Source of information: Drugbank (External Link). Last updated on: 3rd July 18
*Trade Name used in the content below may not be the same as the HSA-registered product.
Active Ingredient / Synonyms
1-Phenethyl-4-(N-phenylpropionamido)piperidine | 1-phenethyl-4-N-propionylanilinopiperidine | Fentanil | Fentanila | Fentanilo | Fentanyl | Fentanyl CII | Fentanylum | N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide | N-(1-phenethyl-4-piperidyl)propionanilide | N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide | N-(1-phenethylpiperidin-4-yl)-N-phenylpropionamide | N-phenethyl-4-(N-propionylanilino)piperidine | N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide | Phentanyl | Fentanyl |
A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078)
For the treatment of cancer patients with severe pain that breaks through their regular narcotic therapy.
Mechanism of Action
Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Fentanyl's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hypopolarization and reduced neuronal excitability.
Fentanyl is an opioid analgesic. Fentanyl interacts predominately with the opioid mu-receptor but also binds to kappa and delta-type opioid receptors. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, Fentanyl exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Fentanyl may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Fentanyl depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
Bioavailability is 92% following transdermal administration and 50% following buccal administration.
* 3 to 8 L/kg [Surgical Patients] * 0.8 to 8 [Hepatically Impaired Patients]
Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system.
Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system and mostly eliminated in urine. Within 72 hours of IV fentanyl administration, approximately 75% of the dose is excreted in urine, mostly as metabolites with less than 10% representing unchanged drug.
7 hours (range 3-12)
* 27 – 75 L/h [Surgical Patients receving IV administration] * 3 – 80 L/h [Hepatically Impaired Patients receving IV administration] * 30 – 78 L/h [Renally Impaired Patients receving IV administration]
Fentanyl has an LD50 of 3.1 milligrams per kilogram in rats, and, 0.03 milligrams per kilogram in monkeys. The LD50 in humans is not known.
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