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Identification
NameFentanyl
Accession NumberDB00813  (APRD00347, DB05853)
TypeSmall Molecule
GroupsApproved, Illicit, Investigational, Vet Approved
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
1-Phenethyl-4-(N-phenylpropionamido)piperidine
1-Phenethyl-4-N-propionylanilinopiperidine
Fentanil
Fentanila
Fentanilo
Fentanyl
Fentanyl
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
External Identifiers
  • McN-JR 4263-49
  • R 4263
  • R 5240
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Abstraltablet200 ug/1sublingualPro Strakan, Inc.2011-01-072016-04-05Us
Abstraltablet400 mcgsublingualPaladin Labs Inc2011-04-18Not applicableCanada
Abstraltablet300 ug/1sublingualGalena Biopharma, Inc.2013-08-082016-04-05Us
Abstraltablet300 mcgsublingualPaladin Labs Inc2011-04-18Not applicableCanada
Abstraltablet100 ug/1sublingualPro Strakan, Inc.2011-01-072016-04-05Us
Abstraltablet200 ug/1sublingualGalena Biopharma, Inc.2013-08-082016-04-05Us
Abstraltablet200 mcgsublingualPaladin Labs Inc2011-04-18Not applicableCanada
Abstraltablet100 ug/1sublingualGalena Biopharma, Inc.2013-08-082016-04-05Us
Abstraltablet100 mcgsublingualPaladin Labs Inc2011-04-18Not applicableCanada
Abstraltablet800 ug/1sublingualPro Strakan, Inc.2011-01-072016-04-05Us
Abstraltablet800 ug/1sublingualGalena Biopharma, Inc.2013-08-082016-04-05Us
Abstraltablet600 ug/1sublingualPro Strakan, Inc.2011-01-072016-04-05Us
Abstraltablet400 ug/1sublingualPro Strakan, Inc.2011-01-072016-04-05Us
Abstraltablet800 mcgsublingualPaladin Labs Inc2011-06-03Not applicableCanada
Abstraltablet600 ug/1sublingualGalena Biopharma, Inc.2013-08-082016-04-05Us
Abstraltablet300 ug/1sublingualPro Strakan, Inc.2011-01-072016-04-05Us
Abstraltablet600 mcgsublingualPaladin Labs Inc2011-06-14Not applicableCanada
Abstraltablet400 ug/1sublingualGalena Biopharma, Inc.2013-08-082016-04-05Us
Actiqlozenge1200 ug/1oral; transmucosalCephalon, Incorporated1998-11-042016-04-05Us
Actiqlozenge800 ug/1oral; transmucosalCephalon, Incorporated1998-11-042016-04-05Us
Actiqlozenge600 ug/1oral; transmucosalCephalon, Incorporated1998-11-042016-04-05Us
Actiqlozenge400 ug/1oral; transmucosalCephalon, Incorporated1998-11-042016-04-05Us
Actiqlozenge200 ug/1oral; transmucosalCephalon, Incorporated1998-11-042016-04-05Us
Actiqlozenge1600 ug/1oral; transmucosalCephalon, Incorporated1998-11-042016-04-05Us
Co Fentanylpatch100 mcgtransdermalCobalt Pharmaceuticals Company2012-10-18Not applicableCanada
Co Fentanylpatch75 mcgtransdermalCobalt Pharmaceuticals Company2012-10-18Not applicableCanada
Co Fentanylpatch50 mcgtransdermalCobalt Pharmaceuticals Company2012-10-18Not applicableCanada
Co Fentanylpatch25 mcgtransdermalCobalt Pharmaceuticals Company2012-10-18Not applicableCanada
Co Fentanylpatch37 mcgtransdermalCobalt Pharmaceuticals CompanyNot applicableNot applicableCanada
Co Fentanylpatch12 mcgtransdermalCobalt Pharmaceuticals Company2012-10-18Not applicableCanada
Duragesicpatch75 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-072016-04-05Us
Duragesicpatch100 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-072016-04-05Us
Duragesicpatch50 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-072016-04-05Us
Duragesicpatch25 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-072016-04-05Us
Duragesicpatch12.5 ug/htransdermalJanssen Pharmaceuticals, Inc.1990-08-072016-04-05Us
Duragesic 100patch100 mcgtransdermalJanssen Inc1992-12-312009-11-24Canada
Duragesic 12patch12 mcgtransdermalJanssen Inc2006-08-012009-11-24Canada
Duragesic 25patch25 mcgtransdermalJanssen Inc1992-12-312009-11-24Canada
Duragesic 50patch50 mcgtransdermalJanssen Inc1992-12-312009-11-24Canada
Duragesic 75patch75 mcgtransdermalJanssen Inc1992-12-312009-11-24Canada
Duragesic Matpatch100 mcgtransdermalJanssen Inc2009-05-11Not applicableCanada
Duragesic Matpatch12.0 mcgtransdermalJanssen Inc2010-03-16Not applicableCanada
Duragesic Matpatch75 mcgtransdermalJanssen Inc2009-05-11Not applicableCanada
Duragesic Matpatch50 mcgtransdermalJanssen Inc2009-05-11Not applicableCanada
Duragesic Matpatch25 mcgtransdermalJanssen Inc2009-05-11Not applicableCanada
Fentanylpatch12.5 ug/htransdermalSandoz,Inc.2004-10-012016-04-05Us
Fentanylpatch12.5 ug/htransdermalbryant ranch prepack2004-10-012016-04-05Us
Fentanylpatch100 ug/htransdermalSandoz,Inc.2004-10-012016-04-05Us
Fentanylpatch75 ug/htransdermalSandoz,Inc.2004-10-012016-04-05Us
Fentanylpatch12 ug/1transdermalDispensing Solutions, Inc.2004-10-012016-04-05Us
Fentanylpatch50 ug/htransdermalSandoz,Inc.2004-10-012016-04-05Us
Fentanylpatch25 ug/htransdermalSandoz,Inc.2004-10-012016-04-05Us
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousAkorn, Inc.2012-03-222016-04-05Us
Fentanyl Citratelozenge200 ug/1oral; transmucosalTeva Pharmaceuticals USA Inc2015-11-182016-04-23Us
Fentanyl Citratelozenge1200 ug/1oral; transmucosalPhysicians Total Care, Inc.2009-06-052016-04-05Us
Fentanyl Citrateinjection, solution5 ug/mLintravenousCantrell Drug Company2013-11-222016-04-05Us
Fentanyl Citratelozenge200 ug/1oral; transmucosalCima Labs Inc.1999-01-202017-11-30Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousHospira, Inc.1985-01-122016-04-23Us
Fentanyl Citratelozenge800 ug/1oral; transmucosalPhysicians Total Care, Inc.2009-04-242016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintravenousCantrell Drug Company2013-03-142016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousHospira, Inc.1985-01-122016-04-23Us
Fentanyl Citratelozenge600 ug/1oral; transmucosalPhysicians Total Care, Inc.2009-04-242016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintravenousCantrell Drug Company2011-10-202016-04-05Us
Fentanyl Citratelozenge1600 ug/1oral; transmucosalTeva Pharmaceuticals USA Inc2015-11-182016-04-23Us
Fentanyl Citratelozenge200 ug/1oral; transmucosalPhysicians Total Care, Inc.2009-04-242016-04-05Us
Fentanyl Citrateinjection, solution25 ug/mLintravenousCantrell Drug Company2012-10-192016-04-05Us
Fentanyl Citratelozenge1600 ug/1oral; transmucosalCima Labs Inc.1999-01-202016-10-31Us
Fentanyl Citratelozenge400 ug/1oral; transmucosalPhysicians Total Care, Inc.2008-12-192016-04-05Us
Fentanyl Citrateinjection, solution20 ug/mLintravenousCantrell Drug Company2013-01-302016-04-05Us
Fentanyl Citratelozenge1200 ug/1oral; transmucosalCima Labs Inc.1999-01-202016-11-30Us
Fentanyl Citratelozenge1200 ug/1oral; transmucosalTeva Pharmaceuticals USA Inc2015-11-182016-04-23Us
Fentanyl Citrateinjection, solution10 ug/mLintravenousCantrell Drug Company2011-07-262016-04-05Us
Fentanyl Citratelozenge800 ug/1oral; transmucosalCima Labs Inc.1999-01-202017-12-31Us
Fentanyl Citratelozenge800 ug/1oral; transmucosalTeva Pharmaceuticals USA Inc2015-11-182016-04-23Us
Fentanyl Citratelozenge600 ug/1oral; transmucosalTeva Pharmaceuticals USA Inc2015-11-182016-04-23Us
Fentanyl Citratelozenge600 ug/1oral; transmucosalCima Labs Inc.1999-01-202016-10-31Us
Fentanyl Citratelozenge400 ug/1oral; transmucosalTeva Pharmaceuticals USA Inc2015-11-182016-04-23Us
Fentanyl Citratelozenge400 ug/1oral; transmucosalCima Labs Inc.1999-01-202016-10-31Us
Fentanyl Citrate Injectionsolution50 mcgintramuscular; intravenous; epiduralHospira Healthcare Corporation1989-12-31Not applicableCanada
Fentanyl Citrate Injection Sdzliquid50 mcgintramuscular; intravenous; epiduralSandoz Canada Incorporated2013-02-21Not applicableCanada
Fentanyl Citrate Injection U.S.P.-liq IV Im Epdsolution50 mcgintramuscular; intravenous; epiduralHospira Healthcare Corporation1997-07-302011-08-05Canada
Fentanyl Citrate Injection USPsolution50 mcgintramuscular; intravenous; epiduralAlveda Pharmaceuticals IncNot applicableNot applicableCanada
Fentanyl Citrate Injection USPliquid50 mcgintramuscular; intravenous; epiduralSandoz Canada Incorporated2000-02-10Not applicableCanada
Fentanyl Citrate Injection USP 50mcg/mlliquid50 mcgintramuscular; intravenous; epiduralDavid Bull Laboratories (Canada) Inc.1993-12-311999-08-04Canada
Fentanyl Patchpatch100 mcgtransdermalPro Doc Limitee2012-11-22Not applicableCanada
Fentanyl Patchpatch75 mcgtransdermalPro Doc Limitee2012-11-22Not applicableCanada
Fentanyl Patchpatch50 mcgtransdermalPro Doc Limitee2012-11-22Not applicableCanada
Fentanyl Patchpatch25 mcgtransdermalPro Doc Limitee2012-11-22Not applicableCanada
Fentanyl Patchpatch12 mcgtransdermalPro Doc Limitee2012-11-22Not applicableCanada
Fentanyl Transdermal System 100patch (extended release)100 mcgtransdermalActavis Group Ptc EhfNot applicableNot applicableCanada
Fentanyl Transdermal System 25patch (extended release)25 mcgtransdermalActavis Group Ptc EhfNot applicableNot applicableCanada
Fentanyl Transdermal System 50patch (extended release)50 mcgtransdermalActavis Group Ptc EhfNot applicableNot applicableCanada
Fentanyl Transdermal System 75patch (extended release)75 mcgtransdermalActavis Group Ptc EhfNot applicableNot applicableCanada
Fentoratablet800 ug/1buccal; oral; transmucosalCephalon, Inc.2006-09-252016-04-05Us
Fentoratablet (effervescent)200 mcgbuccal; sublingualTeva Canada Limited2014-05-14Not applicableCanada
Fentoratablet600 ug/1buccal; oral; transmucosalCephalon, Inc.2006-09-252016-04-05Us
Fentoratablet400 ug/1buccal; oral; transmucosalCephalon, Inc.2006-09-252016-04-05Us
Fentoratablet200 ug/1buccal; oral; transmucosalCephalon, Inc.2006-09-252016-04-05Us
Fentoratablet100 ug/1buccal; oral; transmucosalCephalon, Inc.2006-09-252016-04-05Us
Fentoratablet (effervescent)800 mcgbuccal; sublingualTeva Canada Limited2014-05-14Not applicableCanada
Fentoratablet (effervescent)100 mcgbuccal; sublingualTeva Canada Limited2014-05-14Not applicableCanada
Fentoratablet (effervescent)600 mcgbuccal; sublingualTeva Canada Limited2014-05-14Not applicableCanada
Fentoratablet (effervescent)400 mcgbuccal; sublingualTeva Canada Limited2014-05-14Not applicableCanada
Instanylsolution100 mcgnasalTakeda Canada IncNot applicableNot applicableCanada
Instanylsolution200 mcgnasalTakeda Canada IncNot applicableNot applicableCanada
Instanylsolution50 mcgnasalTakeda Canada IncNot applicableNot applicableCanada
Ionsyspatch40 ug/1transdermalThe Medicines Company2015-06-012016-04-05Us
Lazandaspray300 ug/1nasalDepomed, Inc.2016-01-012016-04-05Us
Lazandaspray400 ug/1nasalDepomed, Inc.2011-10-172016-04-05Us
Lazandaspray100 ug/1nasalDepomed, Inc.2011-10-172016-04-05Us
Lazandaspray400 ug/1nasalArchimedes Pharma US Inc.2011-10-172016-04-05Us
Lazandaspray100 ug/1nasalArchimedes Pharma US Inc.2011-10-172016-04-05Us
Mylan-fentanyl Matrix Patchpatch50 mcgtransdermalMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Mylan-fentanyl Matrix Patchpatch75 mcgtransdermalMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Mylan-fentanyl Matrix Patchpatch25 mcgtransdermalMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Mylan-fentanyl Matrix Patchpatch12 mcgtransdermalMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Mylan-fentanyl Matrix Patchpatch100 mcgtransdermalMylan Pharmaceuticals Ulc2012-11-20Not applicableCanada
Onsolisfilm, soluble400 mcgbuccalMeda Ab2011-08-222013-01-31Canada
Onsolisfilm, soluble600 mcgbuccalMeda Ab2011-08-222013-01-31Canada
Onsolisfilm, soluble200 mcgbuccalMeda Ab2011-08-222013-01-31Canada
Onsolisfilm, soluble1200 mcgbuccalMeda Ab2011-08-222013-01-31Canada
Onsolisfilm, soluble800 mcgbuccalMeda Ab2011-08-222013-01-31Canada
Pat-fentanyl Matpatch25 mcgtransdermalPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-fentanyl Matpatch12.0 mcgtransdermalPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-fentanyl Matpatch100 mcgtransdermalPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-fentanyl Matpatch75 mcgtransdermalPatriot A Division Of Janssen IncNot applicableNot applicableCanada
Pat-fentanyl Matpatch50 mcgtransdermalPatriot A Division Of Janssen IncNot applicableNot applicableCanada
PMS-fentanyl Mtxpatch100 mcgtransdermalPharmascience Inc2010-03-18Not applicableCanada
PMS-fentanyl Mtxpatch75 mcgtransdermalPharmascience Inc2010-03-18Not applicableCanada
PMS-fentanyl Mtxpatch50 mcgtransdermalPharmascience Inc2010-03-18Not applicableCanada
PMS-fentanyl Mtxpatch25 mcgtransdermalPharmascience Inc2010-03-18Not applicableCanada
PMS-fentanyl Mtxpatch12 mcgtransdermalPharmascience Inc2010-03-18Not applicableCanada
Ran-fentanyl Matrix Patchpatch100 mcgtransdermalRanbaxy Pharmaceuticals Canada Inc.2009-09-28Not applicableCanada
Ran-fentanyl Matrix Patchpatch75 mcgtransdermalRanbaxy Pharmaceuticals Canada Inc.2009-09-28Not applicableCanada
Ran-fentanyl Matrix Patchpatch50 mcgtransdermalRanbaxy Pharmaceuticals Canada Inc.2009-09-28Not applicableCanada
Ran-fentanyl Matrix Patchpatch25 mcgtransdermalRanbaxy Pharmaceuticals Canada Inc.2009-09-28Not applicableCanada
Ran-fentanyl Matrix Patchpatch12 mcgtransdermalRanbaxy Pharmaceuticals Canada Inc.2009-09-28Not applicableCanada
Ran-fentanyl Transdermal Systempatch10 mgtransdermalRanbaxy Pharmaceuticals Canada Inc.2006-07-112011-08-12Canada
Ran-fentanyl Transdermal Systempatch7.5 mgtransdermalRanbaxy Pharmaceuticals Canada Inc.2006-07-112011-08-12Canada
Ran-fentanyl Transdermal Systempatch5 mgtransdermalRanbaxy Pharmaceuticals Canada Inc.2006-07-112011-08-12Canada
Ran-fentanyl Transdermal Systempatch2.5 mgtransdermalRanbaxy Pharmaceuticals Canada Inc.2006-07-112011-08-12Canada
Sandoz Fentanyl Patchpatch37 mcgtransdermalSandoz Canada Incorporated2010-11-01Not applicableCanada
Sandoz Fentanyl Patchpatch50 mcgtransdermalSandoz Canada Incorporated2010-11-01Not applicableCanada
Sandoz Fentanyl Patchpatch25 mcgtransdermalSandoz Canada Incorporated2010-11-01Not applicableCanada
Sandoz Fentanyl Patchpatch12 mcgtransdermalSandoz Canada Incorporated2010-11-01Not applicableCanada
Sandoz Fentanyl Patchpatch100 mcgtransdermalSandoz Canada Incorporated2010-11-01Not applicableCanada
Sandoz Fentanyl Patchpatch75 mcgtransdermalSandoz Canada Incorporated2010-11-01Not applicableCanada
Sublimaze Inj 50mcg/mlliquid50 mcgintramuscular; intravenous; epiduralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1987-12-311996-09-10Canada
Subsysspray.1 mg/1sublingualInsys Therapeutics, Inc.2012-03-132016-04-05Us
Subsysspray.8 mg/1sublingualInsys Therapeutics, Inc.2012-08-302016-04-05Us
Subsysspray.6 mg/1sublingualInsys Therapeutics, Inc.2012-08-302016-04-05Us
Subsysspray.8 mg/1sublingualInsys Therapeutics, Inc.2012-03-132016-04-05Us
Subsysspray.6 mg/1sublingualInsys Therapeutics, Inc.2012-03-132016-04-05Us
Subsysspray.4 mg/1sublingualInsys Therapeutics, Inc.2012-03-132016-04-05Us
Subsysspray.2 mg/1sublingualInsys Therapeutics, Inc.2012-03-132016-04-05Us
Teva-fentanylpatch12 mcgtransdermalTeva Canada Limited2008-06-27Not applicableCanada
Teva-fentanylpatch100 mcgtransdermalTeva Canada Limited2006-07-04Not applicableCanada
Teva-fentanylpatch75 mcgtransdermalTeva Canada Limited2006-07-04Not applicableCanada
Teva-fentanylpatch50 mcgtransdermalTeva Canada Limited2006-07-04Not applicableCanada
Teva-fentanylpatch25 mcgtransdermalTeva Canada Limited2006-07-04Not applicableCanada
Transmucosal Fentanyl Citratelozenge1200 1/1oral; transmucosalH.J. Harkins Company, Inc.2006-09-062016-04-05Us
Transmucosal Fentanyl Citratelozenge400 ug/1oral; transmucosalH.J. Harkins Company, Inc.2006-09-062016-04-05Us
Transmucosal Fentanyl Citratelozenge600 ug/1oral; transmucosalH.J. Harkins Company, Inc.2006-09-062016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-fentanyl Matrixpatch25 mcgtransdermalApotex Inc2009-05-13Not applicableCanada
Apo-fentanyl Matrixpatch100 mcgtransdermalApotex Inc2009-05-13Not applicableCanada
Apo-fentanyl Matrixpatch75 mcgtransdermalApotex Inc2009-05-13Not applicableCanada
Apo-fentanyl Matrixpatch50 mcgtransdermalApotex Inc2009-05-13Not applicableCanada
Fentanylpatch100 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-282016-04-23Us
Fentanylpatch, extended release25 ug/htransdermalTeva Pharmaceuticals USA Inc2008-12-222016-03-29Us
Fentanylpatch, extended release50 ug/htransdermalActavis Pharma, Inc.2007-09-012016-04-23Us
Fentanylpatch, extended release25 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch, extended release7.5 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-092016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalApotex Corp.2010-03-012016-04-05Us
Fentanylpatch, extended release50 ug/htransdermalbryant ranch prepack2013-04-042016-04-05Us
Fentanylpatch, extended release10 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-092016-04-05Us
Fentanylpatch, extended release50 ug/htransdermalbryant ranch prepack2010-03-012016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalDispensing Solutions Inc.2006-11-062016-04-05Us
Fentanylpatch, extended release50 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch, extended release75 ug/htransdermalbryant ranch prepack2013-04-042016-04-05Us
Fentanylpatch75 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-282016-04-23Us
Fentanylpatch, extended release25 ug/htransdermalActavis Pharma, Inc.2007-09-012016-04-23Us
Fentanylpatch, extended release5 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-092016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch1.28 mg/[USP'U]transdermalPhysicians Total Care, Inc.2008-11-182016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalbryant ranch prepack2013-04-042016-04-05Us
Fentanylpatch, extended release50 ug/htransdermalDIRECT RX2015-01-012016-04-05Us
Fentanylpatch, extended release75 ug/htransdermalDispensing Solutions Inc.2006-11-062016-04-05Us
Fentanylpatch50 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-282016-04-23Us
Fentanylpatch, extended release2.5 mg/72htransdermalLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-12-092016-04-05Us
Fentanylpatch, extended release75 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch10.2 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-142016-04-05Us
Fentanylpatch, extended release75 ug/htransdermalbryant ranch prepack2010-03-012016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalDIRECT RX2015-01-012016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalDispensing Solutions Inc.2006-11-062016-04-05Us
Fentanylpatch25 ug/htransdermalMylan Pharmaceuticals Inc.2005-01-282016-04-23Us
Fentanylpatch100 ug/htransdermalPar Pharmaceutical Inc.2007-08-202016-04-05Us
Fentanylpatch, extended release50 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch7.65 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-142016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalbryant ranch prepack2010-03-012016-04-05Us
Fentanylpatch100 ug/htransdermalSt. Marys Medical Park Pharmacy2011-01-262016-04-05Us
Fentanylpatch100 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-012016-04-05Us
Fentanylpatch, extended release12 ug/htransdermalApotex Corp.2016-01-222016-04-05Us
Fentanylpatch100 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2013-01-092016-04-05Us
Fentanylpatch75 ug/htransdermalPar Pharmaceutical Inc.2007-08-202016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch5.1 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-142016-04-05Us
Fentanylpatch50 ug/htransdermalSt. Marys Medical Park Pharmacy2011-01-262016-04-05Us
Fentanylpatch75 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-012016-04-05Us
Fentanylpatch, extended release75 ug/htransdermalbryant ranch prepack2007-09-012016-04-05Us
Fentanylpatch12 ug/htransdermalMylan Pharmaceuticals Inc.2007-01-242016-04-23Us
Fentanylpatch12 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2013-01-092016-04-05Us
Fentanylpatch50 ug/htransdermalPar Pharmaceutical Inc.2007-08-202016-04-05Us
Fentanylpatch, extended release5 mg/72htransdermalSTAT Rx USA LLC2007-08-202016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalApotex Corp.2010-03-012016-04-05Us
Fentanylpatch2.55 mg/[USP'U]transdermalPhysicians Total Care, Inc.2005-07-142016-04-05Us
Fentanylpatch25 ug/htransdermalSt. Marys Medical Park Pharmacy2011-01-262016-04-05Us
Fentanylpatch50 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-012016-04-05Us
Fentanylpatch, extended release50 ug/htransdermalbryant ranch prepack2007-09-012016-04-05Us
Fentanylpatch87.5 ug/htransdermalMylan Pharmaceuticals Inc.2015-02-242016-04-23Us
Fentanylpatch, extended release100 ug/htransdermalTeva Pharmaceuticals USA Inc2008-10-202016-03-29Us
Fentanylpatch, extended release100 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch, extended release75 ug/htransdermalApotex Corp.2010-03-012016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalH.J. Harkins Company, Inc.2010-03-012016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalbryant ranch prepack2010-03-012016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanylpatch25 ug/htransdermalDAVA Pharmaceuticals, Inc.2010-11-012016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalbryant ranch prepack2007-09-012016-04-05Us
Fentanylpatch62.5 ug/htransdermalMylan Pharmaceuticals Inc.2015-02-242016-04-23Us
Fentanylpatch, extended release75 ug/htransdermalTeva Pharmaceuticals USA Inc2008-10-202016-03-29Us
Fentanylpatch, extended release100 ug/htransdermalActavis Pharma, Inc.2007-09-012016-04-23Us
Fentanylpatch, extended release75 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch25 ug/htransdermalPar Pharmaceutical Inc.2007-08-202016-04-05Us
Fentanylpatch, extended release2.5 mg/72htransdermalSTAT Rx USA LLC2007-08-202016-04-05Us
Fentanylpatch50 ug/htransdermalCorium International, Inc.2007-08-202016-04-05Us
Fentanylpatch, extended release100 ug/htransdermalbryant ranch prepack2007-09-012016-04-05Us
Fentanylpatch37.5 ug/htransdermalMylan Pharmaceuticals Inc.2015-02-242016-04-23Us
Fentanylpatch, extended release50 ug/htransdermalTeva Pharmaceuticals USA Inc2008-12-222016-03-29Us
Fentanylpatch, extended release75 ug/htransdermalActavis Pharma, Inc.2007-09-012016-04-23Us
Fentanylpatch, extended release50 ug/htransdermalUpsher Smith Laboratories, Inc.2013-03-012015-12-31Us
Fentanylpatch, extended release50 ug/htransdermalApotex Corp.2010-03-012016-04-05Us
Fentanylpatch, extended release25 ug/htransdermalH.J. Harkins Company, Inc.2010-03-012016-04-05Us
Fentanylpatch, extended release75 ug/htransdermalApotex Corp.2013-04-042016-04-05Us
Fentanyl - Novapluspatch, extended release25 ug/htransdermalWatson Laboratories, Inc.2007-09-012016-04-23Us
Fentanyl - Novapluspatch, extended release50 ug/htransdermalWatson Laboratories, Inc.2007-09-012016-04-23Us
Fentanyl - Novapluspatch, extended release100 ug/htransdermalWatson Laboratories, Inc.2007-09-012016-04-23Us
Fentanyl - Novapluspatch, extended release75 ug/htransdermalWatson Laboratories, Inc.2007-09-012016-04-23Us
Fentanyl Buccaltablet800 ug/1buccal; oral; transmucosalWatson Laboratories, Inc.2011-01-072016-04-23Us
Fentanyl Buccaltablet600 ug/1buccal; oral; transmucosalWatson Laboratories, Inc.2011-01-072016-04-23Us
Fentanyl Buccaltablet400 ug/1buccal; oral; transmucosalWatson Laboratories, Inc.2011-01-072016-04-23Us
Fentanyl Buccaltablet200 ug/1buccal; oral; transmucosalWatson Laboratories, Inc.2011-01-072016-04-23Us
Fentanyl Buccaltablet100 ug/1buccal; oral; transmucosalWatson Laboratories, Inc.2011-01-072016-04-23Us
Fentanyl Citratelozenge200 ug/1transmucosalMallinckrodt Inc.2010-01-152016-04-23Us
Fentanyl Citrateinjection50 ug/mLintravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge1200 ug/1oral; transmucosalPar Pharmaceutical Inc.2011-10-172016-04-05Us
Fentanyl Citratelozenge800 ug/1oral; transmucosalLake Erie Medical DBA Quality Care Products LLC2011-10-172016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-252015-12-29Us
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge800 ug/1oral; transmucosalPar Pharmaceutical Inc.2011-10-172016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-252015-12-29Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousHospira, Inc.1991-09-242016-04-23Us
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge600 ug/1oral; transmucosalPar Pharmaceutical Inc.2011-10-172016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-252015-12-29Us
Fentanyl Citratelozenge1600 ug/1transmucosalMallinckrodt Inc.2010-01-152016-04-23Us
Fentanyl Citrateinjection50 ug/mLintravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge400 ug/1oral; transmucosalPar Pharmaceutical Inc.2011-10-172016-04-05Us
Fentanyl Citrateinjection, solution50 ug/mLintramuscular; intravenousBaxter Healthcare Corporation2010-06-252015-12-29Us
Fentanyl Citratelozenge1200 ug/1transmucosalMallinckrodt Inc.2010-01-152016-04-23Us
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge200 ug/1oral; transmucosalPar Pharmaceutical Inc.2011-10-172016-04-05Us
Fentanyl Citrateinjection50 ug/mLintramuscular; intravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge800 ug/1transmucosalMallinckrodt Inc.2010-01-152016-04-23Us
Fentanyl Citratelozenge600 ug/1transmucosalMallinckrodt Inc.2010-01-152016-04-23Us
Fentanyl Citratelozenge400 ug/1transmucosalMallinckrodt Inc.2010-01-152016-04-23Us
Fentanyl Citrateinjection50 ug/mLintravenousWest Ward Pharmaceutical Corp.1984-07-112016-04-23Us
Fentanyl Citratelozenge1600 ug/1oral; transmucosalPar Pharmaceutical Inc.2011-10-172016-04-05Us
Fentanyl Transdermal Systempatch, extended release75 ug/htransdermalMallinckrodt, Inc.2011-06-062016-04-23Us
Fentanyl Transdermal Systempatch, extended release100 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release100 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release50 ug/htransdermalMallinckrodt, Inc.2011-06-062016-04-23Us
Fentanyl Transdermal Systempatch, extended release75 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release25 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release25 ug/htransdermalMallinckrodt, Inc.2011-06-062016-04-23Us
Fentanyl Transdermal Systempatch, extended release50 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release75 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release12.5 ug/htransdermalMallinckrodt, Inc.2011-06-062016-04-23Us
Fentanyl Transdermal Systempatch, extended release25 ug/htransdermalLake Erie Medical DBA Quality Care Products LLC2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release50 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release75 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release100 ug/htransdermalMallinckrodt, Inc.2011-06-062016-04-23Us
Fentanyl Transdermal Systempatch, extended release50 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Fentanyl Transdermal Systempatch, extended release25 ug/htransdermalRebel Distributors Corp2011-02-092016-04-05Us
Fentanyl Transdermal Systempatch, extended release50 ug/htransdermalRebel Distributors Corp.2011-02-092016-04-05Us
Fentanyl Transdermal Systempatch, extended release100 ug/htransdermalbryant ranch prepack2011-06-062016-04-05Us
Over the Counter ProductsNot Available
International Brands
NameCompany
DurogesicJanssen
FentanestPfizer
NasalfentArchimedes
RapinylGedeon Richter
Brand mixtures
NameLabellerIngredients
Fentanyl Citrate, Bupivacaine HClCantrell Drug Company
Innovar InjJanssen Pharmaceutica, Division Of Janssen Ortho Inc.
Salts
Name/CASStructureProperties
Fentanyl citrate
990-73-8
Thumb
  • InChI Key: IVLVTNPOHDFFCJ-UHFFFAOYSA-N
  • Monoisotopic Mass: 528.247166138
  • Average Mass: 528.594
DBSALT000301
Fentanyl hydrochloride
ThumbNot applicableDBSALT001226
Categories
UNIIUF599785JZ
CAS number437-38-7
WeightAverage: 336.4705
Monoisotopic: 336.220163528
Chemical FormulaC22H28N2O
InChI KeyInChIKey=PJMPHNIQZUBGLI-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.
Related Articles
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 inhibitorNon-inhibitor0.873
CYP450 2D6 inhibitorNon-inhibitor0.6327
CYP450 2C19 inhibitorNon-inhibitor0.5724
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Tabletsublingual100 ug/1
Tabletsublingual100 mcg
Tabletsublingual200 ug/1
Tabletsublingual200 mcg
Tabletsublingual300 ug/1
Tabletsublingual300 mcg
Tabletsublingual400 mcg
Tabletsublingual400 ug/1
Tabletsublingual600 ug/1
Tabletsublingual600 mcg
Tabletsublingual800 ug/1
Tabletsublingual800 mcg
Patchtransdermal100 mcg
Patchtransdermal12.0 mcg
Patchtransdermal25 mcg
Patchtransdermal50 mcg
Patchtransdermal75 mcg
Patchtransdermal1.28 mg/[USP'U]
Patchtransdermal10.2 mg/[USP'U]
Patchtransdermal100 ug/h
Patchtransdermal12 ug/h
Patchtransdermal12 ug/1
Patchtransdermal12.5 ug/h
Patchtransdermal2.55 mg/[USP'U]
Patchtransdermal25 ug/h
Patchtransdermal37.5 ug/h
Patchtransdermal5.1 mg/[USP'U]
Patchtransdermal50 ug/h
Patchtransdermal62.5 ug/h
Patchtransdermal7.65 mg/[USP'U]
Patchtransdermal75 ug/h
Patchtransdermal87.5 ug/h
Patch, extended releasetransdermal10 mg/72h
Patch, extended releasetransdermal100 ug/h
Patch, extended releasetransdermal12 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
Tabletbuccal; oral; transmucosal100 ug/1
Tabletbuccal; oral; transmucosal200 ug/1
Tabletbuccal; oral; transmucosal400 ug/1
Tabletbuccal; oral; transmucosal600 ug/1
Tabletbuccal; oral; transmucosal800 ug/1
Injectionintramuscular; intravenous50 ug/mL
Injectionintravenous50 ug/mL
Injection, solutionintramuscular; intravenous50 ug/mL
Injection, solutionintravenous10 ug/mL
Injection, solutionintravenous20 ug/mL
Injection, solutionintravenous25 ug/mL
Injection, solutionintravenous5 ug/mL
Injection, solutionintravenous50 ug/mL
Lozengeoral; transmucosal1200 ug/1
Lozengeoral; transmucosal1600 ug/1
Lozengeoral; transmucosal200 ug/1
Lozengeoral; transmucosal400 ug/1
Lozengeoral; transmucosal600 ug/1
Lozengeoral; transmucosal800 ug/1
Lozengetransmucosal1200 ug/1
Lozengetransmucosal1600 ug/1
Lozengetransmucosal200 ug/1
Lozengetransmucosal400 ug/1
Lozengetransmucosal600 ug/1
Lozengetransmucosal800 ug/1
Solutionintramuscular; intravenous; epidural50 mcg
Liquidintramuscular; intravenous; epidural50 mcg
Injection, solutionepidural
Patch, extended releasetransdermal12.5 ug/h
Patch (extended release)transdermal100 mcg
Patch (extended release)transdermal25 mcg
Patch (extended release)transdermal50 mcg
Patch (extended release)transdermal75 mcg
Tablet (effervescent)buccal; sublingual100 mcg
Tablet (effervescent)buccal; sublingual200 mcg
Tablet (effervescent)buccal; sublingual400 mcg
Tablet (effervescent)buccal; sublingual600 mcg
Tablet (effervescent)buccal; sublingual800 mcg
Liquidintramuscular; intravenous
Solutionnasal100 mcg
Solutionnasal200 mcg
Solutionnasal50 mcg
Patchtransdermal40 ug/1
Spraynasal100 ug/1
Spraynasal300 ug/1
Spraynasal400 ug/1
Film, solublebuccal1200 mcg
Film, solublebuccal200 mcg
Film, solublebuccal400 mcg
Film, solublebuccal600 mcg
Film, solublebuccal800 mcg
Patchtransdermal10 mg
Patchtransdermal2.5 mg
Patchtransdermal5 mg
Patchtransdermal7.5 mg
Patchtransdermal37 mcg
Spraysublingual.1 mg/1
Spraysublingual.2 mg/1
Spraysublingual.4 mg/1
Spraysublingual.6 mg/1
Spraysublingual.8 mg/1
Patchtransdermal12 mcg
Lozengeoral; transmucosal1200 1/1
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5697896 No1996-12-162016-12-16Us
US5843014 No1995-12-012015-12-01Us
US6159498 No1996-10-182016-10-18Us
US6169920 No1998-01-022018-01-02Us
US6181963 No1999-11-022019-11-02Us
US6195582 No1999-01-282019-01-28Us
US6200604 No1999-03-262019-03-26Us
US6317629 No1995-06-022012-06-02Us
US6432440 No1998-04-202018-04-20Us
US6759059 No1999-09-242019-09-24Us
US6761910 No1999-09-242019-09-24Us
US6881208 No2002-04-192022-04-19Us
US6974590 No1999-03-262019-03-26Us
US6975902 No2004-04-012024-04-01Us
US7579019 No2000-01-222020-01-22Us
US7862832 No2008-06-152028-06-15Us
US7862833 No2008-06-152028-06-15Us
US7910132 No1999-09-242019-09-24Us
US8092832 No2004-12-302024-12-30Us
US8119158 No2004-12-302024-12-30Us
US8216604 No2004-10-032024-10-03Us
US8301238 No2011-09-302031-09-30Us
US8428708 No2012-05-212032-05-21Us
US8428709 No2012-06-112032-06-11Us
US8486972 No2010-04-272030-04-27Us
US8486973 No2010-04-272030-04-27Us
US8728441 No1999-03-262019-03-26Us
US8753611 No1999-03-262019-03-26Us
US8765100 No1999-03-262019-03-26Us
US8781571 No2012-03-312032-03-31Us
US8835459 No2007-01-252027-01-25Us
US8835460 No2007-01-252027-01-25Us
US8889176 No2004-01-162024-01-16Us
US9078814 No2004-01-082024-01-08Us
US9095706 No2013-02-032033-02-03Us
US9241935 No2007-01-252027-01-25Us
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
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-zyj0000000-7ce3a6f35f5dee98185fView in MoNA
References
Synthesis Reference

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

US20060100438
General References
  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:4420811 ]
  2. Messina J, Darwish M, Fine PG: Fentanyl buccal tablet. Drugs Today (Barc). 2008 Jan;44(1):41-54. doi: 10.1358/dot.2008.44.1.1178469. [PubMed:18301803 ]
  3. Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. [PubMed:18001263 ]
  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:17617282 ]
External Links
ATC CodesN01AH01N01AH51N02AB03
AHFS Codes
  • 28:08.08
PDB EntriesNot Available
FDA labelDownload (507 KB)
MSDSDownload (75.5 KB)
Interactions
Drug Interactions
Drug
AcepromazineAcepromazine may increase the hypotensive activities of Fentanyl.
AcetazolamideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Acetazolamide.
AcetophenazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Acetophenazine.
AlvimopanThe risk or severity of adverse effects can be increased when Fentanyl is combined with Alvimopan.
AmilorideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Amiloride.
AmisulprideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Amisulpride.
Ammonium chlorideAmmonium chloride may increase the excretion rate of Fentanyl which could result in a higher serum level.
AmphetamineAmphetamine may increase the analgesic activities of Fentanyl.
AprepitantThe serum concentration of Fentanyl can be increased when it is combined with Aprepitant.
AripiprazoleThe risk or severity of adverse effects can be increased when Fentanyl is combined with Aripiprazole.
AtazanavirThe serum concentration of Fentanyl can be increased when it is combined with Atazanavir.
AzelastineFentanyl may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
BaclofenThe risk or severity of adverse effects can be increased when Baclofen is combined with Fentanyl.
BendroflumethiazideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Bendroflumethiazide.
BenzquinamideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Benzquinamide.
BepridilFentanyl may increase the bradycardic activities of Bepridil.
BexaroteneThe serum concentration of Fentanyl can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Fentanyl can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Fentanyl can be decreased when it is combined with Bosentan.
BrimonidineBrimonidine may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
BumetanideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Bumetanide.
ButorphanolButorphanol may decrease the analgesic activities of Fentanyl.
CarbamazepineThe serum concentration of Fentanyl can be decreased when it is combined with Carbamazepine.
CarphenazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Carphenazine.
CathinoneCathinone may increase the analgesic activities of Fentanyl.
CeritinibThe serum concentration of Fentanyl can be increased when it is combined with Ceritinib.
ChlormezanoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlormezanone.
ChlorothiazideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorothiazide.
ChlorpromazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorpromazine.
ChlorprothixeneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorprothixene.
ChlorthalidoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorthalidone.
ClarithromycinThe serum concentration of Fentanyl can be increased when it is combined with Clarithromycin.
ClozapineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Clozapine.
CobicistatThe serum concentration of Fentanyl can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Fentanyl can be increased when it is combined with Conivaptan.
CrizotinibThe serum concentration of Fentanyl can be increased when it is combined with Crizotinib.
CyclothiazideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Cyclothiazide.
DabrafenibThe serum concentration of Fentanyl can be decreased when it is combined with Dabrafenib.
DapoxetineThe risk or severity of adverse effects can be increased when Dapoxetine is combined with Fentanyl.
DarunavirThe serum concentration of Fentanyl can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Fentanyl can be increased when it is combined with Dasatinib.
DelavirdineThe serum concentration of Fentanyl can be increased when it is combined with Delavirdine.
DesmopressinThe risk or severity of adverse effects can be increased when Fentanyl is combined with Desmopressin.
DexamethasoneThe serum concentration of Fentanyl can be decreased when it is combined with Dexamethasone.
DiltiazemThe serum concentration of Fentanyl can be increased when it is combined with Diltiazem.
DoxylamineDoxylamine may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
DronabinolDronabinol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
DronedaroneThe serum concentration of Fentanyl can be increased when it is combined with Dronedarone.
DroperidolDroperidol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
EfavirenzThe serum concentration of Fentanyl can be decreased when it is combined with Efavirenz.
EluxadolineFentanyl may increase the activities of Eluxadoline.
EnzalutamideThe serum concentration of Fentanyl can be decreased when it is combined with Enzalutamide.
EphedrineThe serum concentration of Fentanyl can be decreased when it is combined with Ephedrine.
ErythromycinThe serum concentration of Fentanyl can be increased when it is combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Fentanyl can be decreased when it is combined with Eslicarbazepine acetate.
Etacrynic acidThe risk or severity of adverse effects can be increased when Fentanyl is combined with Ethacrynic acid.
EthanolFentanyl may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
EthoxzolamideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Ethoxzolamide.
EtravirineThe serum concentration of Fentanyl can be decreased when it is combined with Etravirine.
FencamfamineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Fencamfamine.
FluconazoleThe serum concentration of Fentanyl can be increased when it is combined with Fluconazole.
FlupentixolThe risk or severity of adverse effects can be increased when Fentanyl is combined with Flupentixol.
FluphenazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Fluphenazine.
FluspirileneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Fluspirilene.
FluvoxamineThe risk or severity of adverse effects can be increased when Fluvoxamine is combined with Fentanyl.
FosamprenavirThe serum concentration of Fentanyl can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Fentanyl can be increased when it is combined with Fosaprepitant.
FosphenytoinThe serum concentration of Fentanyl can be decreased when it is combined with Fosphenytoin.
FurosemideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Furosemide.
Fusidic AcidThe serum concentration of Fentanyl can be increased when it is combined with Fusidic Acid.
GranisetronGranisetron may increase the serotonergic activities of Fentanyl.
HaloperidolThe risk or severity of adverse effects can be increased when Fentanyl is combined with Haloperidol.
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Hydrochlorothiazide.
HydrocodoneFentanyl may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
HydroflumethiazideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Hydroflumethiazide.
HydroxyzineHydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
IdelalisibThe serum concentration of Fentanyl can be increased when it is combined with Idelalisib.
ImatinibThe serum concentration of Fentanyl can be increased when it is combined with Imatinib.
IndapamideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Indapamide.
IndinavirThe serum concentration of Fentanyl can be increased when it is combined with Indinavir.
Ioflupane I 123Fentanyl may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
IsavuconazoniumThe serum concentration of Fentanyl can be increased when it is combined with Isavuconazonium.
ItraconazoleThe serum concentration of Fentanyl can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Fentanyl can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Fentanyl can be increased when it is combined with Ketoconazole.
LorazepamThe risk or severity of adverse effects can be increased when Lorazepam is combined with Fentanyl.
LoxapineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Loxapine.
LuliconazoleThe serum concentration of Fentanyl can be increased when it is combined with Luliconazole.
Magnesium SulfateMagnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
MesoridazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Mesoridazine.
MethotrimeprazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Methotrimeprazine.
MetoclopramideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Metoclopramide.
MetolazoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Metolazone.
MetyrosineFentanyl may increase the sedative activities of Metyrosine.
MifepristoneThe serum concentration of Fentanyl can be increased when it is combined with Mifepristone.
MinocyclineMinocycline may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
MitotaneThe serum concentration of Fentanyl can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Fentanyl can be decreased when it is combined with Modafinil.
MolindoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Molindone.
NabiloneNabilone may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
NadololFentanyl may increase the bradycardic activities of Nadolol.
NafcillinThe serum concentration of Fentanyl can be decreased when it is combined with Nafcillin.
NaltrexoneThe therapeutic efficacy of Fentanyl can be decreased when used in combination with Naltrexone.
NaphazolineThe serum concentration of Fentanyl can be decreased when it is combined with Naphazoline.
NefazodoneThe serum concentration of Fentanyl can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Fentanyl can be increased when it is combined with Nelfinavir.
NilotinibThe serum concentration of Fentanyl can be increased when it is combined with Nilotinib.
OlanzapineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Olanzapine.
OndansetronThe risk or severity of adverse effects can be increased when Fentanyl is combined with Ondansetron.
OrphenadrineFentanyl may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
OxymetazolineThe serum concentration of Fentanyl can be decreased when it is combined with Oxymetazoline.
PalbociclibThe serum concentration of Fentanyl can be increased when it is combined with Palbociclib.
PaliperidoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Paliperidone.
ParaldehydeFentanyl may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
PegvisomantThe therapeutic efficacy of Pegvisomant can be decreased when used in combination with Fentanyl.
PerampanelPerampanel may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
PerphenazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Perphenazine.
PhenelzineFentanyl may increase the serotonergic activities of Phenelzine.
PhenobarbitalThe serum concentration of Fentanyl can be decreased when it is combined with Phenobarbital.
PhenylephrineThe serum concentration of Fentanyl can be decreased when it is combined with Phenylephrine.
PhenytoinThe serum concentration of Fentanyl can be decreased when it is combined with Phenytoin.
PimozideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Pimozide.
PiperacetazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Piperacetazine.
PosaconazoleThe serum concentration of Fentanyl can be increased when it is combined with Posaconazole.
PramipexoleFentanyl may increase the sedative activities of Pramipexole.
PrimidoneThe serum concentration of Fentanyl can be decreased when it is combined with Primidone.
ProchlorperazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Prochlorperazine.
ProcyclidineThe risk or severity of adverse effects can be increased when Procyclidine is combined with Fentanyl.
PromazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Promazine.
PropylhexedrineThe serum concentration of Fentanyl can be decreased when it is combined with Propylhexedrine.
PseudoephedrineThe serum concentration of Fentanyl can be decreased when it is combined with Pseudoephedrine.
QuetiapineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Quetiapine.
RamosetronFentanyl may increase the activities of Ramosetron.
RemoxiprideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Remoxipride.
ReserpineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Reserpine.
RifabutinThe serum concentration of Fentanyl can be decreased when it is combined with Rifabutin.
RifampicinThe serum concentration of Fentanyl can be decreased when it is combined with Rifampicin.
RifapentineThe serum concentration of Fentanyl can be decreased when it is combined with Rifapentine.
RisperidoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Risperidone.
RitonavirThe serum concentration of Fentanyl can be increased when it is combined with Ritonavir.
RopiniroleFentanyl may increase the sedative activities of Ropinirole.
RotigotineFentanyl may increase the sedative activities of Rotigotine.
RufinamideThe risk or severity of adverse effects can be increased when Rufinamide is combined with Fentanyl.
SaquinavirThe serum concentration of Fentanyl can be increased when it is combined with Saquinavir.
SertindoleThe risk or severity of adverse effects can be increased when Fentanyl is combined with Sertindole.
SimeprevirThe serum concentration of Fentanyl can be increased when it is combined with Simeprevir.
Sodium oxybateSodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
SpironolactoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Spironolactone.
St. John's WortThe serum concentration of Fentanyl can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Fentanyl can be increased when it is combined with Stiripentol.
SuccinylcholineSuccinylcholine may increase the bradycardic activities of Fentanyl.
SulpirideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Sulpiride.
SuvorexantFentanyl may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
TapentadolTapentadol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
TelaprevirThe serum concentration of Fentanyl can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Fentanyl can be increased when it is combined with Telithromycin.
ThalidomideFentanyl may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
ThioridazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Thioridazine.
ThiothixeneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Thiothixene.
TicrynafenThe risk or severity of adverse effects can be increased when Fentanyl is combined with Ticrynafen.
TorasemideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Torasemide.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Fentanyl.
TranylcypromineFentanyl may increase the serotonergic activities of Tranylcypromine.
TriamtereneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Triamterene.
TrichlormethiazideThe risk or severity of adverse effects can be increased when Fentanyl is combined with Trichlormethiazide.
TrifluoperazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Trifluoperazine.
TriflupromazineThe risk or severity of adverse effects can be increased when Fentanyl is combined with Triflupromazine.
TriprolidineThe serum concentration of Fentanyl can be decreased when it is combined with Triprolidine.
VerapamilThe serum concentration of Fentanyl can be increased when it is combined with Verapamil.
VoriconazoleThe serum concentration of Fentanyl can be increased when it is combined with Voriconazole.
ZiprasidoneThe risk or severity of adverse effects can be increased when Fentanyl is combined with Ziprasidone.
ZolpidemFentanyl may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
ZuclopenthixolThe risk or severity of adverse effects can be increased when Fentanyl is combined with Zuclopenthixol.
Food Interactions
  • Avoid alcohol.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Voltage-gated calcium channel activity
Specific Function:
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone. Agonist binding to the receptor induces coupling to an inactive GDP-bound heterotrimeric G-protein complex and subsequent exchange of GDP for GTP in the G-protein alpha subunit leading to dissociati...
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular Weight:
44778.855 Da
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:15589524 ]
  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:16114980 ]
  3. Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149 ]
  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:16376082 ]
  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:16797997 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  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. doi: 10.1113/jphysiol.2009.171678. Epub 2009 Apr 29. [PubMed:19403616 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Opioid receptor activity
Specific Function:
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurot...
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular Weight:
40368.235 Da
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:15665994 ]
  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:15828941 ]
  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:15868528 ]
  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:16372825 ]
  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:16861092 ]
  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. doi: 10.1113/jphysiol.2009.171678. Epub 2009 Apr 29. [PubMed:19403616 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Opioid receptor activity
Specific Function:
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synthetic opioids and for the psychoactive diterpene salvinorin A. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates th...
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular Weight:
42644.665 Da
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. doi: 10.1016/j.psyneuen.2008.01.006. Epub 2008 Mar 5. [PubMed:18325678 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. 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:10490933 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
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:11964599 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on May 03, 2016 02:36