Brifentanil

Brifentanil
Clinical data
Other names	Brifentanil
ATC code	none;
Identifiers
	IUPAC name N-[(3R,4S)-1-[2-(4-Ethyl-5-oxotetrazol-1-yl)ethyl] -3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide;
CAS Number	101345-71-5;
PubChem CID	60672;
ChemSpider	54682 ;
UNII	6GDT77PQBW;
ChEMBL	ChEMBL2220476;
CompTox Dashboard (EPA)	DTXSID20143867 ;
Chemical and physical data
Formula	C20H29FN6O3
Molar mass	420.489 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc1ccccc1N(C(=O)COC)[C@H]3CCN(CCN2\N=N/N(C2=O)CC)C[C@H]3C;
	InChI InChI=1S/C20H29FN6O3/c1-4-25-20(29)26(23-22-25)12-11-24-10-9-17(15(2)13-24)27(19(28)14-30-3)18-8-6-5-7-16(18)21/h5-8,15,17H,4,9-14H2,1-3H3/t15-,17+/m1/s1 ; Key:KKMGCTVJCQYQPV-WBVHZDCISA-N ;
	(verify)

Brifentanil (A-3331) is an opioid analgesic that is an analogue of fentanyl and was developed in the early 1990s.^[1]

Brifentanil is most similar to highly potent, short-acting fentanyl analogues such as alfentanil. The effects of brifentanil are very similar to those of alfentanil, with strong but short lasting analgesia and sedation, and particularly notable itching and respiratory depression.^[2]

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.^[3] The risk of respiratory depression is especially high with potent fentanyl analogues such as alfentanil and brifentanil, and these drugs pose a significant risk of death if used outside of a hospital setting without an appropriate artificial breathing apparatus available.

References

^ Lalinde, N.; Moliterni, J.; Wright, D.; Spencer, H. K.; Ossipov, M. H.; Spaulding, T. C.; Rudo, F. G. (1990). "Synthesis and pharmacological evaluation of a series of new 1,4-disubstituted 3-methyl-piperidine analgesics". Journal of Medicinal Chemistry. 33 (10): 2876–82. doi:10.1021/jm00172a032. PMID 2170652.
^ Camporesi EM, Esposito B, Cigada M. Ventilatory response to hypoxia and hypercapnia after intravenous brifentanyl (a new synthetic narcotic). Minerva Anestesiologica. 1991 Sep;57(9):618, (Italian).
^ Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.

[Lalinde-1] Lalinde, N.; Moliterni, J.; Wright, D.; Spencer, H. K.; Ossipov, M. H.; Spaulding, T. C.; Rudo, F. G. (1990). "Synthesis and pharmacological evaluation of a series of new 1,4-disubstituted 3-methyl-piperidine analgesics". Journal of Medicinal Chemistry. 33 (10): 2876–82. doi:10.1021/jm00172a032. PMID 2170652.

[2] Camporesi EM, Esposito B, Cigada M. Ventilatory response to hypoxia and hypercapnia after intravenous brifentanyl (a new synthetic narcotic). Minerva Anestesiologica. 1991 Sep;57(9):618, (Italian).

[3] Jane Mounteney; Isabelle Giraudon; Gleb Denissov; Paul Griffiths (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal of Drug Policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.

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