Fentanyl

Chemical Structure of Fentanyl

Fentanyl is a potent synthetic opioid analgesic which is active at very low doses. It has a rapid onset and short duration of action, and is used in the treatment of pain as well as in anesthesia.

Fentanyl is a fully synthetic opioid, and was first synthesized in 1960. Fentanyl is approximately 100 times more potent than morphine, and dosages are often given in micrograms (symbol: µg or mcg); where 1000 micrograms is equal to 1 milligram (mg). Fentanyl was first used in the 1960s as an anesthetic under the brand name Sublimaze. It was not until the mid-1990s that fentanyl was introduced for widespread use with the introduction of a transdermal patch under the brand name Duragesic. During the next decade, quick-acting prescription formulations of fentanyl were introduced, such as the Actiq lollipop and Fentora buccal tablets. Currently, fentanyl is the most widely used synthetic opiate medication.

The transdermal patches are the most common form of fentanyl sold on the street. Abusers will cut open a patch to access the fentanyl gel inside, then usually either smoke, or rub a small amount on their gums and inside of their cheek. Since the patches are designed to release small amounts of fentanyl over a period of 72 hours, cutting open a patch exposes all of the fentanyl at once. If a user is not careful, he or she could easily use too large of an amount and accidentally overdose. Newer patches that are manufactured are designed with a different system then the gel reservoir, making it harder to cut open and extract all the gel containing the fentanyl. Fentanyl has also been sold on the street as heroin or sold combined with heroin, leading to some overdose deaths as a result.

Brand Names

Actiq, Duragesic, Fentora, Lazanda, Onsolis

Street Names

Fent, percopop, China white

Formulations

• Actiq - lozenge, fentanyl citrate: 200 mcg, 400 mcg, 600 mcg, 800 mcg, 1200 mcg, 1600 mcg
• Duragesic - transdermal patch, fentanyl: 12 mcg/hr, 25 mcg/hr, 50 mcg/hr, 75 mcg/hr, 100 mcg/hr (for 72 hours)
• Fentora - buccal tablet, fentanyl citrate: 100 mcg, 200 mcg, 400 mcg, 600 mcg, 800 mcg
• Onsolis - buccal soluble film, fentanyl citrate: 200 mcg, 400 mcg, 600 mcg, 800 mcg, 1200 mcg
• Lazanda - nasal spray, fentanyl: 100 mcg/100 mcL, 400 mcg/100 mcL

Medical Uses

• relief of moderate to severe pain, chronic pain
• treatment of breakthrough cancer pain
• provide anesthesia and analgesia in operating rooms, ICU, oral surgery, etc.

Route of Administration

transdermal, intramuscular (IM), intravenous (IV), oral, sublingual, buccal, intranasal

Half-life

2.5 min (IV), 6.5 min (intranasal), 3-12 h (transdermal)

Medical Dosage

• pain relief: 25 mcg/h transdermal patch every 72 h; 100 mcg buccal tablet
• premedication for anesthesia: 50 to 100 mcg intramuscular (IM) 30-60 min prior to surgery; 5mcg/kg buccal lozenge
• general anesthesia: 2 to 25 mcg/kg intravenous (IV)

Legality

• Fentanyl is a Schedule II drug in the United States.
Fentanyl is a Schedule I drug in Canada.

Images

• Tablets/Film
• Patches
• Lozenges
• Intravenous

References

• Liappas IA, Dimopoulos NP, Mellos E, Gitsa OE, Liappas AI, Rabavilas AD. Oral transmucosal abuse of transdermal fentanyl. Journal of Psychopharmacology Jun 2004; 18(2):277-80. [PubMed]
• Kram TC, Cooper DA, Allen AC. Behind the identification of China White. Analytical Chemistry Oct 1981; 53(12):1379A-1386A. [Full Text]
• Schumacher MA, Basbaum AI, Way WL, Opioid Analgesics & Antagonists (Chapter 31) in: Basic and Clinical Pharmacology. 12e. Katzung BG, Masters SB, Trevor AJ (Editors). McGraw-Hill / Lange, 2012.
• Clinical Practice Guideline for Management of Opioid Therapy for Chronic Pain. United States Department of Veterans Affairs / Department of Defense, May 2010. [PDF]
• Controlled Substances - Alphabetical Order. DEA Office of Diversion Control, May 2013. [PDF]
• Controlled Drugs and Substances Act. Minister of Justice, Canada, Nov 2012. [PDF]

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