Structure via PubChem · Public domain (PubChem)
alfentanil
Sign in to saveAlso known as Alfenta®, R-39209, Rapifen®, N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide, Alfentanyl, Alfentanilum
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. 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.
Chemical data
- Formula
- C21H32N6O3
- Molecular weight
- 416.5 g/mol
- IUPAC name
- N-[1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl]-N-phenylpropanamide
- SMILES
- CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCN3C(=O)N(N=N3)CC)COC
- InChIKey
- IDBPHNDTYPBSNI-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 81.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
2,610 papers- Alfentanil in anesthesia and analgesia.Drug intelligence & clinical pharmacy · 1986
- Alfentanil hydrochloride: a new short-acting narcotic analgesic for surgical procedures.Clinical pharmacy · 1987
- Population Pharmacokinetics of Alfentanil in Children.Journal of clinical pharmacology · 2025
- Alfentanil infusions in patients requiring intensive care.Clinical pharmacokinetics · 1988
- Alfentanil-based TIVA during remifentanil shortages: a need for guidance.Anaesthesia · 2023
via PubMed
~3 min read
Encyclopedic overview
3 sectionsContents
- History
- References
- External links
{{Drugbox | verifiedrevid = 477317188 | class = Opioid | IUPAC_name = 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 | 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
| tradename = Alfenta, Rapifen, others | Drugs.com = | MedlinePlus = a601130 | legal_AU = S8 | legal_BR = A1 | legal_BR_comment = | legal_CA = Schedule I | legal_UK = Class A | legal_US = Schedule II | legal_DE = Anlage III | routes_of_administration = Intravenous, subcutaneous
Excerpted from Wikipedia’s “alfentanil” article, available under the CC BY-SA 4.0 licence.