trials, but subsequently started to be sold as a designer drug starting in around 2013.[3]
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.[4]
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,[5] 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.[6][7]
Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear.[8][9]
- ^ Filer CN, Nugent RP, Huang BS (November 1995). "The synthesis of [fluorophenyl-3H(N)] ocfentanil and [fluorophenyl-3H(N)] brifentanil". Journal of Labelled Compounds and Radiopharmaceuticals. 36 (11): 1019–1027. doi:10.1002/jlcr.2580361102. ISSN 1099-1344.
- ^ US 2002176888, "Oral dosage forms"
- ^ Misailidi N, Papoutsis I, Nikolaou P, Dona A, Spiliopoulou C, Athanaselis S (January 2018). "Fentanyls continue to replace heroin in the drug arena: the cases of ocfentanil and carfentanil". Forensic Toxicology. 36 (1): 12–32. doi:10.1007/s11419-017-0379-4. PMC 5754389. PMID 29367860.
- ^ Bagley JR, Kudzma LV, Lalinde NL, Colapret JA, Huang BS, Lin BS, et al. (July 1991). "Evolution of the 4-anilidopiperidine class of opioid analgesics". Medicinal Research Reviews. 11 (4): 403–36. doi:10.1002/med.2610110404. PMID 1875771. S2CID 33000913.
- ^ Glass P, Camporesi E, Martel D, Afifi M (1989). "The Analgesic Efficacy of A3217". Anesthesiology. 71 (Supplement): A321. doi:10.1097/00000542-198909001-00321.
- ^ Fletcher JE, Sebel PS, Murphy MR, Mick SA, Fein S (November 1991). "Comparison of ocfentanil and fentanyl as supplements to general anesthesia". Anesthesia and Analgesia. 73 (5): 622–6. doi:10.1213/00000539-199111000-00019. PMID 1952145. S2CID 40909537.
- ^ Ebrahim Z (1991). "Multiple dose evaluation of the efficacy of ocfentanil hydrochloride (A3217) to produce postoperative analgesia". Anesthesia and Analgesia. 72: S63. doi:10.1213/00000539-199102001-00001.
- ^ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy. 26 (7): 626–31. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
- ^ Dussy FE, Hangartner S, Hamberg C, Berchtold C, Scherer U, Schlotterbeck G, et al. (November 2016). "An Acute Ocfentanil Fatality: A Case Report with Postmortem Concentrations". Journal of Analytical Toxicology. 40 (9): 761–766. doi:10.1093/jat/bkw096. PMID 27650310.