Fentanyl

Fentanyl
Clinical data
Pronunciation/ˈfɛntəˌnɪl/, often mispronounced /ˈfɛntəˌnɒl/
Trade namesActiq, Duragesic, Sublimaze, others
AHFS/Drugs.comMonograph
MedlinePlusa605043
License data
Pregnancy
category
  • AU: C
Dependence
liability		High[1]
Addiction
liability		Very high[2]
Routes of
administration		Buccal, epidural, intramuscular, intrathecal, intravenous, sublingual, transdermal
Drug classOpioid
ATC code
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class A1 (Narcotic drugs)
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • NZ: Class B
  • UK: Class A
  • US: Schedule II
  • UN: Narcotic Schedule I
  • EU: Rx-only[3][4]
Pharmacokinetic data
Bioavailability
Protein binding80–85%[13]
MetabolismLiver, primarily by CYP3A4
Onset of action5 minutes[14]
Elimination half-lifeIV: 6 mins (T1/2 α)
1 hours (T1/2 β)
16 hours (T1/2 ɣ)
Intranasal: 15–25 hours[15]
Transdermal: 20–27 hours[15]
Sublingual: 5–13.5 hours[15]
Buccal: 3.2–6.4 hours[15]
Duration of actionIV: 30–60 minutes[14][16]
ExcretionMostly urinary (metabolites, < 10% unchanged drug)[15]
Identifiers
IUPAC name
  • N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.006.468
Chemical and physical data
FormulaC22H28N2O
Molar mass336.479 g·mol−1
3D model (JSmol)
Density1.1 g/cm3
Melting point87.5 °C (189.5 °F)
SMILES
  • O=C(CC)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3
InChI
  • InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19/h3-12,21H,2,13-18H2,1H3 Y
  • Key:PJMPHNIQZUBGLI-UHFFFAOYSA-N Y
  (verify)

Fentanyl is a highly potent synthetic piperidine opioid primarily used as an analgesic (pain medication). It is 30 to 50 times more potent than heroin and 50 to 100 times more potent than morphine.[17] Its primary clinical utility is in pain management for cancer patients and those recovering from painful surgeries.[18][19] Fentanyl is also used as a sedative for intubated patients.[20] Depending on the method of delivery, fentanyl can be very fast acting and ingesting a relatively small quantity can cause overdose.[21] Fentanyl works by activating μ-opioid receptors.[15] Fentanyl is sold under the brand names Actiq, Duragesic, and Sublimaze, among others.[22]

Pharmaceutical fentanyl's adverse effects are similar to those of other opioids and narcotics[23] including addiction, confusion, respiratory depression (which, if extensive and untreated, may lead to respiratory arrest), drowsiness, nausea, visual disturbances, dyskinesia, hallucinations, delirium, a subset of the latter known as "narcotic delirium", narcotic ileus, muscle rigidity, constipation, loss of consciousness, hypotension, coma, and death.[20] Alcohol and other drugs (e.g., cocaine and heroin) can synergistically exacerbate fentanyl's side effects. Naloxone and naltrexone are opioid antagonists that reverse the effects of fentanyl.

Fentanyl was first synthesized by Paul Janssen in 1959 and was approved for medical use in the United States in 1968.[15][24] In 2015, 1,600 kilograms (3,500 pounds) were used in healthcare globally.[25] As of 2017, fentanyl was the most widely used synthetic opioid in medicine;[26] in 2019, it was the 278th most commonly prescribed medication in the United States, with more than a million prescriptions.[27][28] It is on the World Health Organization's List of Essential Medicines.[29]

Fentanyl is contributing to an epidemic of synthetic opioid drug overdose deaths in the United States. From 2011 to 2021, deaths from prescription opioid (natural and semi-synthetic opioids and methadone) per year remained stable, while synthetic opioid (primarily fentanyl) deaths per year increased from 2,600 overdoses to 70,601.[30] Since 2018, fentanyl and its analogues have been responsible for most drug overdose deaths in the United States, causing over 71,238 deaths in 2021.[31][30][32] Fentanyl constitutes the majority of all drug overdose deaths in the United States since it overtook heroin in 2018.[31] The United States National Forensic Laboratory estimates fentanyl reports by federal, state, and local forensic laboratories increased from 4,697 reports in 2014 to 117,045 reports in 2020.[33] Fentanyl is often mixed, cut, or ingested alongside other drugs, including cocaine and heroin.[33] Fentanyl has been reported in pill form, including pills mimicking pharmaceutical drugs such as oxycodone.[33] Mixing with other drugs or disguising as a pharmaceutical makes it difficult to determine the correct treatment in the case of an overdose, resulting in more deaths.[20] In an attempt to reduce the number of overdoses from taking other drugs mixed with fentanyl, drug testing kits, strips, and labs are available.[34][35] Fentanyl's ease of manufacture and high potency makes it easier to produce and smuggle, resulting in fentanyl replacing other abused narcotics and becoming more widely used.[36]

  1. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and administrative procedures. Elsevier Health Sciences. p. 571. ISBN 978-1-4557-0150-6. Archived from the original on 10 January 2023. Retrieved 20 August 2019.
  2. ^ Ciccarone D (August 2017). "Fentanyl in the US heroin supply: A rapidly changing risk environment". The International Journal on Drug Policy. 46: 107–111. doi:10.1016/j.drugpo.2017.06.010. PMC 5742018. PMID 28735776.
  3. ^ "Instanyl EPAR". European Medicines Agency (EMA). 20 July 2009. Retrieved 11 September 2024.
  4. ^ "Effentora EPAR". European Medicines Agency (EMA). 4 April 2008. Retrieved 12 October 2024.
  5. ^ a b Taylor KP, Singh K, Goyal A (6 July 2023). "Fentanyl Transdermal". StatPearls. Saint James School of Medicine & University of Kansas Medical Center: StatPearls Publishing. PMID 32310428. Retrieved 12 July 2025.
  6. ^ Varvel JR, Shafer SL, Hwang SS, Coen PA, Stanski DR (1 June 1989). "Absorption Characteristics of Transdermally Administered Fentanyl". Anesthesiology. 70 (6): 928–934. doi:10.1097/00000542-198906000-00008. PMID 2729633.
  7. ^ Nakhaee S, Saeedi F, Mehrpour O (December 2023). "Clinical and pharmacokinetics overview of intranasal administration of fentanyl". Heliyon. 9 (12) e23083. Bibcode:2023Heliy...923083N. doi:10.1016/j.heliyon.2023.e23083. ISSN 2405-8440. PMC 10746457. PMID 38144320.
  8. ^ a b Vasisht N, Gever LN, Tagarro I, Finn AL (July 2010). "Single-Dose Pharmacokinetics of Fentanyl Buccal Soluble Film". Pain Medicine. 11 (7): 1017–1023. doi:10.1111/j.1526-4637.2010.00875.x. PMC 2955962. PMID 20492573.
  9. ^ Beng Stephen Lim C, Schug SA, Bruce Sunderland V, James Paech M, Liu Y (September 2012). "A Phase I Pharmacokinetic and Bioavailability Study of a Sublingual Fentanyl Wafer in Healthy Volunteers". Anesthesia and Analgesia. 115 (3): 554–559. doi:10.1213/ANE.0b013e3182575cbf. PMID 22584544.
  10. ^ Taylor D (July 2013). "Single-dose fentanyl sublingual spray for breakthrough cancer pain". Clinical Pharmacology : Advances and Applications. 5: 131–141. doi:10.2147/CPAA.S26649. PMC 3726301. PMID 23901300.
  11. ^ Mather LE, Woodhouse A, Ward ME, Farr SJ, Rubsamen RA, Eltherington LG (July 1998). "Pulmonary administration of aerosolized fentanyl: pharmacokinetic analysis of systemic delivery". British Journal of Clinical Pharmacology. 46 (1): 37–43. doi:10.1046/j.1365-2125.1998.00035.x. PMC 1873979. PMID 9690947.
  12. ^ "Fentanyl Citrate Injection, USP" (PDF). FDA.gov. Food and Drug Administration. November 2012. Retrieved 12 July 2025.
  13. ^ Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R (March 2015). "Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and α-1 acid glycoprotein". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 45 (3): 207–212. doi:10.3109/00498254.2014.971093. PMID 25314012. S2CID 21109003.
  14. ^ a b Clinically Oriented Pharmacology (2nd ed.). Quick Review of Pharmacology. 2010. p. 172.
  15. ^ a b c d e f g "Fentanyl, Fentanyl Citrate, Fentanyl Hydrochloride". The American Society of Health-System Pharmacists. Archived from the original on 14 December 2017. Retrieved 8 December 2017.
  16. ^ "Guideline for administration of fentanyl for pain relief in labour" (PDF). RCP. Archived (PDF) from the original on 4 March 2016. Retrieved 7 October 2015. Onset of action after I.V. administration of Fentanyl is 3–5 minutes; duration of action is 30–60 minutes.
  17. ^ Han Y, Yan W, Zheng Y, Khan MZ, Yuan K, Lu L (14 November 2018). "Fentanyl". Nature. 9 (1): 282. doi:10.1038/s41398-019-0625-0. PMC 6848196. PMID 31712552.
  18. ^ "Fentanyl". U.S. Centers for Disease Control and Prevention (CDC). 7 October 2022. Archived from the original on 28 April 2022. Retrieved 20 February 2023.
  19. ^ "Fentanyl: MedlinePlus Drug Information". MedlinePlus. Archived from the original on 27 November 2023. Retrieved 5 November 2023.
  20. ^ a b c Ramos-Matos CF, Bistas KG, Lopez-Ojeda W (2022). "Fentanyl". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 29083586. Archived from the original on 15 March 2023. Retrieved 20 February 2023.
  21. ^ "Fentanyl". National Institute on Drug Abuse. 21 December 2021. Archived from the original on 20 February 2023. Retrieved 20 February 2023.
  22. ^ "Fentanyl DrugFacts". National Institute on Drug Abuse. 1 June 2021. Archived from the original on 11 May 2023. Retrieved 20 February 2023.
  23. ^ "Fentanyl: Uses, Warnings & Side Effects". Cleveland Clinic. Archived from the original on 5 November 2023. Retrieved 5 November 2023.
  24. ^ Stanley TH (April 1992). "The history and development of the fentanyl series". Journal of Pain and Symptom Management. 7 (3 Suppl): S3 – S7. doi:10.1016/0885-3924(92)90047-L. PMID 1517629.
  25. ^ Narcotic Drugs Estimated World Requirements for 2017 / Statistics for 2015 (PDF) (Report). New York: United Nations. 2016. p. 40. ISBN 978-92-1-048163-2. Archived (PDF) from the original on 22 October 2017. Retrieved 14 December 2017.
  26. ^ "Fentanyl and analogues". LiverTox. 16 October 2017. Archived from the original on 7 January 2017. Retrieved 14 December 2017.
  27. ^ "The Top 300 of 2019". ClinCalc. Archived from the original on 12 February 2021. Retrieved 7 October 2022.
  28. ^ "Fentanyl Drug Usage Statistics". ClinCalc. Archived from the original on 11 April 2020. Retrieved 7 October 2022.
  29. ^ Organization WH (2021). World Health Organization model list of essential medicines (22nd list (2021) ed.). Geneva, CH: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  30. ^ a b "Drug Overdose Death Rates". National Institute on Drug Abuse. 9 February 2023. Archived from the original on 23 February 2023. Retrieved 20 February 2023.
  31. ^ a b Reinberg S (12 December 2018). "Fentanyl overtakes heroin as the No. 1 opioid overdose killer". CBS News. CBS Interactive Inc. Archived from the original on 12 December 2018. Retrieved 20 February 2023.
  32. ^ "U.S. Overdose Deaths In 2021 Increased Half as Much as in 2020 – But Are Still Up 15%". U.S. Centers for Disease Control and Prevention (CDC). 11 May 2022. Archived from the original on 10 August 2022. Retrieved 5 May 2023.
  33. ^ a b c Cite error: The named reference www.dea.gov was invoked but never defined (see the help page).
  34. ^ "DrugsData.org: Lab Analysis / Drug Checking for Recreational Drugs". DrugsData. Retrieved 12 December 2023.
  35. ^ Nasir A. "Drug Checking". DanceSafe. Retrieved 12 December 2023.
  36. ^ Falco G (8 January 2023). "China's Role in Illicit Fentanyl Running Rampant on US Streets". Congressman David Trone. Archived from the original on 16 February 2023. Retrieved 20 February 2023.
This article is issued from Wikipedia. The text is available under Creative Commons Attribution-Share Alike 4.0 unless otherwise noted. Additional terms may apply for the media files.