Alfentanil

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Alfentanil
Alfentanil-2D-skeletal.svg
Alfentanil 3D.png
Above: Alfentanil structure Below: 3D model of alfentanil molecule
Clinical data
Trade names Alfenta, Rapifen, others
Other namesR-39209
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601130
Routes of
administration 		Intravenous, subcutaneous
Drug class Opioid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability IV/IM/SC: 100%
Protein binding 92%
Metabolism Hepatic
Elimination half-life 90–111 minutes
Duration of action 15 minutes [2]
Identifiers
  • N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.295.336 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H32N6O3
Molar mass 416.526 g·mol−1
3D model (JSmol)
Melting point 140.8 °C (285.4 °F)
  • O=C1N(\N=N/N1CC)CCN3CCC(N(c2ccccc2)C(=O)CC)(CC3)COC
  • InChI=1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3 Yes check.svgY
  • Key:IDBPHNDTYPBSNI-UHFFFAOYSA-N Yes check.svgY
   (verify)

Alfentanil, sold under the brand name Alfenta among others, is a potent, short-acting synthetic opioid analgesic drug used for anesthesia in surgery. It is an analogue of fentanyl with around one-fourth to one-tenth the potency, one-third the duration of action, and an onset of action four times faster than that of fentanyl. [3] Alfentanil has a pKa of approximately 6.5, which leads to a very high proportion of the drug being uncharged at physiologic pH, a characteristic responsible for its rapid-onset. It is an agonist of the μ-opioid receptor.

Contents

While alfentanil tends to cause fewer cardiovascular complications than other similar drugs such as fentanyl and remifentanil, it tends to give stronger respiratory depression and so requires careful monitoring of breathing and vital signs. Almost exclusively used by anesthesia providers during portions of a case where quick, fast-acting (though not long-lasting) pain control is needed (as, for example, during nerve blocks), alfentanil is administered by the parenteral (injected) route for fast-onset and precise control of dosage.

Discovered at Janssen Pharmaceutica in 1976, alfentanil is classified as a Schedule II drug in the United States. [4]

History

The first application of the bolus, elimination, transfer infusion scheme used alfentanil and etomidate in 1983. [5]

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ↑ Shaw, Leslie M. (2001). The clinical toxicology laboratory : contemporary practice of poisoning evaluation. Washington, DC: AACC Press. p. 89. ISBN   9781890883539.
  3. ↑ Jacob Mathew, J. Kendall Killgore. Methods for the synthesis of alfentanil, sufentanil, and remifentanil. US Patent 7,208,604
  4. ↑ "From DEA website, accessed 23 Jan 2007". Archived from the original on 2007-02-02. Retrieved 2007-01-23.
  5. ↑ Lamont LA, Creighton CM (11 September 2024). "General Pharmacology of Anesthetic and Analgesic Drugs". In Lamont L, Grimm K, Robertson S, Love L, Schroeder C (eds.). Veterinary Anesthesia and Analgesia, The 6th Edition of Lumb and Jones. Wiley Blackwell. p. 303. ISBN   978-1-119-83027-6.
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