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Identification
NameFentanyl
Accession NumberDB00813  (APRD00347, DB05853)
TypeSmall Molecule
GroupsApproved, Illicit, Investigational
Description

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)

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Phenethyl-4-(N-phenylpropionamido)piperidineNot AvailableNot Available
1-Phenethyl-4-N-propionylanilinopiperidineNot AvailableNot Available
Fentanil Not AvailableDCIT
FentanilaNot AvailableNot Available
FentaniloSpanishINN
FentanylGerman INN
FentanylFrench INN
FentanylumLatinINN
N-(1-Phenethyl-4-piperidinyl)-N-phenylpropionamideNot AvailableNot Available
N-(1-Phenethyl-4-piperidyl)propionanilideNot AvailableNot Available
N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamideNot AvailableNot Available
N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamideNot AvailableNot Available
N-Phenethyl-4-(N-propionylanilino)piperidineNot AvailableNot Available
N-Phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamideNot AvailableNot Available
PhentanylNot AvailableIS
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousHospira, Inc.1985-01-12Not AvailableUs
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousHospira, Inc.1985-01-12Not AvailableUs
Fentanylpatch12.5 ug/htransdermalSandoz,Inc.2004-10-01Not AvailableUs
Fentanylpatch25 ug/htransdermalSandoz,Inc.2004-10-01Not AvailableUs
Fentanylpatch50 ug/htransdermalSandoz,Inc.2004-10-01Not AvailableUs
Fentanylpatch75 ug/htransdermalSandoz,Inc.2004-10-01Not AvailableUs
Fentanylpatch100 ug/htransdermalSandoz,Inc.2004-10-01Not AvailableUs
Lazandaspray100 ugnasalDepomed, Inc.2011-10-17Not AvailableUs
Lazandaspray400 ugnasalDepomed, Inc.2011-10-17Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousAkorn, Inc.2012-03-22Not AvailableUs
Subsysspray.1 mgsublingualInsys Therapeutics, Inc.2012-03-13Not AvailableUs
Subsysspray.2 mgsublingualInsys Therapeutics, Inc.2012-03-13Not AvailableUs
Subsysspray.4 mgsublingualInsys Therapeutics, Inc.2012-03-13Not AvailableUs
Subsysspray.6 mgsublingualInsys Therapeutics, Inc.2012-03-13Not AvailableUs
Subsysspray.8 mgsublingualInsys Therapeutics, Inc.2012-03-13Not AvailableUs
Subsysspray.6 mgsublingualInsys Therapeutics, Inc.2012-08-30Not AvailableUs
Subsysspray.8 mgsublingualInsys Therapeutics, Inc.2012-08-30Not AvailableUs
Abstraltablet100 ugsublingualPro Strakan, Inc.2011-01-07Not AvailableUs
Abstraltablet200 ugsublingualPro Strakan, Inc.2011-01-07Not AvailableUs
Abstraltablet300 ugsublingualPro Strakan, Inc.2011-01-07Not AvailableUs
Abstraltablet400 ugsublingualPro Strakan, Inc.2011-01-07Not AvailableUs
Abstraltablet600 ugsublingualPro Strakan, Inc.2011-01-07Not AvailableUs
Abstraltablet800 ugsublingualPro Strakan, Inc.2011-01-07Not AvailableUs
Duragesicpatch12.5 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-07Not AvailableUs
Duragesicpatch25 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-07Not AvailableUs
Duragesicpatch50 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-07Not AvailableUs
Duragesicpatch75 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-07Not AvailableUs
Duragesicpatch100 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-07Not AvailableUs
Lazandaspray100 ugnasalArchimedes Pharma US Inc.2011-10-17Not AvailableUs
Lazandaspray400 ugnasalArchimedes Pharma US Inc.2011-10-17Not AvailableUs
Fentanyl Citratelozenge400 ugoral; transmucosalPhysicians Total Care, Inc.2008-12-19Not AvailableUs
Fentanyl Citratelozenge200 ugoral; transmucosalPhysicians Total Care, Inc.2009-04-24Not AvailableUs
Fentanyl Citratelozenge600 ugoral; transmucosalPhysicians Total Care, Inc.2009-04-24Not AvailableUs
Fentanyl Citratelozenge800 ugoral; transmucosalPhysicians Total Care, Inc.2009-04-24Not AvailableUs
Fentanyl Citratelozenge1200 ugoral; transmucosalPhysicians Total Care, Inc.2009-06-05Not AvailableUs
Fentanyl Citratelozenge200 ugtransmucosalCIMA Laboratories, Inc.2006-09-06Not AvailableUs
Fentanyl Citratelozenge400 ugtransmucosalCIMA Laboratories, Inc.2006-09-06Not AvailableUs
Fentanyl Citratelozenge600 ugtransmucosalCIMA Laboratories, Inc.2006-09-06Not AvailableUs
Fentanyl Citratelozenge800 ugtransmucosalCIMA Laboratories, Inc.2006-09-06Not AvailableUs
Fentanyl Citratelozenge1200 ugtransmucosalCIMA Laboratories, Inc.2006-09-06Not AvailableUs
Fentanyl Citratelozenge1600 ugtransmucosalCIMA Laboratories, Inc.2006-09-06Not AvailableUs
Abstraltablet100 ugsublingualGalena Biopharma, Inc.2013-08-08Not AvailableUs
Abstraltablet200 ugsublingualGalena Biopharma, Inc.2013-08-08Not AvailableUs
Abstraltablet300 ugsublingualGalena Biopharma, Inc.2013-08-08Not AvailableUs
Abstraltablet400 ugsublingualGalena Biopharma, Inc.2013-08-08Not AvailableUs
Abstraltablet600 ugsublingualGalena Biopharma, Inc.2013-08-08Not AvailableUs
Abstraltablet800 ugsublingualGalena Biopharma, Inc.2013-08-08Not AvailableUs
Actiqlozenge200 ugoral; transmucosalCephalon, Inc.1998-11-04Not AvailableUs
Actiqlozenge400 ugoral; transmucosalCephalon, Inc.1998-11-04Not AvailableUs
Actiqlozenge600 ugoral; transmucosalCephalon, Inc.1998-11-04Not AvailableUs
Actiqlozenge800 ugoral; transmucosalCephalon, Inc.1998-11-04Not AvailableUs
Actiqlozenge1200 ugoral; transmucosalCephalon, Inc.1998-11-04Not AvailableUs
Actiqlozenge1600 ugoral; transmucosalCephalon, Inc.1998-11-04Not AvailableUs
Fentanylpatch12.5 ug/htransdermalbryant ranch prepack2004-10-01Not AvailableUs
Fentanylpatch12 ugtransdermalDispensing Solutions, Inc.2004-10-01Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fentanylpatch, extended release25 ug/htransdermalTeva Pharmaceuticals USA Inc2008-12-22Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalTeva Pharmaceuticals USA Inc2008-12-22Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalTeva Pharmaceuticals USA Inc2008-10-20Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalTeva Pharmaceuticals USA Inc2008-10-20Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch, extended release50 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch, extended release75 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch, extended release100 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch12 ug/htransdermalMylan Pharmaceuticals Inc.2007-01-24Not AvailableUs
Fentanylpatch25 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-28Not AvailableUs
Fentanylpatch50 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-28Not AvailableUs
Fentanylpatch75 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-28Not AvailableUs
Fentanylpatch100 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-28Not AvailableUs
Fentanyl Citratelozenge200 ugtransmucosalMallinckrodt Inc.2010-01-15Not AvailableUs
Fentanyl Citratelozenge400 ugtransmucosalMallinckrodt Inc.2010-01-15Not AvailableUs
Fentanyl Citratelozenge600 ugtransmucosalMallinckrodt Inc.2010-01-15Not AvailableUs
Fentanyl Citratelozenge800 ugtransmucosalMallinckrodt Inc.2010-01-15Not AvailableUs
Fentanyl Citratelozenge1200 ugtransmucosalMallinckrodt Inc.2010-01-15Not AvailableUs
Fentanyl Citratelozenge1600 ugtransmucosalMallinckrodt Inc.2010-01-15Not AvailableUs
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousHospira, Inc.1991-09-24Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalActavis Pharma, Inc.2007-09-01Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalActavis Pharma, Inc.2007-09-01Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalActavis Pharma, Inc.2007-09-01Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalActavis Pharma, Inc.2007-09-01Not AvailableUs
Fentanyl - Novapluspatch, extended release25 ug/htransdermalWatson Laboratories, Inc.2007-09-01Not AvailableUs
Fentanyl - Novapluspatch, extended release50 ug/htransdermalWatson Laboratories, Inc.2007-09-01Not AvailableUs
Fentanyl - Novapluspatch, extended release75 ug/htransdermalWatson Laboratories, Inc.2007-09-01Not AvailableUs
Fentanyl - Novapluspatch, extended release100 ug/htransdermalWatson Laboratories, Inc.2007-09-01Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection50 ug/mLintravenousWest Ward Pharmaceutical Corp.1984-07-11Not AvailableUs
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-25Not AvailableUs
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-25Not AvailableUs
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-25Not AvailableUs
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-25Not AvailableUs
Fentanylpatch12 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2013-01-09Not AvailableUs
Fentanylpatch100 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2013-01-09Not AvailableUs
Fentanyl Citratelozenge800 ugoral; transmucosalLake Erie Medical DBA Quality Care Products LLC2011-10-17Not AvailableUs
Fentanylpatch, extended release2.5 mg/72htransdermalSTAT Rx USA LLC2007-08-20Not AvailableUs
Fentanylpatch, extended release5 mg/72htransdermalSTAT Rx USA LLC2007-08-20Not AvailableUs
Fentanyl Citratelozenge200 ugoral; transmucosalPar Pharmaceutical Inc.2011-10-17Not AvailableUs
Fentanyl Citratelozenge400 ugoral; transmucosalPar Pharmaceutical Inc.2011-10-17Not AvailableUs
Fentanyl Citratelozenge600 ugoral; transmucosalPar Pharmaceutical Inc.2011-10-17Not AvailableUs
Fentanyl Citratelozenge800 ugoral; transmucosalPar Pharmaceutical Inc.2011-10-17Not AvailableUs
Fentanyl Citratelozenge1200 ugoral; transmucosalPar Pharmaceutical Inc.2011-10-17Not AvailableUs
Fentanyl Citratelozenge1600 ugoral; transmucosalPar Pharmaceutical Inc.2011-10-17Not AvailableUs
Fentanylpatch25 ug/htransdermalPar Pharmaceutical Inc.2007-08-20Not AvailableUs
Fentanylpatch50 ug/htransdermalPar Pharmaceutical Inc.2007-08-20Not AvailableUs
Fentanylpatch75 ug/htransdermalPar Pharmaceutical Inc.2007-08-20Not AvailableUs
Fentanylpatch100 ug/htransdermalPar Pharmaceutical Inc.2007-08-20Not AvailableUs
Fentanylpatch, extended release2.5 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-09Not AvailableUs
Fentanylpatch, extended release5 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-09Not AvailableUs
Fentanylpatch, extended release7.5 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-09Not AvailableUs
Fentanylpatch, extended release10 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-09Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalH.J. Harkins Company, Inc.2010-03-01Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalH.J. Harkins Company, Inc.2010-03-01Not AvailableUs
Fentanylpatch2.55 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-14Not AvailableUs
Fentanylpatch5.1 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-14Not AvailableUs
Fentanylpatch7.65 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-14Not AvailableUs
Fentanylpatch10.2 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-14Not AvailableUs
Fentanylpatch1.28 mg/[USP'U]transdermalPhysicians Total Care, Inc.2008-11-18Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalApotex Corp.2010-03-01Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalApotex Corp.2010-03-01Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalApotex Corp.2010-03-01Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalApotex Corp.2010-03-01Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalApotex Corp.2013-04-04Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalApotex Corp.2013-04-04Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalApotex Corp.2013-04-04Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalApotex Corp.2013-04-04Not AvailableUs
Fentanylpatch25 ug/htransdermalSt. Marys Medical Park Pharmacy2011-01-26Not AvailableUs
Fentanylpatch50 ug/htransdermalSt. Marys Medical Park Pharmacy2011-01-26Not AvailableUs
Fentanylpatch100 ug/htransdermalSt. Marys Medical Park Pharmacy2011-01-26Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalbryant ranch prepack2010-03-01Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalbryant ranch prepack2010-03-01Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalbryant ranch prepack2010-03-01Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalbryant ranch prepack2010-03-01Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalbryant ranch prepack2013-04-04Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalbryant ranch prepack2013-04-04Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalbryant ranch prepack2013-04-04Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalbryant ranch prepack2007-09-01Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalbryant ranch prepack2007-09-01Not AvailableUs
Fentanylpatch, extended release50 ug/htransdermalbryant ranch prepack2007-09-01Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalbryant ranch prepack2007-09-01Not AvailableUs
Fentanylpatch25 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-01Not AvailableUs
Fentanylpatch50 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-01Not AvailableUs
Fentanylpatch75 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-01Not AvailableUs
Fentanylpatch100 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-01Not AvailableUs
Fentanylpatch, extended release25 ug/htransdermalDispensing Solutions Inc.2006-11-06Not AvailableUs
Fentanylpatch, extended release75 ug/htransdermalDispensing Solutions Inc.2006-11-06Not AvailableUs
Fentanylpatch, extended release100 ug/htransdermalDispensing Solutions Inc.2006-11-06Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
DurogesicJanssen
FentanestPfizer
NasalfentArchimedes
RapinylGedeon Richter
Brand mixtures
Brand NameIngredients
Innovar Injectiondroperidol + fentanyl citrate
Salts
Name/CASStructureProperties
Fentanyl citrate
990-73-8
Thumb
  • InChI Key: IVLVTNPOHDFFCJ-UHFFFAOYSA-N
  • Monoisotopic Mass: 528.247166138
  • Average Mass: 528.594
DBSALT000301
Categories
CAS number437-38-7
WeightAverage: 336.4705
Monoisotopic: 336.220163528
Chemical FormulaC22H28N2O
InChI KeyPJMPHNIQZUBGLI-UHFFFAOYSA-N
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
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide
SMILES
CCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPiperidines
Sub ClassFentanyls
Direct ParentFentanyls
Alternative Parents
Substituents
  • Fentanyl
  • Anilide
  • Phenethylamine
  • Aralkylamine
  • 4-aminopiperidine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of cancer patients with severe pain that breaks through their regular narcotic therapy.
PharmacodynamicsFentanyl 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.
Mechanism of actionOpiate 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.
AbsorptionBioavailability is 92% following transdermal administration and 50% following buccal administration.
Volume of distribution
  • 3 to 8 L/kg [Surgical Patients]
  • 0.8 to 8 [Hepatically Impaired Patients]
Protein binding80-85%
Metabolism

Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system.

SubstrateEnzymesProduct
Fentanyl
norfentanylDetails
Route of eliminationFentanyl 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.
Half life7 hours (range 3-12)
Clearance
  • 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]
ToxicityFentanyl 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.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Fentanyl Action PathwayDrug actionSMP00415
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.9901
Caco-2 permeable+0.6459
P-glycoprotein substrateSubstrate0.6082
P-glycoprotein inhibitor IInhibitor0.7161
P-glycoprotein inhibitor IINon-inhibitor0.8371
Renal organic cation transporterInhibitor0.5824
CYP450 2C9 substrateNon-substrate0.7879
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.5856
CYP450 1A2 substrateNon-inhibitor0.7715
CYP450 2C9 substrateNon-inhibitor0.873
CYP450 2D6 substrateNon-inhibitor0.6327
CYP450 2C19 substrateNon-inhibitor0.5724
CYP450 3A4 substrateNon-inhibitor0.8218
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7346
Ames testNon AMES toxic0.8417
CarcinogenicityNon-carcinogens0.8536
BiodegradationNot ready biodegradable0.8554
Rat acute toxicity3.9836 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.796
hERG inhibition (predictor II)Inhibitor0.6791
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
  • Actavis southatlantic llc
  • Lavipharm laboratories inc
  • Mylan technologies inc
  • Noven pharmaceuticals inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Meda pharmaceuticals inc
  • Abbott laboratories hosp products div
  • Hospira inc
  • Baxter healthcare corp anesthesia and critical care
  • Marsam pharmaceuticals llc
  • Akorn inc
  • Cephalon inc
  • Barr laboratories inc
  • Mallinckrodt inc
  • Incline therapeutics inc
  • Abbott laboratories
Packagers
Dosage forms
FormRouteStrength
Injectionintramuscular; intravenous50 ug/mL
Injectionintravenous50 ug/mL
Injection, solutionintramuscular; intravenous50 ug/mL
Lozengeoral; transmucosal1200 ug
Lozengeoral; transmucosal1600 ug
Lozengeoral; transmucosal200 ug
Lozengeoral; transmucosal400 ug
Lozengeoral; transmucosal600 ug
Lozengeoral; transmucosal800 ug
Lozengetransmucosal1200 ug
Lozengetransmucosal1600 ug
Lozengetransmucosal200 ug
Lozengetransmucosal400 ug
Lozengetransmucosal600 ug
Lozengetransmucosal800 ug
Patchtransdermal1.28 mg/[USP'U]
Patchtransdermal10.2 mg/[USP'U]
Patchtransdermal100 ug/h
Patchtransdermal12 ug
Patchtransdermal12 ug/h
Patchtransdermal12.5 ug/h
Patchtransdermal2.55 mg/[USP'U]
Patchtransdermal25 ug/h
Patchtransdermal5.1 mg/[USP'U]
Patchtransdermal50 ug/h
Patchtransdermal7.65 mg/[USP'U]
Patchtransdermal75 ug/h
Patch, extended releasetransdermal10 mg/72h
Patch, extended releasetransdermal100 ug/h
Patch, extended releasetransdermal2.5 mg/72h
Patch, extended releasetransdermal25 ug/h
Patch, extended releasetransdermal5 mg/72h
Patch, extended releasetransdermal50 ug/h
Patch, extended releasetransdermal7.5 mg/72h
Patch, extended releasetransdermal75 ug/h
Spraynasal100 ug
Spraynasal400 ug
Spraysublingual.1 mg
Spraysublingual.2 mg
Spraysublingual.4 mg
Spraysublingual.6 mg
Spraysublingual.8 mg
Tabletsublingual100 ug
Tabletsublingual200 ug
Tabletsublingual300 ug
Tabletsublingual400 ug
Tabletsublingual600 ug
Tabletsublingual800 ug
Prices
Unit descriptionCostUnit
Fentanyl base powder1498.18USD g
Fentanyl citrate powder1062.5USD g
Duragesic-100 5 100 mcg/hr Patches Box411.59USD box
Duragesic-75 5 75 mcg/hr Patches Box318.93USD box
Fentanyl 5 100 mcg/hr Patches Box210.0USD box
Duragesic-50 5 50 mcg/hr Patches Box205.78USD box
Actiq 1600 mcg lozenge150.29USD lozenge
Fentanyl 5 50 mcg/hr Patches Box129.99USD box
Actiq 1200 mcg lozenge121.82USD lozenge
Actiq 1600 mcg Lollipop119.42USD lollipop
Duragesic-25 5 25 mcg/hr Patches Box114.42USD box
Duragesic-12 5 12 mcg/hr Patches Box95.99USD box
Actiq 800 mcg lozenge93.76USD lozenge
Actiq 1200 mcg Lollipop85.7USD lollipop
Duragesic 100 mcg/hr patch81.36USD patch
Actiq 600 mcg lozenge79.16USD lozenge
Actiq 800 mcg Lollipop75.98USD lollipop
Fentanyl 5 12 (12.5)mcg/hr Patches Box67.99USD box
Fentanyl 5 25 mcg/hr Patches Box66.66USD box
Actiq 600 mcg Lollipop65.13USD lollipop
Actiq 400 mcg lozenge64.62USD lozenge
Fentanyl 100 mcg/hr patch61.69USD patch
Duragesic 75 mcg/hr patch61.3USD patch
Fentora 800 mcg buccal tablet54.77USD tablet
Actiq 400 mcg Lollipop53.75USD lollipop
Actiq 200 mcg lozenge51.05USD lozenge
Fentora 600 mcg buccal tablet47.37USD tablet
Fentanyl 75 mcg/hr patch46.48USD patch
Actiq 200 mcg Lollipop42.14USD lollipop
Duragesic 50 mcg/hr patch40.19USD patch
FentaNYL Citrate 1600 mcg Lollipop38.53USD lollipop
Fentora 400 mcg buccal tablet34.24USD tablet
Fentanyl 50 mcg/hr patch30.47USD patch
FentaNYL Citrate 1200 mcg Lollipop30.0USD lollipop
Fentora 300 mcg buccal tablet28.84USD tablet
Fentora 200 mcg buccal tablet23.57USD tablet
Duragesic 25 mcg/hr patch21.98USD patch
FentaNYL Citrate 400 mcg Lollipop20.0USD lollipop
Fentora 100 mcg buccal tablet18.64USD tablet
Duragesic 12 mcg/hr patch18.21USD patch
Fentanyl 25 mcg/hr patch16.67USD patch
Fentanyl 12 mcg/hr patch13.8USD patch
Fentanyl 0.05 mg/ml vial1.96USD ml
Fentanyl cit 1500 mcg/30 ml1.44USD ml
Fentanyl-ns 50 mcg/ml syringe1.0USD ml
Fentanyl-ns 300 mcg/30 ml syr0.99USD ml
Fentanyl-ns 20 mcg/ml syringe0.72USD ml
Fentanyl-ns 10 mcg/ml syringe0.64USD ml
Fentanyl cit 2750 mcg/55 ml0.35USD ml
Fentanyl-ns 500 mcg/50 ml syr0.31USD ml
Sublimaze 0.05 mg/ml ampul0.23USD ml
Fentanyl 0.05 mg/ml ampul0.21USD ml
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Patents
CountryPatent NumberApprovedExpires (estimated)
United States63176291995-06-022012-06-02
United States69759022004-04-012024-04-01
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point83-84 US. Patent 3,141,823.
water solubility200 mg/L (at 25 °C)ROY,SD & FLYNN,GL (1988)
logP4.05SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.024 mg/mLALOGPS
logP4.12ALOGPS
logP3.82ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.48 m3·mol-1ChemAxon
Polarizability40.03 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraMS
References
Synthesis Reference

Mark Rubino, “Process of making fentanyl intermediates.” U.S. Patent US20060100438, issued May 11, 2006.

US20060100438
General Reference
  1. Van Bever WF, Niemegeers CJ, Janssen PA: Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-(3-methyl-1-(2-phenylethyl)-4-piperidyl)-N-phenylpropanamide and N-(3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl)-N-phenylpropanamide. J Med Chem. 1974 Oct;17(10):1047-51. Pubmed
  2. Messina J, Darwish M, Fine PG: Fentanyl buccal tablet. Drugs Today (Barc). 2008 Jan;44(1):41-54. Pubmed
  3. Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. Pubmed
  4. Simpson DM, Messina J, Xie F, Hale M: Fentanyl buccal tablet for the relief of breakthrough pain in opioid-tolerant adult patients with chronic neuropathic pain: a multicenter, randomized, double-blind, placebo-controlled study. Clin Ther. 2007 Apr;29(4):588-601. Pubmed
External Links
ATC CodesN01AH01N02AB03
AHFS Codes
  • 28:08.08
PDB EntriesNot Available
FDA labelDownload (507 KB)
MSDSDownload (75.5 KB)
Interactions
Drug Interactions
Drug
AlvimopanIncreases levels by receptor binding competition. Discontinue opioid administration at least 7 days prior to administrating Alvimopan.
AmiodaronePossible bradycardia, hypotension
AmprenavirThe protease inhibitor, amprenavir, may increase the effect and toxicity of fentanyl.
BicalutamideCYP3A4 Inhibitors like bicalutamide may increase the serum concentration of fentanyl. The risk of prolonged adverse effects, including potentially fatal respiratory depression is increased. Consider therapy modification.
CimetidineCimetidine, a moderate CYP3A4 inhibitor, may decrease the metabolism of fentanyl. Closely monitor changes in the therapeutic and adverse effects of fentanyl if cimetidine is initiated, discontinued or dose changed.
ClotrimazoleCYP3A4 Inhibitors (Moderate) such as clotrimazole may increase the serum concentration of fentanyl. Concurrent use of fentanyl with any CYP3A4 inhibitor may result in increased fentanyl concentrations and could increase or prolong adverse effects, including potentially fatal respiratory depression. Patients receiving fentanyl and any CYP3A4 inhibitor should be closely monitored for several days following initiation of the combination, and fentanyl dosage reductions should be made as appropriate.
ConivaptanCYP3A4 Inhibitors (Strong) may increase the serum concentration of Fentanyl. Concurrent use of fentanyl with any CYP3A4 inhibitor may result in increased fentanyl concentrations and could increase or prolong adverse effects, including potentially fatal respiratory depression. Patients receiving fentanyl and any CYP3A4 inhibitor should be closely monitored for several days following initiation of the combination, and fentanyl dosage reductions should be made as appropriate.
EltrombopagIncreases levels of Fentanyl via metabolism decrease. UDP-glucuronosyltransferase inhibition.
FluconazoleFluconazole may increase levels/toxicity of fentanyl.
FosamprenavirThe protease inhibitor, fosamprenavir, may increase the effect and toxicity of fentanyl.
IndinavirThe protease inhibitor, indinavir, may increase the effect and toxicity of fentanyl.
ItraconazoleItraconazole may increase levels/toxicity of fentanyl.
KetoconazoleKetoconazole may increase levels/toxicity of fentanyl.
NelfinavirThe protease inhibitor, nelfinavir, may increase the effect and toxicity of fentanyl.
RifampicinRifampin may decrease the serum level and therapeutic effect of fentanyl.
RitonavirRitonavir increases the effect and toxicity of fentanyl/alfentanyl
RotigotinePharmacodynamic synergism may increase the effects of rotigotine. Monitor therapy closely.
SaquinavirThe protease inhibitor, saquinavir, may increase the effect and toxicity of fentanyl.
TelithromycinTelithromycin may reduce clearance of Fentanyl. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Fentanyl if Telithromycin is initiated, discontinued or dose changed.
TranylcyprominePossible increased risk of serotonin syndrome.
TriprolidineThe CNS depressants, Triprolidine and Fentanyl, may increase adverse/toxic effects due to additivity. Monitor for increased CNS depressant effects during concomitant therapy.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of fentanyl by decreasing its metabolism. Adverse effects include life-threatening respiratory depression. Monitor for changes in the therapeutic and adverse effects of fentanyl if voriconazole is initiated, discontinued or dose changed.
Food Interactions
  • Avoid alcohol.

Targets

1. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. You HJ, Colpaert FC, Arendt-Nielsen L: The novel analgesic and high-efficacy 5-HT1A receptor agonist F 13640 inhibits nociceptive responses, wind-up, and after-discharges in spinal neurons and withdrawal reflexes. Exp Neurol. 2005 Jan;191(1):174-83. Pubmed
  2. Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. Pubmed
  3. Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. Pubmed
  4. Dosen-Micovic L, Ivanovic M, Micovic V: Steric interactions and the activity of fentanyl analogs at the mu-opioid receptor. Bioorg Med Chem. 2006 May 1;14(9):2887-95. Epub 2006 Jan 11. Pubmed
  5. Dardonville C, Fernandez-Fernandez C, Gibbons SL, Ryan GJ, Jagerovic N, Gabilondo AM, Meana JJ, Callado LF: Synthesis and pharmacological studies of new hybrid derivatives of fentanyl active at the mu-opioid receptor and I2-imidazoline binding sites. Bioorg Med Chem. 2006 Oct 1;14(19):6570-80. Epub 2006 Jun 23. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Hajiha M, DuBord MA, Liu H, Horner RL: Opioid receptor mechanisms at the hypoglossal motor pool and effects on tongue muscle activity in vivo. J Physiol. 2009 Jun 1;587(Pt 11):2677-92. Epub 2009 Apr 29. Pubmed

2. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

References:

  1. Rodrigues AR, Castro MS, Francischi JN, Perez AC, Duarte ID: Participation of ATP-sensitive K+ channels in the peripheral antinociceptive effect of fentanyl in rats. Braz J Med Biol Res. 2005 Jan;38(1):91-7. Epub 2005 Jan 18. Pubmed
  2. Poonawala T, Levay-Young BK, Hebbel RP, Gupta K: Opioids heal ischemic wounds in the rat. Wound Repair Regen. 2005 Mar-Apr;13(2):165-74. Pubmed
  3. Sahin AS, Duman A, Atalik EK, Ogun CO, Sahin TK, Erol A, Ozergin U: The mechanisms of the direct vascular effects of fentanyl on isolated human saphenous veins in vitro. J Cardiothorac Vasc Anesth. 2005 Apr;19(2):197-200. Pubmed
  4. Darwish M, Tempero K, Kirby M, Thompson J: Pharmacokinetics and dose proportionality of fentanyl effervescent buccal tablets in healthy volunteers. Clin Pharmacokinet. 2005;44(12):1279-86. Pubmed
  5. Darwish M, Kirby M, Robertson P Jr, Tracewell W, Jiang JG: Pharmacokinetic properties of fentanyl effervescent buccal tablets: a phase I, open-label, crossover study of single-dose 100, 200, 400, and 800 microg in healthy adult volunteers. Clin Ther. 2006 May;28(5):707-14. Pubmed
  6. Hajiha M, DuBord MA, Liu H, Horner RL: Opioid receptor mechanisms at the hypoglossal motor pool and effects on tongue muscle activity in vivo. J Physiol. 2009 Jun 1;587(Pt 11):2677-92. Epub 2009 Apr 29. Pubmed

3. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Pascoe JE, Williams KL, Mukhopadhyay P, Rice KC, Woods JH, Ko MC: Effects of mu, kappa, and delta opioid receptor agonists on the function of hypothalamic-pituitary-adrenal axis in monkeys. Psychoneuroendocrinology. 2008 May;33(4):478-86. Epub 2008 Mar 5. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  3. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. Pubmed

2. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Wandel C, Kim R, Wood M, Wood A: Interaction of morphine, fentanyl, sufentanil, alfentanil, and loperamide with the efflux drug transporter P-glycoprotein. Anesthesiology. 2002 Apr;96(4):913-20. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12