CHEBI:2569 - alfentanil

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ChEBI Name alfentanil
ChEBI ID CHEBI:2569
Definition A member of the class of piperidines that is piperidine having a 2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl group at the 1-position as well as N-phenylpropanamido- and methoxymethyl groups at the 4-position.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000000601281
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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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Formula C21H32N6O3
Net Charge 0
Average Mass 416.51720
Monoisotopic Mass 416.25359
InChI 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
InChIKey IDBPHNDTYPBSNI-UHFFFAOYSA-N
SMILES CCC(=O)N(c1ccccc1)C1(CCN(CCn2nnn(CC)c2=O)CC1)COC
Roles Classification
Biological Role(s): 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.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing alfentanil (CHEBI:2569) has role μ-opioid receptor agonist (CHEBI:55322)
alfentanil (CHEBI:2569) has role central nervous system depressant (CHEBI:35488)
alfentanil (CHEBI:2569) has role intravenous anaesthetic (CHEBI:38877)
alfentanil (CHEBI:2569) has role opioid analgesic (CHEBI:35482)
alfentanil (CHEBI:2569) has role peripheral nervous system drug (CHEBI:49110)
alfentanil (CHEBI:2569) is a monocarboxylic acid amide (CHEBI:29347)
alfentanil (CHEBI:2569) is a piperidines (CHEBI:26151)
IUPAC Name
N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide
INNs Sources
alfentanil KEGG DRUG
alfentanilum DrugBank
Synonyms Sources
Alfentanyl DrugBank
N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide ChemIDplus
Manual Xrefs Databases
114 DrugCentral
Alfentanil Wikipedia
C08005 KEGG COMPOUND
D07122 KEGG DRUG
DB00802 DrugBank
DE2819873 Patent
HMDB0014940 HMDB
US2014005223 Patent
US4167574 Patent
View more database links
Registry Numbers Types Sources
1188293 Reaxys Registry Number Reaxys
71195-58-9 CAS Registry Number KEGG DRUG
71195-58-9 CAS Registry Number ChemIDplus
Citations
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]
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]
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]
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]
Last Modified
22 February 2017