Alfentanil
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| Systematic (IUPAC) name | |
|---|---|
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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
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| Clinical data | |
| Trade names | Alfenta |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| MedlinePlus | a601130 |
| Routes of administration |
Intravenous |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | 100% |
| Protein binding | 92% |
| Metabolism | Hepatic |
| Biological half-life | 90–111 minutes |
| Duration of action | 15 min[1] |
| Identifiers | |
| CAS Number | 71195-58-9  |
| ATC code | N01AH02 (WHO) |
| PubChem | CID 51263 |
| IUPHAR/BPS | 7108 |
| DrugBank | DB00802 |
| ChemSpider | 46451 |
| UNII | 1N74HM2BS7 |
| KEGG | D07122 |
| ChEBI | CHEBI:2569 |
| ChEMBL | CHEMBL634 |
| Chemical data | |
| Formula | C21H32N6O3 |
| Molar mass | 416.517 g/mol |
| 3D model (Jmol) | Interactive image |
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| Physical data | |
| Melting point | 140.8 °C (285.4 °F) |
| (verify) | |
Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an analogue of fentanyl with around 1/4 to 1/10 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl.[2] Alfentanil has a pKa of approximately 6.5, which leads to a very high proportion of the drug being uncharged at physiologic pH. This unique characteristic is responsible for its rapid onset. It is an agonist at mu opioid receptors.
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 (i.e. during a nerve block, head pinning etc..) Alfentanil is administered by the parenteral (injected) route for fast onset of effects and precise control of dosage.
Alfentanil is a restricted drug which is classified as Schedule II in the USA, according to the U.S. DEA website.[3]
Alfentanil was discovered at Janssen Pharmaceutica in 1976.
Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening. 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.[4]
References[edit]
- ^ Shaw, Leslie M. (2001). The clinical toxicology laboratory : contemporary practice of poisoning evaluation. Washington, DC: AACC Press. p. 89. ISBN 9781890883539.
- ^ Jacob Mathew, J. Kendall Killgore. Methods for the synthesis of alfentanil, sufentanil, and remifentanil. US Patent 7,208,604
- ^ From DEA website, accessed 23 Jan 2007
- ^ Mounteney J, Giraudon I, Denissov G, Griffiths P (July 2015). "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe.". The international journal of drug policy. 26 (7): 626–631. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
