Fentanyl 437-38-7
Fentanyl — brand names include Sublimaze, Actiq, Durogesic, Duragesic, Fentora, Onsolis and Instanyl . Historically it has been used to treat chronic breakthrough pain and is commonly used in pre-procedures. Fentanyl is approximately 100 times more potent than morphine, with 100 micrograms of Fentanyl approximately equivalent to 10 mg of morphine and 75 mg of pethidine (meperidine) in analgesic activity. It has an LD50 of 3. 1 milligrams per kilogram in rats, 0. 03 milligrams per kilogram in monkeys, and an undetermined LD50 in humans. Fentanyl was first synthesized by Dr. Paul Janssen in 1960 following the medical inception of pethidine several years earlier. Janssen developed fentanyl by assaying analogues of the structurally-related drug pethidine for opioid activity. The widespread use of fentanyl triggered the production of fentanyl citrate (fentanyl combined with citrate at a 1:1 ratio), which entered the clinical practice as a general anaesthetic under the trade name Sublimaze in the 1960s. Following this, many other fentanyl analogs were developed and introduced into the medical practice, including Sufentanil, Alfentanil, Remifentanil, and Lofentanil. In the mid 1990s, fentanyl saw its first widespread palliative use with the clinical introduction of the Duragesic patch, followed in the next decade by the introduction of the first quick-acting prescription formations of fentanyl for personal use, the Actiq lollipop and Fentora buccal tablets. Through the delivery method of transdermal patches, fentanyl is currently the most widely used synthetic opioid in clinical practice, with several new delivery methods currently in development.
History
Fentanyl was first synthesized by Paul Janssen under the label of his relatively newly formed Janssen Pharmaceutica in 1959. In the 1960s, fentanyl was introduced as an intravenous anesthetic under the trade name of Sublimaze. In the mid-1990s, Janssen Pharmaceutica developed and introduced into clinical trials the Duragesic patch, which is a formation of an inert alcohol gel infused with select fentanyl doses which are worn to provide constant administration of the opioid over a period of 48 to 72 hours. After a set of successful clinical trials, Duragesic fentanyl patches were introduced into the medical practice. Following the patch, a flavored lollipop of fentanyl citrate mixed with inert fillers was introduced under the brand name of Actiq, becoming the first quick-acting formation of fentanyl for use with chronic breakthrough pain. More recently, fentanyl has been developed into an effervescent tab for buccal absorption much like the Actiq lollipop, followed by a buccal spray device for fast-acting relief and other delivery methods currently in development. A new Fentanyl product has just been approved by the FDA for breakthrough cancer pain called Onsolis. It uses a new drug delivery technology called BEMA (fentanyl buccal soluble film) which is placed in the mouth on a small disc. There appears to be less abuse potential because the drug can not be crushed up and snorted like other fentanyl product. It also has a lower incidence of mouth ulcers for patients using fentanyl for breakthrough cancer pain.
| Systematic (IUPAC) name: | N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenyl-propanamide |
|---|---|
| Fentanyl CAS number: | 437-38-7 |
| ATC code: | N01AH01 N02AB03 |
| PubChem: | 3345 |
| DrugBank: | DB00813 |
| Formula: | C22H28N2O1 |
| Molecular mass: | 336.471 g/mol |
| Fentanyl Assay/Purity: | Typically NLT 98% |
