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Alfentanil

From Wikipedia, the free encyclopedia
Synthetic opioid analgesic
Pharmaceutical compound
Alfentanil
Above: Alfentanil structureBelow: 3D model of alfentanil molecule
Clinical data
Trade namesAlfenta, Rapifen, others
Other namesR-39209
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa601130
Routes of
administration
Intravenous,subcutaneous
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityIV/IM/SC: 100%
Protein binding92%
MetabolismHepatic
Eliminationhalf-life90–111 minutes
Duration of action15 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
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.295.336Edit this at Wikidata
Chemical and physical data
FormulaC21H32N6O3
Molar mass416.526 g·mol−1
3D model (JSmol)
Melting point140.8 °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 checkY
  • Key:IDBPHNDTYPBSNI-UHFFFAOYSA-N checkY
  (verify)

Alfentanil, sold under the brand nameAlfenta among others, is a potent, short-acting syntheticopioidanalgesic drug used foranesthesia insurgery. It is an analogue offentanyl 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 anagonist of theμ-opioid receptor.

While alfentanil tends to cause fewercardiovascular complications than other similar drugs such as fentanyl andremifentanil, it tends to give strongerrespiratory 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, duringnerve blocks), alfentanil is administered by theparenteral (injected) route for fast-onset and precise control of dosage.

Discovered atJanssen Pharmaceutica in 1976, alfentanil is classified as aSchedule II drug in the United States.[4]

History

[edit]

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

References

[edit]
  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. Retrieved2023-08-16.
  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 fromthe original on 2007-02-02. Retrieved2007-01-23.
  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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