Trefentanil

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Trefentanil
Trefentanil.png
Systematic (IUPAC) name
N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl}-N-(2-fluorophenyl)propanamide
Identifiers
CAS Number 120656-93-1 N
ATC code none
PubChem CID: 60728
ChemSpider 54732 YesY
UNII 36QM58LVGU YesY
ChEMBL CHEMBL84617 YesY
Chemical data
Formula C25H31FN6O2
Molecular mass 466.551 g/mol
  • Fc1ccccc1N(C(=O)CC)C4(c2ccccc2)CCN(CCN3\N=N/N(C3=O)CC)CC4
  • InChI=1S/C25H31FN6O2/c1-3-23(33)32(22-13-9-8-12-21(22)26)25(20-10-6-5-7-11-20)14-16-29(17-15-25)18-19-31-24(34)30(4-2)27-28-31/h5-13H,3-4,14-19H2,1-2H3 YesY
  • Key:RJSCINHYBGMIFT-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

Trefentanil (A-3665) is an opioid analgesic that is an analogue of fentanyl and was developed in 1992.[1]

Trefentanil is most similar to short-acting fentanyl analogues such as alfentanil. In comparative studies, trefentanil was slightly more potent and shorter acting than alfentanil as an analgesic,[2] but induced significantly more severe respiratory depression.[3] For this reason trefentanil has not been adopted for clinical use, although it is still used in research.

Trefentanil has very similar effects to alfentanil, much like those of fentanyl itself but more potent and shorter lasting. 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.[4] The risk of respiratory depression is especially high with potent fentanyl analogues such as alfentanil and trefentanil, and these drugs pose a significant risk of death if used outside of a hospital setting with appropriate artificial breathing apparatus available.

References

  1. ↑ Cambareri JJ, Afifi MS, Glass PS, Esposito BF, Camporesi EM. A-3665, a new short-acting opioid: a comparison with alfentanil. Anesthesia and Analgesia. 1993 Apr;76(4):812-6.
  2. ↑ Lemmens HJ, Dyck JB, Shafer SL, Stanski DR. Pharmacokinetic-pharmacodynamic modeling in drug development: application to the investigational opioid trefentanil. Clinical Pharmacology and Therapeutics. 1994 Sep;56(3):261-71.
  3. ↑ Cambareri JJ, Afifi MS, Glass PS, Esposito BF, Camporesi EM. A-3665, a new short-acting opioid: a comparison with alfentanil. Anesthesia and Analgesia. 1993 Apr;76(4):812-6.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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