Alfentanil (R-39209), sold under the brand name Alfenta among others, is a potent but 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.
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.
Side effects of fentanyl analogs are similar to those of fentanyl itself and include itching, nausea and potentially life-threatening respiratory depression. 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.
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opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
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opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
intravenous anaesthetic
central nervous system depressant
A loosely defined group of drugs that tend to reduce the activity of the central nervous system.
peripheral nervous system drug
A drug that acts principally at one or more sites within the peripheral neuroeffector systems, the autonomic system, and motor nerve-skeletal system.
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View more via ChEBI Ontology
N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide
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alfentanil
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KEGG DRUG
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alfentanilum
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DrugBank
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Alfentanyl
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DrugBank
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N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide
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ChemIDplus
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1188293
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Reaxys Registry Number
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Reaxys
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71195-58-9
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CAS Registry Number
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KEGG DRUG
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71195-58-9
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CAS Registry Number
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ChemIDplus
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Tompkins DA, Smith MT, Bigelow GE, Moaddel R, Venkata SL, Strain EC (2014) The effect of repeated intramuscular alfentanil injections on experimental pain and abuse liability indices in healthy males. The Clinical journal of pain 30, 36-45 [PubMed:23446076] [show Abstract]
ObjectiveOpioid-induced hyperalgesia (OIH), increased sensitivity to noxious stimuli after repeated opioid exposures, has been demonstrated in preclinical studies. However, there is no accepted, prospective model of OIH after repeated opioid exposures currently available in humans. This study assessed a potential prospective OIH model.MethodsDouble-blind intramuscular injections of a short-acting opioid (alfentanil 15 mcg/kg; N=8) were compared to active placebo (diphenhydramine 25 mg; N=3) on cold and pressure pain testing and standard abuse liability measures in eight 10-hour sessions (1 injection/session) over 4 to 5 weeks in healthy, pain-free males. Decreases from session baseline pain threshold (PThr) and tolerance (PTol) were calculated to represent hyperalgesia, and were assessed both within and across sessions.ResultsMean decreases in cold PTol were seen in the alfentanil group at 180 minutes (-3.8 s, ±26.5) and 480 minutes (-1.63 s, ±31.5) after drug administration. There was a trend for differences between conditions on cold PThr hyperalgesia but not for pressure PThr. Alfentanil participants had greater mean ratings on Liking and High visual analog scales at peak effects (30 min), but these scores did not change across sessions.DiscussionRepeated alfentanil exposures over 4 to 5 weeks resulted in within session decreases in cold pain tolerance from baseline but these differences were not substantially different from diphenhydramine controls. The results did not support the phenomenon of OIH in this model, although definitive conclusions regarding the existence of OIH in humans likely requires a larger sample size or an alternative model. | Mao CL, Zientek KD, Colahan PT, Kuo MY, Liu CH, Lee KM, Chou CC (2006) Development of an enzyme-linked immunosorbent assay for fentanyl and applications of fentanyl antibody-coated nanoparticles for sample preparation. Journal of pharmaceutical and biomedical analysis 41, 1332-1341 [PubMed:16621415] [show Abstract] A sensitive enzyme-linked immunosorbent assay (ELISA) was developed for the detection of fentanyl in serum and urine. The ELISA used an indirect competitive method produced by coating the plate with thyroglobulin conjugated with fentanyl hapten. Antibodies against fentanyl-hemocyanin were detected by a goat-anti-rabbit antibody conjugated with alkaline phosphatase. Calibration standard curves ranged from 0.5ng/ml to 50mug/ml (IC(50)=10ng/ml), and the limits of detection were 0.5 and 1.0ng/ml for serum and urine, respectively. The intra- and inter-assay variations were less than 8% and 10%, respectively. The antibody produced against fentanyl completely cross-reacted with p-fluorofentanyl, thienylfentanyl and 3-methylthienylfentanyl, cross-reacted highly with carfentanil (85%), but was considered non-cross-reactive with alpha-methylfentanyl (5%), sufentanil (<1%), alfentanil (<1%) and lofentanil (<1%). Nano-sized iron oxide magnetic particles coated with the developed fentanyl antibody were capable of specific binding and releasing of fentanyl from urine samples. This enabled the drug to be effectively pre-concentrated and decreased the limit of detection by approximately one order of magnitude. The analytical background noise was significantly reduced to enable fentanyl detection at concentrations originally below chromatographic limit of detection. The change of platform for antibody binding with nanoparticles demonstrated a novel use of antibodies for sample preparation and should facilitate drug screening by traditional ELISA. | Salihoglu Z, Demiroluk S, Demirkiran, Kose Y (2002) Comparison of effects of remifentanil, alfentanil and fentanyl on cardiovascular responses to tracheal intubation in morbidly obese patients. European journal of anaesthesiology 19, 125-128 [PubMed:11999595] [show Abstract]
Background and objectiveThe effects of remifentanil, alfentanil and fentanyl were compared on cardiovascular responses to laryngoscopy and endotracheal intubation in morbidly obese patients.MethodsEighty morbidly obese ASA I-II patients were included in the study. Patients were randomly divided into four groups to receive either 1 microgkg(-1) fentanyl (Group F), 10 microgkg(-1) alfentanil (A), 1 microgkg(-1) followed by an infusion of 0.5 pg kg min(-1) remifentanil (R) or saline (P). The patients corrected weight was used to calculate the drug doses. Body mass indices (range) were: 54.3 +/- 7.37 (49-78.4), 55.67 +/- 7.44 (48.5-78.4), 53.17 +/- 5.36 (48.1-63.2), and 56.3 +/- 6.09 (46.6-67.7) kg m(-2), in Groups F, R, A and P respectively. Systolic, diastolic and mean arterial pressures and heart rate were measured non-invasively at three time points, which were 2 min before induction, 2 min after induction and 2 min after endotracheal intubation.ResultsAfter induction of anaesthesia, arterial pressures decreased significantly in all groups, but the decrease was more pronounced in Groups A and R. After induction, heart rate decreased significantly in all groups except in Group P. After intubation, haemodynamic responses were similar in the remifentanil, fentanyl and alfentanil groups and were within normal limits. In Group P, arterial pressures and heart rates were significantly higher.ConclusionsAlfentanil, fentanyl and remifentanil in the doses described had similar effects in controlling the haemodynamic response to tracheal intubation in ASA I-II morbidly obese patients. | Ross J, Kearse LA, Barlow MK, Houghton KJ, Cosgrove GR (2001) Alfentanil-induced epileptiform activity: a simultaneous surface and depth electroencephalographic study in complex partial epilepsy. Epilepsia 42, 220-225 [PubMed:11240593] [show Abstract]
PurposeAlfentanil is a high potency mu opiate receptor agonist commonly used during presurgical induction of anesthesia. This and other opiate receptor agonists have demonstrated proconvulsant effects in animals, but these properties have been less consistently demonstrated in humans. Most human scalp EEG studies have failed to demonstrate induction of epileptiform activity with these agents, which is inconsistent with findings using intracranial EEG. Simultaneous scalp and depth EEG recordings have yet to be performed in this setting. The relationship between opiate dose and proconvulsant activity is unclear.MethodsSimultaneous scalp and depth electrode recordings were performed on five patients with complex partial epilepsy (CPE) who underwent alfentanil anesthesia induction before depth electrode removal. Consecutive equal bolus doses of alfentanil were administered to each patient according to strict time intervals so as to assess their correlation with any induced epileptiform activity.ResultsEpileptiform activity was induced by alfentanil in three of five patients. Two of these patients had electrographic seizures. Epileptiform activity was only detected from the depth electrodes, occurring within 2 min of the first bolus dose in all three cases. Further increase or spread of epileptiform activity did not occur despite cumulative bolus doses of alfentanil.ConclusionsAlfentanil is proconvulsant in patients with CPE. Induced seizures may be subclinical and lack a scalp EEG correlate. There is a complex dose-response relationship. Alfentanil induction of anesthesia should be approached with caution in patients with CPE. |
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