View source for Alfentanil

{{Short description|Synthetic opioid analgesic}}
{{Drugbox
| verifiedrevid = 477317188
| class = [[Opioid]]
| IUPAC_name = ''N''<nowiki>-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1</nowiki>''H''-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-''N''-phenylpropanamide
| image = Alfentanil-2D-skeletal.svg
| image_class = skin-invert-image
| width = 220px
| caption = Above: Alfentanil structure
Below: 3D model of alfentanil molecule
| image2 = Alfentanil 3D.png
| image_class2 = bg-transparent
| width2 = 220px

<!--Clinical data-->| tradename = Alfenta, Rapifen, others
| Drugs.com = {{drugs.com|CONS|alfentanil}}
| MedlinePlus = a601130
| legal_AU = S8
| legal_BR = A1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule I
| legal_UK = Class A
| legal_US = Schedule II
| legal_DE = Anlage III
| routes_of_administration = [[Intravenous therapy|Intravenous]], [[subcutaneous administration|subcutaneous]]

<!--Pharmacokinetic data-->| bioavailability = IV/IM/SC: 100%
| protein_bound = 92%
| metabolism = [[Liver|Hepatic]]
| onset = 
| elimination_half-life = 90–111 minutes
| duration_of_action = 15 minutes<ref>{{cite book|last1=Shaw|first1=Leslie M.|title=The clinical toxicology laboratory : contemporary practice of poisoning evaluation|date=2001|publisher=AACC Press|location=Washington, DC|isbn=9781890883539|page=89|url=https://books.google.com/books?id=pXvFGqz44pYC&pg=PA89}}</ref>

<!--Identifiers-->| IUPHAR_ligand = 7108
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 71195-58-9
| ATC_prefix = N01
| ATC_suffix = AH02
| PubChem = 51263
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00802
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 46451
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1N74HM2BS7
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07122
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2569
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| synonyms = R-39209
| ChEMBL = 634

<!--Chemical data-->| C = 21
| H = 32
| N = 6
| O = 3
| smiles = O=C1N(\N=N/N1CC)CCN3CCC(N(c2ccccc2)C(=O)CC)(CC3)COC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IDBPHNDTYPBSNI-UHFFFAOYSA-N
| melting_point = 140.8
}}
'''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.<ref>[https://patents.google.com/patent/US7208604 Jacob Mathew, J. Kendall Killgore. Methods for the synthesis of alfentanil, sufentanil, and remifentanil. US Patent 7,208,604]</ref> 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]].

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 block]]s), alfentanil is administered by the [[wikt:parenteral|parenteral]] (injected) route for fast-onset and precise control of dosage.

Discovered at [[Janssen Pharmaceutica]] in 1976, alfentanil is classified as a [[Controlled Substances Act#Schedule II drugs|Schedule II]] drug in the United States.<ref name="http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched2.htm">{{Cite web |url=http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched2.htm |title=From DEA website, accessed 23 Jan 2007 |access-date=2007-01-23 |archive-url=https://web.archive.org/web/20070202220921/http://www.deadiversion.usdoj.gov/schedules/listby_sched/sched2.htm |archive-date=2007-02-02 |url-status=dead }}</ref>
==History==
The first application of the bolus, elimination, transfer infusion scheme used alfentanil and [[etomidate]] in 1983.<ref>{{cite book | vauthors = Lamont LA, Creighton CM | chapter = General Pharmacology of Anesthetic and Analgesic Drugs | title = Veterinary Anesthesia and Analgesia, The 6th Edition of Lumb and Jones | page = 303 | isbn = 978-1-119-83027-6 | veditors = Lamont L, Grimm K, Robertson S, Love L, Schroeder C | date = 11 September 2024 | publisher = Wiley Blackwell }}</ref>

==References==
{{Reflist}}

==External links==
* [https://web.archive.org/web/20020805220012/http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a601130.html Medline Plus Patient Information - 09/01/2010]
* [https://www.fda.gov/drugs/drug-interactions-labeling/drug-development-and-drug-interactions-table-substrates-inhibitors-and-inducers fda.gov] February 2017
* Genf interaction table- https://www.hug.ch/sites/interhug/files/structures/pharmacologie_et_toxicologie_cliniques/carte_cytochromes_2016_final.pdf February 2017
{{Analgesics}}
{{General anesthetics}}
{{Opioidergics}}

[[Category:General anesthetics]]
[[Category:Synthetic opioids]]
[[Category:Piperidines]]
[[Category:Tetrazoles]]
[[Category:Ureas]]
[[Category:Ethers]]
[[Category:Lactams]]
[[Category:Anilides]]
[[Category:Mu-opioid receptor agonists]]
[[Category:Janssen Pharmaceutica]]
[[Category:Belgian inventions]]
[[Category:Fentanyl]]