DrugBank: Fentanyl

Identification Taxonomy Pharmacology ADMET Pharmacoeconomics Properties Spectra References Interactions Targets (3)Enzymes (3)Transporters (1)Comments

Targets (3)Enzymes (3)Transporters (1)Biointeractions (8)

Identification

Name

Fentanyl

Accession Number

DB00813 (APRD00347, DB05853)

Type

Small Molecule

Groups

Approved, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

1-Phenethyl-4-(N-phenylpropionamido)piperidine

1-Phenethyl-4-N-propionylanilinopiperidine

Fentanil

Fentanila

Fentanilo

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Abstral	tablet	300 ug/1	sublingual	Galena Biopharma, Inc.	2013-08-08	2016-04-05	US
Abstral	tablet	300 mcg	sublingual	Paladin Labs Inc	2011-04-18	Not applicable	Canada
Abstral	tablet	200 ug/1	sublingual	Pro Strakan, Inc.	2011-01-07	2016-04-05	US
Abstral	tablet	400 mcg	sublingual	Paladin Labs Inc	2011-04-18	Not applicable	Canada
Abstral	tablet	200 ug/1	sublingual	Galena Biopharma, Inc.	2013-08-08	2016-04-05	US
Abstral	tablet	200 mcg	sublingual	Paladin Labs Inc	2011-04-18	Not applicable	Canada
Abstral	tablet	100 ug/1	sublingual	Pro Strakan, Inc.	2011-01-07	2016-04-05	US
Abstral	tablet	100 ug/1	sublingual	Galena Biopharma, Inc.	2013-08-08	2016-04-05	US
Abstral	tablet	100 mcg	sublingual	Paladin Labs Inc	2011-04-18	Not applicable	Canada
Abstral	tablet	800 ug/1	sublingual	Pro Strakan, Inc.	2011-01-07	2016-04-05	US
Abstral	tablet	600 ug/1	sublingual	Pro Strakan, Inc.	2011-01-07	2016-04-05	US
Abstral	tablet	800 ug/1	sublingual	Galena Biopharma, Inc.	2013-08-08	2016-04-05	US
Abstral	tablet	400 ug/1	sublingual	Pro Strakan, Inc.	2011-01-07	2016-04-05	US
Abstral	tablet	800 mcg	sublingual	Paladin Labs Inc	2011-06-03	Not applicable	Canada
Abstral	tablet	600 ug/1	sublingual	Galena Biopharma, Inc.	2013-08-08	2016-04-05	US
Abstral	tablet	400 ug/1	sublingual	Galena Biopharma, Inc.	2013-08-08	2016-04-05	US
Abstral	tablet	300 ug/1	sublingual	Pro Strakan, Inc.	2011-01-07	2016-04-05	US
Abstral	tablet	600 mcg	sublingual	Paladin Labs Inc	2011-06-14	Not applicable	Canada
Actiq	lozenge	1200 ug/1	oral; transmucosal	Cephalon, Incorporated	1998-11-04	2016-04-05	US
Actiq	lozenge	800 ug/1	oral; transmucosal	Cephalon, Incorporated	1998-11-04	2016-04-05	US
Actiq	lozenge	600 ug/1	oral; transmucosal	Cephalon, Incorporated	1998-11-04	2016-04-05	US
Actiq	lozenge	400 ug/1	oral; transmucosal	Cephalon, Incorporated	1998-11-04	2016-04-05	US
Actiq	lozenge	200 ug/1	oral; transmucosal	Cephalon, Incorporated	1998-11-04	2016-04-05	US
Actiq	lozenge	1600 ug/1	oral; transmucosal	Cephalon, Incorporated	1998-11-04	2016-04-05	US
Co Fentanyl	patch	100 mcg	transdermal	Cobalt Pharmaceuticals Company	2012-10-18	Not applicable	Canada
Co Fentanyl	patch	75 mcg	transdermal	Cobalt Pharmaceuticals Company	2012-10-18	Not applicable	Canada
Co Fentanyl	patch	50 mcg	transdermal	Cobalt Pharmaceuticals Company	2012-10-18	Not applicable	Canada
Co Fentanyl	patch	25 mcg	transdermal	Cobalt Pharmaceuticals Company	2012-10-18	Not applicable	Canada
Co Fentanyl	patch	37 mcg	transdermal	Cobalt Pharmaceuticals Company	Not applicable	Not applicable	Canada
Co Fentanyl	patch	12 mcg	transdermal	Cobalt Pharmaceuticals Company	2012-10-18	Not applicable	Canada
Duragesic	patch	100 ug/h	transdermal	Janssen Pharmaceuticals, Inc.	1990-08-07	2016-04-05	US
Duragesic	patch	75 ug/h	transdermal	Janssen Pharmaceuticals, Inc.	1990-08-07	2016-04-05	US
Duragesic	patch	50 ug/h	transdermal	Janssen Pharmaceuticals, Inc.	1990-08-07	2016-04-05	US
Duragesic	patch	25 ug/h	transdermal	Janssen Pharmaceuticals, Inc.	1990-08-07	2016-04-05	US
Duragesic	patch	12.5 ug/h	transdermal	Janssen Pharmaceuticals, Inc.	1990-08-07	2016-04-05	US
Duragesic 100	patch	100 mcg	transdermal	Janssen Inc	1992-12-31	2009-11-24	Canada
Duragesic 12	patch	12 mcg	transdermal	Janssen Inc	2006-08-01	2009-11-24	Canada
Duragesic 25	patch	25 mcg	transdermal	Janssen Inc	1992-12-31	2009-11-24	Canada
Duragesic 50	patch	50 mcg	transdermal	Janssen Inc	1992-12-31	2009-11-24	Canada
Duragesic 75	patch	75 mcg	transdermal	Janssen Inc	1992-12-31	2009-11-24	Canada
Duragesic Mat	patch	100 mcg	transdermal	Janssen Inc	2009-05-11	Not applicable	Canada
Duragesic Mat	patch	12.0 mcg	transdermal	Janssen Inc	2010-03-16	Not applicable	Canada
Duragesic Mat	patch	75 mcg	transdermal	Janssen Inc	2009-05-11	Not applicable	Canada
Duragesic Mat	patch	50 mcg	transdermal	Janssen Inc	2009-05-11	Not applicable	Canada
Duragesic Mat	patch	25 mcg	transdermal	Janssen Inc	2009-05-11	Not applicable	Canada
Fentanyl	patch	12.5 ug/h	transdermal	bryant ranch prepack	2004-10-01	2016-04-05	US
Fentanyl	patch	12.5 ug/h	transdermal	Sandoz,Inc.	2004-10-01	2016-04-05	US
Fentanyl	patch	100 ug/h	transdermal	Sandoz,Inc.	2004-10-01	2016-04-05	US
Fentanyl	patch	75 ug/h	transdermal	Sandoz,Inc.	2004-10-01	2016-04-05	US
Fentanyl	patch	50 ug/h	transdermal	Sandoz,Inc.	2004-10-01	2016-04-05	US
Fentanyl	patch	12 ug/1	transdermal	Dispensing Solutions, Inc.	2004-10-01	2016-04-05	US
Fentanyl	patch	25 ug/h	transdermal	Sandoz,Inc.	2004-10-01	2016-04-05	US
Fentanyl Citrate	lozenge	1200 ug/1	oral; transmucosal	Physicians Total Care, Inc.	2009-06-05	2016-04-05	US
Fentanyl Citrate	injection, solution	5 ug/mL	intravenous	Cantrell Drug Company	2013-11-22	2016-04-05	US
Fentanyl Citrate	lozenge	200 ug/1	oral; transmucosal	Cima Labs Inc.	1999-01-20	2017-11-30	US
Fentanyl Citrate	injection	50 ug/mL	intramuscular; intravenous	Akorn, Inc.	2012-03-22	2016-04-05	US
Fentanyl Citrate	lozenge	200 ug/1	oral; transmucosal	Teva Pharmaceuticals USA Inc	2015-11-18	Not applicable	US
Fentanyl Citrate	lozenge	800 ug/1	oral; transmucosal	Physicians Total Care, Inc.	2009-04-24	2016-04-05	US
Fentanyl Citrate	injection, solution	50 ug/mL	intravenous	Cantrell Drug Company	2013-03-14	2016-04-05	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Hospira, Inc.	1985-01-12	Not applicable	US
Fentanyl Citrate	lozenge	600 ug/1	oral; transmucosal	Physicians Total Care, Inc.	2009-04-24	2016-04-05	US
Fentanyl Citrate	injection, solution	50 ug/mL	intravenous	Cantrell Drug Company	2011-10-20	2016-04-05	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Hospira, Inc.	1985-01-12	Not applicable	US
Fentanyl Citrate	lozenge	1600 ug/1	oral; transmucosal	Teva Pharmaceuticals USA Inc	2015-11-18	Not applicable	US
Fentanyl Citrate	lozenge	200 ug/1	oral; transmucosal	Physicians Total Care, Inc.	2009-04-24	2016-04-05	US
Fentanyl Citrate	injection, solution	25 ug/mL	intravenous	Cantrell Drug Company	2012-10-19	2016-04-05	US
Fentanyl Citrate	lozenge	1600 ug/1	oral; transmucosal	Cima Labs Inc.	1999-01-20	2016-10-31	US
Fentanyl Citrate	lozenge	1200 ug/1	oral; transmucosal	Teva Pharmaceuticals USA Inc	2015-11-18	Not applicable	US
Fentanyl Citrate	lozenge	400 ug/1	oral; transmucosal	Physicians Total Care, Inc.	2008-12-19	2016-04-05	US
Fentanyl Citrate	injection, solution	20 ug/mL	intravenous	Cantrell Drug Company	2013-01-30	2016-04-05	US
Fentanyl Citrate	lozenge	1200 ug/1	oral; transmucosal	Cima Labs Inc.	1999-01-20	2016-11-30	US
Fentanyl Citrate	lozenge	800 ug/1	oral; transmucosal	Teva Pharmaceuticals USA Inc	2015-11-18	Not applicable	US
Fentanyl Citrate	injection, solution	10 ug/mL	intravenous	Cantrell Drug Company	2011-07-26	2016-04-05	US
Fentanyl Citrate	lozenge	800 ug/1	oral; transmucosal	Cima Labs Inc.	1999-01-20	2017-12-31	US
Fentanyl Citrate	lozenge	600 ug/1	oral; transmucosal	Teva Pharmaceuticals USA Inc	2015-11-18	Not applicable	US
Fentanyl Citrate	lozenge	600 ug/1	oral; transmucosal	Cima Labs Inc.	1999-01-20	2016-10-31	US
Fentanyl Citrate	lozenge	400 ug/1	oral; transmucosal	Cima Labs Inc.	1999-01-20	2016-10-31	US
Fentanyl Citrate	lozenge	400 ug/1	oral; transmucosal	Teva Pharmaceuticals USA Inc	2015-11-18	Not applicable	US
Fentanyl Citrate Injection	solution	50 mcg	intramuscular; intravenous; epidural	Hospira Healthcare Corporation	1989-12-31	Not applicable	Canada
Fentanyl Citrate Injection Sdz	liquid	50 mcg	intramuscular; intravenous; epidural	Sandoz Canada Incorporated	2013-02-21	Not applicable	Canada
Fentanyl Citrate Injection U.S.P.-liq IV Im Epd	solution	50 mcg	intramuscular; intravenous; epidural	Hospira Healthcare Corporation	1997-07-30	2011-08-05	Canada
Fentanyl Citrate Injection USP	solution	50 mcg	intramuscular; intravenous; epidural	Alveda Pharmaceuticals Inc	Not applicable	Not applicable	Canada
Fentanyl Citrate Injection USP	liquid	50 mcg	intramuscular; intravenous; epidural	Sandoz Canada Incorporated	2000-02-10	Not applicable	Canada
Fentanyl Citrate Injection USP 50mcg/ml	liquid	50 mcg	intramuscular; intravenous; epidural	David Bull Laboratories (Canada) Inc.	1993-12-31	1999-08-04	Canada
Fentanyl Patch	patch	100 mcg	transdermal	Pro Doc Limitee	2012-11-22	Not applicable	Canada
Fentanyl Patch	patch	75 mcg	transdermal	Pro Doc Limitee	2012-11-22	Not applicable	Canada
Fentanyl Patch	patch	50 mcg	transdermal	Pro Doc Limitee	2012-11-22	Not applicable	Canada
Fentanyl Patch	patch	25 mcg	transdermal	Pro Doc Limitee	2012-11-22	Not applicable	Canada
Fentanyl Patch	patch	12 mcg	transdermal	Pro Doc Limitee	2012-11-22	Not applicable	Canada
Fentanyl Transdermal System 100	patch (extended release)	100 mcg	transdermal	Actavis Group Ptc Ehf	Not applicable	Not applicable	Canada
Fentanyl Transdermal System 25	patch (extended release)	25 mcg	transdermal	Actavis Group Ptc Ehf	Not applicable	Not applicable	Canada
Fentanyl Transdermal System 50	patch (extended release)	50 mcg	transdermal	Actavis Group Ptc Ehf	Not applicable	Not applicable	Canada
Fentanyl Transdermal System 75	patch (extended release)	75 mcg	transdermal	Actavis Group Ptc Ehf	Not applicable	Not applicable	Canada
Fentora	tablet (effervescent)	200 mcg	buccal; sublingual	Teva Canada Limited	2014-05-14	Not applicable	Canada
Fentora	tablet	800 ug/1	buccal; oral; transmucosal	Cephalon, Inc.	2006-09-25	2016-04-05	US
Fentora	tablet	600 ug/1	buccal; oral; transmucosal	Cephalon, Inc.	2006-09-25	2016-04-05	US
Fentora	tablet	400 ug/1	buccal; oral; transmucosal	Cephalon, Inc.	2006-09-25	2016-04-05	US
Fentora	tablet	200 ug/1	buccal; oral; transmucosal	Cephalon, Inc.	2006-09-25	2016-04-05	US
Fentora	tablet	100 ug/1	buccal; oral; transmucosal	Cephalon, Inc.	2006-09-25	2016-04-05	US
Fentora	tablet (effervescent)	800 mcg	buccal; sublingual	Teva Canada Limited	2014-05-14	Not applicable	Canada
Fentora	tablet (effervescent)	100 mcg	buccal; sublingual	Teva Canada Limited	2014-05-14	Not applicable	Canada
Fentora	tablet (effervescent)	600 mcg	buccal; sublingual	Teva Canada Limited	2014-05-14	Not applicable	Canada
Fentora	tablet (effervescent)	400 mcg	buccal; sublingual	Teva Canada Limited	2014-05-14	Not applicable	Canada
Instanyl	solution	100 mcg	nasal	Takeda Canada Inc	Not applicable	Not applicable	Canada
Instanyl	solution	200 mcg	nasal	Takeda Canada Inc	Not applicable	Not applicable	Canada
Instanyl	solution	50 mcg	nasal	Takeda Canada Inc	Not applicable	Not applicable	Canada
Ionsys	patch	40 ug/1	transdermal	The Medicines Company	2015-06-01	2016-04-05	US
Lazanda	spray	300 ug/1	nasal	Depomed, Inc.	2016-01-01	2016-04-05	US
Lazanda	spray	400 ug/1	nasal	Depomed, Inc.	2011-10-17	2016-04-05	US
Lazanda	spray	100 ug/1	nasal	Depomed, Inc.	2011-10-17	2016-04-05	US
Lazanda	spray	400 ug/1	nasal	Archimedes Pharma US Inc.	2011-10-17	2016-04-05	US
Lazanda	spray	100 ug/1	nasal	Archimedes Pharma US Inc.	2011-10-17	2016-04-05	US
Mylan-fentanyl Matrix Patch	patch	50 mcg	transdermal	Mylan Pharmaceuticals Ulc	2012-11-20	Not applicable	Canada
Mylan-fentanyl Matrix Patch	patch	75 mcg	transdermal	Mylan Pharmaceuticals Ulc	2012-11-20	Not applicable	Canada
Mylan-fentanyl Matrix Patch	patch	25 mcg	transdermal	Mylan Pharmaceuticals Ulc	2012-11-20	Not applicable	Canada
Mylan-fentanyl Matrix Patch	patch	12 mcg	transdermal	Mylan Pharmaceuticals Ulc	2012-11-20	Not applicable	Canada
Mylan-fentanyl Matrix Patch	patch	100 mcg	transdermal	Mylan Pharmaceuticals Ulc	2012-11-20	Not applicable	Canada
Onsolis	film, soluble	600 mcg	buccal	Meda Ab	2011-08-22	2013-01-31	Canada
Onsolis	film, soluble	400 mcg	buccal	Meda Ab	2011-08-22	2013-01-31	Canada
Onsolis	film, soluble	200 mcg	buccal	Meda Ab	2011-08-22	2013-01-31	Canada
Onsolis	film, soluble	1200 mcg	buccal	Meda Ab	2011-08-22	2013-01-31	Canada
Onsolis	film, soluble	800 mcg	buccal	Meda Ab	2011-08-22	2013-01-31	Canada
Pat-fentanyl Mat	patch	25 mcg	transdermal	Patriot A Division Of Janssen Inc	Not applicable	Not applicable	Canada
Pat-fentanyl Mat	patch	12.0 mcg	transdermal	Patriot A Division Of Janssen Inc	Not applicable	Not applicable	Canada
Pat-fentanyl Mat	patch	100 mcg	transdermal	Patriot A Division Of Janssen Inc	Not applicable	Not applicable	Canada
Pat-fentanyl Mat	patch	75 mcg	transdermal	Patriot A Division Of Janssen Inc	Not applicable	Not applicable	Canada
Pat-fentanyl Mat	patch	50 mcg	transdermal	Patriot A Division Of Janssen Inc	Not applicable	Not applicable	Canada
PMS-fentanyl Mtx	patch	100 mcg	transdermal	Pharmascience Inc	2010-03-18	Not applicable	Canada
PMS-fentanyl Mtx	patch	75 mcg	transdermal	Pharmascience Inc	2010-03-18	Not applicable	Canada
PMS-fentanyl Mtx	patch	50 mcg	transdermal	Pharmascience Inc	2010-03-18	Not applicable	Canada
PMS-fentanyl Mtx	patch	25 mcg	transdermal	Pharmascience Inc	2010-03-18	Not applicable	Canada
PMS-fentanyl Mtx	patch	12 mcg	transdermal	Pharmascience Inc	2010-03-18	Not applicable	Canada
Ran-fentanyl Matrix Patch	patch	100 mcg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2009-09-28	Not applicable	Canada
Ran-fentanyl Matrix Patch	patch	75 mcg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2009-09-28	Not applicable	Canada
Ran-fentanyl Matrix Patch	patch	50 mcg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2009-09-28	Not applicable	Canada
Ran-fentanyl Matrix Patch	patch	25 mcg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2009-09-28	Not applicable	Canada
Ran-fentanyl Matrix Patch	patch	12 mcg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2009-09-28	Not applicable	Canada
Ran-fentanyl Transdermal System	patch	10 mg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2006-07-11	2011-08-12	Canada
Ran-fentanyl Transdermal System	patch	7.5 mg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2006-07-11	2011-08-12	Canada
Ran-fentanyl Transdermal System	patch	5 mg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2006-07-11	2011-08-12	Canada
Ran-fentanyl Transdermal System	patch	2.5 mg	transdermal	Ranbaxy Pharmaceuticals Canada Inc.	2006-07-11	2011-08-12	Canada
Sandoz Fentanyl Patch	patch	37 mcg	transdermal	Sandoz Canada Incorporated	2010-11-01	Not applicable	Canada
Sandoz Fentanyl Patch	patch	50 mcg	transdermal	Sandoz Canada Incorporated	2010-11-01	Not applicable	Canada
Sandoz Fentanyl Patch	patch	25 mcg	transdermal	Sandoz Canada Incorporated	2010-11-01	Not applicable	Canada
Sandoz Fentanyl Patch	patch	12 mcg	transdermal	Sandoz Canada Incorporated	2010-11-01	Not applicable	Canada
Sandoz Fentanyl Patch	patch	100 mcg	transdermal	Sandoz Canada Incorporated	2010-11-01	Not applicable	Canada
Sandoz Fentanyl Patch	patch	75 mcg	transdermal	Sandoz Canada Incorporated	2010-11-01	Not applicable	Canada
Sublimaze Inj 50mcg/ml	liquid	50 mcg	intramuscular; intravenous; epidural	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1987-12-31	1996-09-10	Canada
Subsys	spray	.1 mg/1	sublingual	Insys Therapeutics, Inc.	2012-03-13	2016-04-05	US
Subsys	spray	.8 mg/1	sublingual	Insys Therapeutics, Inc.	2012-08-30	2016-04-05	US
Subsys	spray	.6 mg/1	sublingual	Insys Therapeutics, Inc.	2012-08-30	2016-04-05	US
Subsys	spray	.8 mg/1	sublingual	Insys Therapeutics, Inc.	2012-03-13	2016-04-05	US
Subsys	spray	.6 mg/1	sublingual	Insys Therapeutics, Inc.	2012-03-13	2016-04-05	US
Subsys	spray	.4 mg/1	sublingual	Insys Therapeutics, Inc.	2012-03-13	2016-04-05	US
Subsys	spray	.2 mg/1	sublingual	Insys Therapeutics, Inc.	2012-03-13	2016-04-05	US
Teva-fentanyl	patch	12 mcg	transdermal	Teva Canada Limited	2008-06-27	Not applicable	Canada
Teva-fentanyl	patch	100 mcg	transdermal	Teva Canada Limited	2006-07-04	Not applicable	Canada
Teva-fentanyl	patch	75 mcg	transdermal	Teva Canada Limited	2006-07-04	Not applicable	Canada
Teva-fentanyl	patch	50 mcg	transdermal	Teva Canada Limited	2006-07-04	Not applicable	Canada
Teva-fentanyl	patch	25 mcg	transdermal	Teva Canada Limited	2006-07-04	Not applicable	Canada
Transmucosal Fentanyl Citrate	lozenge	1200 1/1	oral; transmucosal	H.J. Harkins Company, Inc.	2006-09-06	2016-04-05	US
Transmucosal Fentanyl Citrate	lozenge	400 ug/1	oral; transmucosal	H.J. Harkins Company, Inc.	2006-09-06	2016-04-05	US
Transmucosal Fentanyl Citrate	lozenge	600 ug/1	oral; transmucosal	H.J. Harkins Company, Inc.	2006-09-06	2016-04-05	US

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-fentanyl Matrix	patch	25 mcg	transdermal	Apotex Inc	2009-05-13	Not applicable	Canada
Apo-fentanyl Matrix	patch	100 mcg	transdermal	Apotex Inc	2009-05-13	Not applicable	Canada
Apo-fentanyl Matrix	patch	75 mcg	transdermal	Apotex Inc	2009-05-13	Not applicable	Canada
Apo-fentanyl Matrix	patch	50 mcg	transdermal	Apotex Inc	2009-05-13	Not applicable	Canada
Fentanyl	patch, extended release	7.5 mg/72h	transdermal	Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC	2011-12-09	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Apotex Corp.	2010-03-01	2016-04-05	US
Fentanyl	patch, extended release	10 mg/72h	transdermal	Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC	2011-12-09	2016-04-05	US
Fentanyl	patch, extended release	50 ug/h	transdermal	bryant ranch prepack	2013-04-04	2016-04-05	US
Fentanyl	patch	100 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2005-01-28	Not applicable	US
Fentanyl	patch, extended release	50 ug/h	transdermal	bryant ranch prepack	2010-03-01	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Dispensing Solutions Inc.	2006-11-06	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Teva Pharmaceuticals USA Inc	2008-12-22	2016-03-29	US
Fentanyl	patch, extended release	50 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch, extended release	50 ug/h	transdermal	Actavis Pharma, Inc.	2007-09-01	Not applicable	US
Fentanyl	patch, extended release	75 ug/h	transdermal	bryant ranch prepack	2013-04-04	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Upsher Smith Laboratories, Inc.	2013-03-01	2015-12-31	US
Fentanyl	patch, extended release	5 mg/72h	transdermal	Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC	2011-12-09	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch	1.28 mg/[USP'U]	transdermal	Physicians Total Care, Inc.	2008-11-18	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	bryant ranch prepack	2013-04-04	2016-04-05	US
Fentanyl	patch	75 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2005-01-28	Not applicable	US
Fentanyl	patch, extended release	50 ug/h	transdermal	DIRECT RX	2015-01-01	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Dispensing Solutions Inc.	2006-11-06	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Actavis Pharma, Inc.	2007-09-01	Not applicable	US
Fentanyl	patch, extended release	2.5 mg/72h	transdermal	Lake Erie Medical & Surgical Supply DBA Quality Care Products LLC	2011-12-09	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch	10.2 mg/[USP'U]	transdermal	Physicians Total Care, Inc.	2005-07-14	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	bryant ranch prepack	2010-03-01	2016-04-05	US
Fentanyl	patch	50 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2005-01-28	Not applicable	US
Fentanyl	patch, extended release	25 ug/h	transdermal	DIRECT RX	2015-01-01	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Dispensing Solutions Inc.	2006-11-06	2016-04-05	US
Fentanyl	patch, extended release	50 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch	7.65 mg/[USP'U]	transdermal	Physicians Total Care, Inc.	2005-07-14	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	bryant ranch prepack	2010-03-01	2016-04-05	US
Fentanyl	patch	25 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2005-01-28	Not applicable	US
Fentanyl	patch	100 ug/h	transdermal	St. Marys Medical Park Pharmacy	2011-01-26	2016-04-05	US
Fentanyl	patch	100 ug/h	transdermal	DAVA Pharmaceuticals, Inc.	2010-11-01	2016-04-05	US
Fentanyl	patch	100 ug/h	transdermal	Par Pharmaceutical Inc.	2007-08-20	2016-04-05	US
Fentanyl	patch	12 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2007-01-24	Not applicable	US
Fentanyl	patch	50 ug/h	transdermal	St. Marys Medical Park Pharmacy	2011-01-26	2016-04-05	US
Fentanyl	patch	75 ug/h	transdermal	DAVA Pharmaceuticals, Inc.	2010-11-01	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	bryant ranch prepack	2007-09-01	2016-04-05	US
Fentanyl	patch, extended release	12 ug/h	transdermal	Apotex Corp.	2016-01-22	2016-04-05	US
Fentanyl	patch	100 ug/h	transdermal	Lake Erie Medical DBA Quality Care Products LLC	2013-01-09	2016-04-05	US
Fentanyl	patch	75 ug/h	transdermal	Par Pharmaceutical Inc.	2007-08-20	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch	5.1 mg/[USP'U]	transdermal	Physicians Total Care, Inc.	2005-07-14	2016-04-05	US
Fentanyl	patch	87.5 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2015-02-24	Not applicable	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Teva Pharmaceuticals USA Inc	2008-10-20	2016-03-29	US
Fentanyl	patch	25 ug/h	transdermal	St. Marys Medical Park Pharmacy	2011-01-26	2016-04-05	US
Fentanyl	patch	50 ug/h	transdermal	DAVA Pharmaceuticals, Inc.	2010-11-01	2016-04-05	US
Fentanyl	patch, extended release	50 ug/h	transdermal	bryant ranch prepack	2007-09-01	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Upsher Smith Laboratories, Inc.	2013-03-01	2015-12-31	US
Fentanyl	patch	12 ug/h	transdermal	Lake Erie Medical DBA Quality Care Products LLC	2013-01-09	2016-04-05	US
Fentanyl	patch	50 ug/h	transdermal	Par Pharmaceutical Inc.	2007-08-20	2016-04-05	US
Fentanyl	patch, extended release	5 mg/72h	transdermal	STAT Rx USA LLC	2007-08-20	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Apotex Corp.	2010-03-01	2016-04-05	US
Fentanyl	patch	2.55 mg/[USP'U]	transdermal	Physicians Total Care, Inc.	2005-07-14	2016-04-05	US
Fentanyl	patch	62.5 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2015-02-24	Not applicable	US
Fentanyl	patch, extended release	25 ug/h	transdermal	bryant ranch prepack	2010-03-01	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Teva Pharmaceuticals USA Inc	2008-10-20	2016-03-29	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch	25 ug/h	transdermal	DAVA Pharmaceuticals, Inc.	2010-11-01	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	Actavis Pharma, Inc.	2007-09-01	Not applicable	US
Fentanyl	patch, extended release	25 ug/h	transdermal	bryant ranch prepack	2007-09-01	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Upsher Smith Laboratories, Inc.	2013-03-01	2015-12-31	US
Fentanyl	patch	25 ug/h	transdermal	Par Pharmaceutical Inc.	2007-08-20	2016-04-05	US
Fentanyl	patch, extended release	2.5 mg/72h	transdermal	STAT Rx USA LLC	2007-08-20	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Apotex Corp.	2010-03-01	2016-04-05	US
Fentanyl	patch, extended release	100 ug/h	transdermal	H.J. Harkins Company, Inc.	2010-03-01	2016-04-05	US
Fentanyl	patch, extended release	50 ug/h	transdermal	Upsher Smith Laboratories, Inc.	2013-03-01	2015-12-31	US
Fentanyl	patch, extended release	50 ug/h	transdermal	Apotex Corp.	2010-03-01	2016-04-05	US
Fentanyl	patch, extended release	25 ug/h	transdermal	H.J. Harkins Company, Inc.	2010-03-01	2016-04-05	US
Fentanyl	patch	37.5 ug/h	transdermal	Mylan Pharmaceuticals Inc.	2015-02-24	Not applicable	US
Fentanyl	patch, extended release	50 ug/h	transdermal	Teva Pharmaceuticals USA Inc	2008-12-22	2016-03-29	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Apotex Corp.	2013-04-04	2016-04-05	US
Fentanyl	patch	50 ug/h	transdermal	Corium International, Inc.	2007-08-20	2016-04-05	US
Fentanyl	patch, extended release	75 ug/h	transdermal	Actavis Pharma, Inc.	2007-09-01	Not applicable	US
Fentanyl	patch, extended release	100 ug/h	transdermal	bryant ranch prepack	2007-09-01	2016-04-05	US
Fentanyl - Novaplus	patch, extended release	50 ug/h	transdermal	Watson Laboratories, Inc.	2007-09-01	Not applicable	US
Fentanyl - Novaplus	patch, extended release	25 ug/h	transdermal	Watson Laboratories, Inc.	2007-09-01	Not applicable	US
Fentanyl - Novaplus	patch, extended release	100 ug/h	transdermal	Watson Laboratories, Inc.	2007-09-01	Not applicable	US
Fentanyl - Novaplus	patch, extended release	75 ug/h	transdermal	Watson Laboratories, Inc.	2007-09-01	Not applicable	US
Fentanyl Buccal	tablet	800 ug/1	buccal; oral; transmucosal	Watson Laboratories, Inc.	2011-01-07	Not applicable	US
Fentanyl Buccal	tablet	600 ug/1	buccal; oral; transmucosal	Watson Laboratories, Inc.	2011-01-07	Not applicable	US
Fentanyl Buccal	tablet	400 ug/1	buccal; oral; transmucosal	Watson Laboratories, Inc.	2011-01-07	Not applicable	US
Fentanyl Buccal	tablet	200 ug/1	buccal; oral; transmucosal	Watson Laboratories, Inc.	2011-01-07	Not applicable	US
Fentanyl Buccal	tablet	100 ug/1	buccal; oral; transmucosal	Watson Laboratories, Inc.	2011-01-07	Not applicable	US
Fentanyl Citrate	injection	50 ug/mL	intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	1200 ug/1	oral; transmucosal	Par Pharmaceutical Inc.	2011-10-17	2016-04-05	US
Fentanyl Citrate	lozenge	800 ug/1	oral; transmucosal	Lake Erie Medical DBA Quality Care Products LLC	2011-10-17	2016-04-05	US
Fentanyl Citrate	lozenge	200 ug/1	transmucosal	Mallinckrodt Inc.	2010-01-15	Not applicable	US
Fentanyl Citrate	injection	50 ug/mL	intramuscular; intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	800 ug/1	oral; transmucosal	Par Pharmaceutical Inc.	2011-10-17	2016-04-05	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Baxter Healthcare Corporation	2010-06-25	2015-12-29	US
Fentanyl Citrate	injection	50 ug/mL	intramuscular; intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	600 ug/1	oral; transmucosal	Par Pharmaceutical Inc.	2011-10-17	2016-04-05	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Hospira, Inc.	1991-09-24	Not applicable	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Baxter Healthcare Corporation	2010-06-25	2015-12-29	US
Fentanyl Citrate	lozenge	1600 ug/1	transmucosal	Mallinckrodt Inc.	2010-01-15	Not applicable	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Baxter Healthcare Corporation	2010-06-25	2015-12-29	US
Fentanyl Citrate	injection	50 ug/mL	intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	400 ug/1	oral; transmucosal	Par Pharmaceutical Inc.	2011-10-17	2016-04-05	US
Fentanyl Citrate	lozenge	1200 ug/1	transmucosal	Mallinckrodt Inc.	2010-01-15	Not applicable	US
Fentanyl Citrate	injection, solution	50 ug/mL	intramuscular; intravenous	Baxter Healthcare Corporation	2010-06-25	2015-12-29	US
Fentanyl Citrate	injection	50 ug/mL	intramuscular; intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	200 ug/1	oral; transmucosal	Par Pharmaceutical Inc.	2011-10-17	2016-04-05	US
Fentanyl Citrate	lozenge	800 ug/1	transmucosal	Mallinckrodt Inc.	2010-01-15	Not applicable	US
Fentanyl Citrate	injection	50 ug/mL	intramuscular; intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	600 ug/1	transmucosal	Mallinckrodt Inc.	2010-01-15	Not applicable	US
Fentanyl Citrate	lozenge	400 ug/1	transmucosal	Mallinckrodt Inc.	2010-01-15	Not applicable	US
Fentanyl Citrate	injection	50 ug/mL	intravenous	West Ward Pharmaceutical Corp.	1984-07-11	Not applicable	US
Fentanyl Citrate	lozenge	1600 ug/1	oral; transmucosal	Par Pharmaceutical Inc.	2011-10-17	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	100 ug/h	transdermal	Lake Erie Medical DBA Quality Care Products LLC	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	75 ug/h	transdermal	Mallinckrodt, Inc.	2011-06-06	Not applicable	US
Fentanyl Transdermal System	patch, extended release	100 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	75 ug/h	transdermal	Lake Erie Medical DBA Quality Care Products LLC	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	50 ug/h	transdermal	Mallinckrodt, Inc.	2011-06-06	Not applicable	US
Fentanyl Transdermal System	patch, extended release	25 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	50 ug/h	transdermal	Lake Erie Medical DBA Quality Care Products LLC	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	25 ug/h	transdermal	Mallinckrodt, Inc.	2011-06-06	Not applicable	US
Fentanyl Transdermal System	patch, extended release	75 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	12.5 ug/h	transdermal	Mallinckrodt, Inc.	2011-06-06	Not applicable	US
Fentanyl Transdermal System	patch, extended release	50 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	25 ug/h	transdermal	Lake Erie Medical DBA Quality Care Products LLC	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	100 ug/h	transdermal	Mallinckrodt, Inc.	2011-06-06	Not applicable	US
Fentanyl Transdermal System	patch, extended release	75 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	50 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	25 ug/h	transdermal	Rebel Distributors Corp	2011-02-09	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	50 ug/h	transdermal	Rebel Distributors Corp.	2011-02-09	2016-04-05	US
Fentanyl Transdermal System	patch, extended release	100 ug/h	transdermal	bryant ranch prepack	2011-06-06	2016-04-05	US

Over the Counter Products

Not Available

International Brands

Name	Company
Durogesic	Janssen
Fentanest	Pfizer
Nasalfent	Archimedes
Rapinyl	Gedeon Richter

Brand mixtures

Name	Labeller	Ingredients
Fentanyl Citrate, Bupivacaine HCl	Cantrell Drug Company	Bupivacaine Fentanyl
Innovar Inj	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	Droperidol Fentanyl

Salts

Name/CAS	Structure	Properties
Fentanyl citrate 990-73-8		InChI Key: IVLVTNPOHDFFCJ-UHFFFAOYSA-N Monoisotopic Mass: 528.247166138 Average Mass: 528.594	DBSALT000301
Fentanyl hydrochloride		Not applicable	DBSALT001226

Categories

UNII

UF599785JZ

CAS number

437-38-7

Weight

Average: 336.4705
Monoisotopic: 336.220163528

Chemical Formula

C₂₂H₂₈N₂O

InChI Key

InChIKey=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

Description

This 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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Fentanyls

Direct Parent

Fentanyls

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:119915 )
monocarboxylic acid amide (CHEBI:119915 )
anilide (CHEBI:119915 )

Pharmacology

Indication

For the treatment of cancer patients with severe pain that breaks through their regular narcotic therapy.

Pharmacodynamics

Fentanyl is an opioid analgesic. Fentanyl interacts predominately with the opioid mu-receptor but also binds to kappa and delta-type opioid receptors. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, Fentanyl exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Fentanyl may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Fentanyl depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.

Mechanism of action

Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Fentanyl's analgesic activity is, most likely, due to its conversion to morphine. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hypopolarization and reduced neuronal excitability.

Absorption

Bioavailability 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 binding

80-85%

Metabolism

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

Substrate	Enzymes	Product
Fentanyl	Cytochrome P450 3A4	norfentanyl	Details

Route of elimination

Fentanyl is metabolized primarily via human cytochrome P450 3A4 isoenzyme system and mostly eliminated in urine. Within 72 hours of IV fentanyl administration, approximately 75% of the dose is excreted in urine, mostly as metabolites with less than 10% representing unchanged drug.

Half life

7 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]

Toxicity

Fentanyl has an LD50 of 3.1 milligrams per kilogram in rats, and, 0.03 milligrams per kilogram in monkeys. The LD50 in humans is not known.

Affected organisms

Humans and other mammals

Pathways

Pathway	Category	SMPDB ID
Fentanyl Action Pathway	Drug action	SMP00415

SNP Mediated Effects

Not Available

SNP Mediated Adverse Drug Reactions

Not Available

ADMET

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9766
Blood Brain Barrier	+	0.9901
Caco-2 permeable	+	0.6459
P-glycoprotein substrate	Substrate	0.6082
P-glycoprotein inhibitor I	Inhibitor	0.7161
P-glycoprotein inhibitor II	Non-inhibitor	0.8371
Renal organic cation transporter	Inhibitor	0.5824
CYP450 2C9 substrate	Non-substrate	0.7879
CYP450 2D6 substrate	Non-substrate	0.9117
CYP450 3A4 substrate	Substrate	0.5856
CYP450 1A2 substrate	Non-inhibitor	0.7715
CYP450 2C9 inhibitor	Non-inhibitor	0.873
CYP450 2D6 inhibitor	Non-inhibitor	0.6327
CYP450 2C19 inhibitor	Non-inhibitor	0.5724
CYP450 3A4 inhibitor	Non-inhibitor	0.8218
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.7346
Ames test	Non AMES toxic	0.8417
Carcinogenicity	Non-carcinogens	0.8536
Biodegradation	Not ready biodegradable	0.8554
Rat acute toxicity	3.9836 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.796
hERG inhibition (predictor II)	Inhibitor	0.6791

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

4uOrtho LLC
Actavis Group
Akorn Inc.
Alza Corp.
Anesta Corp.
Apotex Inc.
Aveva Drug Delivery Systems Inc.
B&B Pharmaceuticals
Barr Pharmaceuticals
Baxter International Inc.
Cephalon Inc.
Chattem Chemicals Inc.
Cima Laboratories Inc.
Corium International Inc.
DAVA Pharmaceuticals
Dispensing Solutions
Hospira Inc.
Janssen-Ortho Inc.
LTS Lohmann Therapy Systems Corp.
Mallinckrodt Inc.
Meda AB
Medisca Inc.
Mylan
Nucare Pharmaceuticals Inc.
Ortho Mcneil Janssen Pharmaceutical Inc.
Pharmakon
Pharmedium
Physicians Total Care Inc.
Quality Care
Sandoz
Stat Rx Usa
Taylor Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
Watson Pharmaceuticals

Dosage forms

Form	Route	Strength
Tablet	sublingual	100 ug/1
Tablet	sublingual	100 mcg
Tablet	sublingual	200 ug/1
Tablet	sublingual	200 mcg
Tablet	sublingual	300 ug/1
Tablet	sublingual	300 mcg
Tablet	sublingual	400 mcg
Tablet	sublingual	400 ug/1
Tablet	sublingual	600 ug/1
Tablet	sublingual	600 mcg
Tablet	sublingual	800 ug/1
Tablet	sublingual	800 mcg
Patch	transdermal	100 mcg
Patch	transdermal	12.0 mcg
Patch	transdermal	25 mcg
Patch	transdermal	50 mcg
Patch	transdermal	75 mcg
Patch	transdermal	1.28 mg/[USP'U]
Patch	transdermal	10.2 mg/[USP'U]
Patch	transdermal	100 ug/h
Patch	transdermal	12 ug/h
Patch	transdermal	12 ug/1
Patch	transdermal	12.5 ug/h
Patch	transdermal	2.55 mg/[USP'U]
Patch	transdermal	25 ug/h
Patch	transdermal	37.5 ug/h
Patch	transdermal	5.1 mg/[USP'U]
Patch	transdermal	50 ug/h
Patch	transdermal	62.5 ug/h
Patch	transdermal	7.65 mg/[USP'U]
Patch	transdermal	75 ug/h
Patch	transdermal	87.5 ug/h
Patch, extended release	transdermal	10 mg/72h
Patch, extended release	transdermal	100 ug/h
Patch, extended release	transdermal	12 ug/h
Patch, extended release	transdermal	2.5 mg/72h
Patch, extended release	transdermal	25 ug/h
Patch, extended release	transdermal	5 mg/72h
Patch, extended release	transdermal	50 ug/h
Patch, extended release	transdermal	7.5 mg/72h
Patch, extended release	transdermal	75 ug/h
Tablet	buccal; oral; transmucosal	100 ug/1
Tablet	buccal; oral; transmucosal	200 ug/1
Tablet	buccal; oral; transmucosal	400 ug/1
Tablet	buccal; oral; transmucosal	600 ug/1
Tablet	buccal; oral; transmucosal	800 ug/1
Injection	intramuscular; intravenous	50 ug/mL
Injection	intravenous	50 ug/mL
Injection, solution	intramuscular; intravenous	50 ug/mL
Injection, solution	intravenous	10 ug/mL
Injection, solution	intravenous	20 ug/mL
Injection, solution	intravenous	25 ug/mL
Injection, solution	intravenous	5 ug/mL
Injection, solution	intravenous	50 ug/mL
Lozenge	oral; transmucosal	1200 ug/1
Lozenge	oral; transmucosal	1600 ug/1
Lozenge	oral; transmucosal	200 ug/1
Lozenge	oral; transmucosal	400 ug/1
Lozenge	oral; transmucosal	600 ug/1
Lozenge	oral; transmucosal	800 ug/1
Lozenge	transmucosal	1200 ug/1
Lozenge	transmucosal	1600 ug/1
Lozenge	transmucosal	200 ug/1
Lozenge	transmucosal	400 ug/1
Lozenge	transmucosal	600 ug/1
Lozenge	transmucosal	800 ug/1
Solution	intramuscular; intravenous; epidural	50 mcg
Liquid	intramuscular; intravenous; epidural	50 mcg
Injection, solution	epidural
Patch, extended release	transdermal	12.5 ug/h
Patch (extended release)	transdermal	100 mcg
Patch (extended release)	transdermal	25 mcg
Patch (extended release)	transdermal	50 mcg
Patch (extended release)	transdermal	75 mcg
Tablet (effervescent)	buccal; sublingual	100 mcg
Tablet (effervescent)	buccal; sublingual	200 mcg
Tablet (effervescent)	buccal; sublingual	400 mcg
Tablet (effervescent)	buccal; sublingual	600 mcg
Tablet (effervescent)	buccal; sublingual	800 mcg
Liquid	intramuscular; intravenous
Solution	nasal	100 mcg
Solution	nasal	200 mcg
Solution	nasal	50 mcg
Patch	transdermal	40 ug/1
Spray	nasal	100 ug/1
Spray	nasal	300 ug/1
Spray	nasal	400 ug/1
Film, soluble	buccal	1200 mcg
Film, soluble	buccal	200 mcg
Film, soluble	buccal	400 mcg
Film, soluble	buccal	600 mcg
Film, soluble	buccal	800 mcg
Patch	transdermal	10 mg
Patch	transdermal	2.5 mg
Patch	transdermal	5 mg
Patch	transdermal	7.5 mg
Patch	transdermal	37 mcg
Spray	sublingual	.1 mg/1
Spray	sublingual	.2 mg/1
Spray	sublingual	.4 mg/1
Spray	sublingual	.6 mg/1
Spray	sublingual	.8 mg/1
Patch	transdermal	12 mcg
Lozenge	oral; transmucosal	1200 1/1

Prices

Unit description	Cost	Unit
Fentanyl base powder	1498.18USD	g
Fentanyl citrate powder	1062.5USD	g
Duragesic-100 5 100 mcg/hr Patches Box	411.59USD	box
Duragesic-75 5 75 mcg/hr Patches Box	318.93USD	box
Fentanyl 5 100 mcg/hr Patches Box	210.0USD	box
Duragesic-50 5 50 mcg/hr Patches Box	205.78USD	box
Actiq 1600 mcg lozenge	150.29USD	lozenge
Fentanyl 5 50 mcg/hr Patches Box	129.99USD	box
Actiq 1200 mcg lozenge	121.82USD	lozenge
Actiq 1600 mcg Lollipop	119.42USD	lollipop
Duragesic-25 5 25 mcg/hr Patches Box	114.42USD	box
Duragesic-12 5 12 mcg/hr Patches Box	95.99USD	box
Actiq 800 mcg lozenge	93.76USD	lozenge
Actiq 1200 mcg Lollipop	85.7USD	lollipop
Duragesic 100 mcg/hr patch	81.36USD	patch
Actiq 600 mcg lozenge	79.16USD	lozenge
Actiq 800 mcg Lollipop	75.98USD	lollipop
Fentanyl 5 12 (12.5)mcg/hr Patches Box	67.99USD	box
Fentanyl 5 25 mcg/hr Patches Box	66.66USD	box
Actiq 600 mcg Lollipop	65.13USD	lollipop
Actiq 400 mcg lozenge	64.62USD	lozenge
Fentanyl 100 mcg/hr patch	61.69USD	patch
Duragesic 75 mcg/hr patch	61.3USD	patch
Fentora 800 mcg buccal tablet	54.77USD	tablet
Actiq 400 mcg Lollipop	53.75USD	lollipop
Actiq 200 mcg lozenge	51.05USD	lozenge
Fentora 600 mcg buccal tablet	47.37USD	tablet
Fentanyl 75 mcg/hr patch	46.48USD	patch
Actiq 200 mcg Lollipop	42.14USD	lollipop
Duragesic 50 mcg/hr patch	40.19USD	patch
FentaNYL Citrate 1600 mcg Lollipop	38.53USD	lollipop
Fentora 400 mcg buccal tablet	34.24USD	tablet
Fentanyl 50 mcg/hr patch	30.47USD	patch
FentaNYL Citrate 1200 mcg Lollipop	30.0USD	lollipop
Fentora 300 mcg buccal tablet	28.84USD	tablet
Fentora 200 mcg buccal tablet	23.57USD	tablet
Duragesic 25 mcg/hr patch	21.98USD	patch
FentaNYL Citrate 400 mcg Lollipop	20.0USD	lollipop
Fentora 100 mcg buccal tablet	18.64USD	tablet
Duragesic 12 mcg/hr patch	18.21USD	patch
Fentanyl 25 mcg/hr patch	16.67USD	patch
Fentanyl 12 mcg/hr patch	13.8USD	patch
Fentanyl 0.05 mg/ml vial	1.96USD	ml
Fentanyl cit 1500 mcg/30 ml	1.44USD	ml
Fentanyl-ns 50 mcg/ml syringe	1.0USD	ml
Fentanyl-ns 300 mcg/30 ml syr	0.99USD	ml
Fentanyl-ns 20 mcg/ml syringe	0.72USD	ml
Fentanyl-ns 10 mcg/ml syringe	0.64USD	ml
Fentanyl cit 2750 mcg/55 ml	0.35USD	ml
Fentanyl-ns 500 mcg/50 ml syr	0.31USD	ml
Sublimaze 0.05 mg/ml ampul	0.23USD	ml
Fentanyl 0.05 mg/ml ampul	0.21USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US5697896	No	1996-12-16	2016-12-16	US
US5843014	No	1995-12-01	2015-12-01	US
US6159498	No	1996-10-18	2016-10-18	US
US6169920	No	1998-01-02	2018-01-02	US
US6181963	No	1999-11-02	2019-11-02	US
US6195582	No	1999-01-28	2019-01-28	US
US6200604	No	1999-03-26	2019-03-26	US
US6317629	No	1995-06-02	2012-06-02	US
US6432440	No	1998-04-20	2018-04-20	US
US6759059	No	1999-09-24	2019-09-24	US
US6761910	No	1999-09-24	2019-09-24	US
US6881208	No	2002-04-19	2022-04-19	US
US6974590	No	1999-03-26	2019-03-26	US
US6975902	No	2004-04-01	2024-04-01	US
US7579019	No	2000-01-22	2020-01-22	US
US7862832	No	2008-06-15	2028-06-15	US
US7862833	No	2008-06-15	2028-06-15	US
US7910132	No	1999-09-24	2019-09-24	US
US8092832	No	2004-12-30	2024-12-30	US
US8119158	No	2004-12-30	2024-12-30	US
US8216604	No	2004-10-03	2024-10-03	US
US8301238	No	2011-09-30	2031-09-30	US
US8428708	No	2012-05-21	2032-05-21	US
US8428709	No	2012-06-11	2032-06-11	US
US8486972	No	2010-04-27	2030-04-27	US
US8486973	No	2010-04-27	2030-04-27	US
US8728441	No	1999-03-26	2019-03-26	US
US8753611	No	1999-03-26	2019-03-26	US
US8765100	No	1999-03-26	2019-03-26	US
US8781571	No	2012-03-31	2032-03-31	US
US8835459	No	2007-01-25	2027-01-25	US
US8835460	No	2007-01-25	2027-01-25	US
US8889176	No	2004-01-16	2024-01-16	US
US9078814	No	2004-01-08	2024-01-08	US
US9095706	No	2013-02-03	2033-02-03	US
US9241935	No	2007-01-25	2027-01-25	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point	83-84	US. Patent 3,141,823.
water solubility	200 mg/L (at 25 °C)	ROY,SD & FLYNN,GL (1988)
logP	4.05	SANGSTER (1993)

Predicted Properties

Property	Value	Source
Water Solubility	0.024 mg/mL	ALOGPS
logP	4.12	ALOGPS
logP	3.82	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	8.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	23.55 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	103.48 m³·mol^-1	ChemAxon
Polarizability	40.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
MS	Mass Spectrum (Electron Ionization)	splash10-zyj0000000-7ce3a6f35f5dee98185f	View in MoNA

References

Synthesis Reference

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

US20060100438

General References

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 ]
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 ]
Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. [PubMed:18001263 ]
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

Resource	Link
KEGG Drug	D00320
PubChem Compound	3345
PubChem Substance	46506372
ChemSpider	3228
BindingDB	50008984
ChEBI	119915
ChEMBL	CHEMBL596
Therapeutic Targets Database	DAP000072
PharmGKB	PA449599
IUPHAR	1626
Guide to Pharmacology	1626
Drug Product Database	10075
RxList	http://www.rxlist.com/cgi/generic2/fentanyl.htm
Drugs.com	http://www.drugs.com/fentanyl.html
Wikipedia	Fentanyl

ATC Codes

N01AH01

N01AH51

N02AB03

AHFS Codes

28:08.08

PDB Entries

Not Available

FDA label

Download (507 KB)

MSDS

Download (75.5 KB)

Interactions

Drug Interactions

Drug
Acepromazine	Acepromazine may increase the hypotensive activities of Fentanyl.
Acetazolamide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Acetazolamide.
Acetophenazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Acetophenazine.
Alvimopan	The risk or severity of adverse effects can be increased when Fentanyl is combined with Alvimopan.
Amiloride	The risk or severity of adverse effects can be increased when Fentanyl is combined with Amiloride.
Amisulpride	The risk or severity of adverse effects can be increased when Fentanyl is combined with Amisulpride.
Ammonium chloride	Ammonium chloride may increase the excretion rate of Fentanyl which could result in a higher serum level.
Amphetamine	Amphetamine may increase the analgesic activities of Fentanyl.
Aprepitant	The serum concentration of Fentanyl can be increased when it is combined with Aprepitant.
Aripiprazole	The risk or severity of adverse effects can be increased when Fentanyl is combined with Aripiprazole.
Atazanavir	The serum concentration of Fentanyl can be increased when it is combined with Atazanavir.
Azelastine	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Azelastine.
Baclofen	The risk or severity of adverse effects can be increased when Baclofen is combined with Fentanyl.
Bendroflumethiazide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Bendroflumethiazide.
Benzquinamide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Benzquinamide.
Bepridil	Fentanyl may increase the bradycardic activities of Bepridil.
Bexarotene	The serum concentration of Fentanyl can be decreased when it is combined with Bexarotene.
Boceprevir	The serum concentration of Fentanyl can be increased when it is combined with Boceprevir.
Bosentan	The serum concentration of Fentanyl can be decreased when it is combined with Bosentan.
Brimonidine	Brimonidine may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Bumetanide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Bumetanide.
Butorphanol	Butorphanol may decrease the analgesic activities of Fentanyl.
Carbamazepine	The serum concentration of Fentanyl can be decreased when it is combined with Carbamazepine.
Carphenazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Carphenazine.
Cathinone	Cathinone may increase the analgesic activities of Fentanyl.
Ceritinib	The serum concentration of Fentanyl can be increased when it is combined with Ceritinib.
Chlormezanone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Chlormezanone.
Chlorothiazide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorothiazide.
Chlorpromazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorpromazine.
Chlorprothixene	The risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorprothixene.
Chlorthalidone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorthalidone.
Clarithromycin	The serum concentration of Fentanyl can be increased when it is combined with Clarithromycin.
Clozapine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Clozapine.
Cobicistat	The serum concentration of Fentanyl can be increased when it is combined with Cobicistat.
Conivaptan	The serum concentration of Fentanyl can be increased when it is combined with Conivaptan.
Crizotinib	The serum concentration of Fentanyl can be increased when it is combined with Crizotinib.
Cyclothiazide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Cyclothiazide.
Dabrafenib	The serum concentration of Fentanyl can be decreased when it is combined with Dabrafenib.
Dapoxetine	The risk or severity of adverse effects can be increased when Dapoxetine is combined with Fentanyl.
Darunavir	The serum concentration of Fentanyl can be increased when it is combined with Darunavir.
Dasatinib	The serum concentration of Fentanyl can be increased when it is combined with Dasatinib.
Delavirdine	The serum concentration of Fentanyl can be increased when it is combined with Delavirdine.
Desmopressin	The risk or severity of adverse effects can be increased when Fentanyl is combined with Desmopressin.
Dexamethasone	The serum concentration of Fentanyl can be decreased when it is combined with Dexamethasone.
Diltiazem	The serum concentration of Fentanyl can be increased when it is combined with Diltiazem.
Doxylamine	Doxylamine may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Dronabinol	Dronabinol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Dronedarone	The serum concentration of Fentanyl can be increased when it is combined with Dronedarone.
Droperidol	Droperidol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Efavirenz	The serum concentration of Fentanyl can be decreased when it is combined with Efavirenz.
Eluxadoline	Fentanyl may increase the activities of Eluxadoline.
Enzalutamide	The serum concentration of Fentanyl can be decreased when it is combined with Enzalutamide.
Ephedrine	The serum concentration of Fentanyl can be decreased when it is combined with Ephedrine.
Erythromycin	The serum concentration of Fentanyl can be increased when it is combined with Erythromycin.
Eslicarbazepine acetate	The serum concentration of Fentanyl can be decreased when it is combined with Eslicarbazepine acetate.
Ethacrynic acid	The risk or severity of adverse effects can be increased when Fentanyl is combined with Ethacrynic acid.
Ethanol	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Ethanol.
Ethoxzolamide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Ethoxzolamide.
Etravirine	The serum concentration of Fentanyl can be decreased when it is combined with Etravirine.
Fencamfamine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Fencamfamine.
Fluconazole	The serum concentration of Fentanyl can be increased when it is combined with Fluconazole.
Flupentixol	The risk or severity of adverse effects can be increased when Fentanyl is combined with Flupentixol.
Fluphenazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Fluphenazine.
Fluspirilene	The risk or severity of adverse effects can be increased when Fentanyl is combined with Fluspirilene.
Fluvoxamine	The risk or severity of adverse effects can be increased when Fluvoxamine is combined with Fentanyl.
Fosamprenavir	The serum concentration of Fentanyl can be increased when it is combined with Fosamprenavir.
Fosaprepitant	The serum concentration of Fentanyl can be increased when it is combined with Fosaprepitant.
Fosphenytoin	The serum concentration of Fentanyl can be decreased when it is combined with Fosphenytoin.
Furosemide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Furosemide.
Fusidic Acid	The serum concentration of Fentanyl can be increased when it is combined with Fusidic Acid.
Granisetron	Granisetron may increase the serotonergic activities of Fentanyl.
Haloperidol	The risk or severity of adverse effects can be increased when Fentanyl is combined with Haloperidol.
Hydrochlorothiazide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Hydrochlorothiazide.
Hydrocodone	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Hydrocodone.
Hydroflumethiazide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Hydroflumethiazide.
Hydroxyzine	Hydroxyzine may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Idelalisib	The serum concentration of Fentanyl can be increased when it is combined with Idelalisib.
Imatinib	The serum concentration of Fentanyl can be increased when it is combined with Imatinib.
Indapamide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Indapamide.
Indinavir	The serum concentration of Fentanyl can be increased when it is combined with Indinavir.
Ioflupane I 123	Fentanyl may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
Isavuconazonium	The serum concentration of Fentanyl can be increased when it is combined with Isavuconazonium.
Itraconazole	The serum concentration of Fentanyl can be increased when it is combined with Itraconazole.
Ivacaftor	The serum concentration of Fentanyl can be increased when it is combined with Ivacaftor.
Ketoconazole	The serum concentration of Fentanyl can be increased when it is combined with Ketoconazole.
Lorazepam	The risk or severity of adverse effects can be increased when Lorazepam is combined with Fentanyl.
Loxapine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Loxapine.
Luliconazole	The serum concentration of Fentanyl can be increased when it is combined with Luliconazole.
Magnesium Sulfate	Magnesium Sulfate may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Mesoridazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Mesoridazine.
Methotrimeprazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Methotrimeprazine.
Metoclopramide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Metoclopramide.
Metolazone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Metolazone.
Metyrosine	Fentanyl may increase the sedative activities of Metyrosine.
Mifepristone	The serum concentration of Fentanyl can be increased when it is combined with Mifepristone.
Minocycline	Minocycline may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Mitotane	The serum concentration of Fentanyl can be decreased when it is combined with Mitotane.
Modafinil	The serum concentration of Fentanyl can be decreased when it is combined with Modafinil.
Molindone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Molindone.
Nabilone	Nabilone may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Nadolol	Fentanyl may increase the bradycardic activities of Nadolol.
Nafcillin	The serum concentration of Fentanyl can be decreased when it is combined with Nafcillin.
Naltrexone	The therapeutic efficacy of Fentanyl can be decreased when used in combination with Naltrexone.
Naphazoline	The serum concentration of Fentanyl can be decreased when it is combined with Naphazoline.
Nefazodone	The serum concentration of Fentanyl can be increased when it is combined with Nefazodone.
Nelfinavir	The serum concentration of Fentanyl can be increased when it is combined with Nelfinavir.
Nilotinib	The serum concentration of Fentanyl can be increased when it is combined with Nilotinib.
Olanzapine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Olanzapine.
Ondansetron	The risk or severity of adverse effects can be increased when Fentanyl is combined with Ondansetron.
Orphenadrine	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Orphenadrine.
Oxymetazoline	The serum concentration of Fentanyl can be decreased when it is combined with Oxymetazoline.
Palbociclib	The serum concentration of Fentanyl can be increased when it is combined with Palbociclib.
Paliperidone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Paliperidone.
Paraldehyde	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Paraldehyde.
Pegvisomant	The therapeutic efficacy of Pegvisomant can be decreased when used in combination with Fentanyl.
Perampanel	Perampanel may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Perphenazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Perphenazine.
Phenelzine	Fentanyl may increase the serotonergic activities of Phenelzine.
Phenobarbital	The serum concentration of Fentanyl can be decreased when it is combined with Phenobarbital.
Phenylephrine	The serum concentration of Fentanyl can be decreased when it is combined with Phenylephrine.
Phenytoin	The serum concentration of Fentanyl can be decreased when it is combined with Phenytoin.
Pimozide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Pimozide.
Piperacetazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Piperacetazine.
Posaconazole	The serum concentration of Fentanyl can be increased when it is combined with Posaconazole.
Pramipexole	Fentanyl may increase the sedative activities of Pramipexole.
Primidone	The serum concentration of Fentanyl can be decreased when it is combined with Primidone.
Prochlorperazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Prochlorperazine.
Procyclidine	The risk or severity of adverse effects can be increased when Procyclidine is combined with Fentanyl.
Promazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Promazine.
Propylhexedrine	The serum concentration of Fentanyl can be decreased when it is combined with Propylhexedrine.
Pseudoephedrine	The serum concentration of Fentanyl can be decreased when it is combined with Pseudoephedrine.
Quetiapine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Quetiapine.
Ramosetron	Fentanyl may increase the activities of Ramosetron.
Remoxipride	The risk or severity of adverse effects can be increased when Fentanyl is combined with Remoxipride.
Reserpine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Reserpine.
Rifabutin	The serum concentration of Fentanyl can be decreased when it is combined with Rifabutin.
Rifampicin	The serum concentration of Fentanyl can be decreased when it is combined with Rifampicin.
Rifapentine	The serum concentration of Fentanyl can be decreased when it is combined with Rifapentine.
Risperidone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Risperidone.
Ritonavir	The serum concentration of Fentanyl can be increased when it is combined with Ritonavir.
Ropinirole	Fentanyl may increase the sedative activities of Ropinirole.
Rotigotine	Fentanyl may increase the sedative activities of Rotigotine.
Rufinamide	The risk or severity of adverse effects can be increased when Rufinamide is combined with Fentanyl.
Saquinavir	The serum concentration of Fentanyl can be increased when it is combined with Saquinavir.
Sertindole	The risk or severity of adverse effects can be increased when Fentanyl is combined with Sertindole.
Simeprevir	The serum concentration of Fentanyl can be increased when it is combined with Simeprevir.
Sodium oxybate	Sodium oxybate may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Spironolactone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Spironolactone.
St. John's Wort	The serum concentration of Fentanyl can be decreased when it is combined with St. John's Wort.
Stiripentol	The serum concentration of Fentanyl can be increased when it is combined with Stiripentol.
Succinylcholine	Succinylcholine may increase the bradycardic activities of Fentanyl.
Sulpiride	The risk or severity of adverse effects can be increased when Fentanyl is combined with Sulpiride.
Suvorexant	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Suvorexant.
Tapentadol	Tapentadol may increase the central nervous system depressant (CNS depressant) activities of Fentanyl.
Telaprevir	The serum concentration of Fentanyl can be increased when it is combined with Telaprevir.
Telithromycin	The serum concentration of Fentanyl can be increased when it is combined with Telithromycin.
Thalidomide	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Thalidomide.
Thioridazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Thioridazine.
Thiothixene	The risk or severity of adverse effects can be increased when Fentanyl is combined with Thiothixene.
Ticrynafen	The risk or severity of adverse effects can be increased when Fentanyl is combined with Ticrynafen.
Torasemide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Torasemide.
Tramadol	The risk or severity of adverse effects can be increased when Tramadol is combined with Fentanyl.
Tranylcypromine	Fentanyl may increase the serotonergic activities of Tranylcypromine.
Triamterene	The risk or severity of adverse effects can be increased when Fentanyl is combined with Triamterene.
Trichlormethiazide	The risk or severity of adverse effects can be increased when Fentanyl is combined with Trichlormethiazide.
Trifluoperazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Trifluoperazine.
Triflupromazine	The risk or severity of adverse effects can be increased when Fentanyl is combined with Triflupromazine.
Triprolidine	The serum concentration of Fentanyl can be decreased when it is combined with Triprolidine.
Verapamil	The serum concentration of Fentanyl can be increased when it is combined with Verapamil.
Voriconazole	The serum concentration of Fentanyl can be increased when it is combined with Voriconazole.
Ziprasidone	The risk or severity of adverse effects can be increased when Fentanyl is combined with Ziprasidone.
Zolpidem	Fentanyl may increase the central nervous system depressant (CNS depressant) activities of Zolpidem.
Zuclopenthixol	The risk or severity of adverse effects can be increased when Fentanyl is combined with Zuclopenthixol.

Food Interactions

Avoid alcohol.

Targets

Details

1. Mu-type opioid receptor

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

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 ]
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 ]
Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [PubMed:16332149 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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 ]

Details

2. Delta-type opioid receptor

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

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Details

3. Kappa-type opioid receptor

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

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

Details

1. Cytochrome P450 3A4

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

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 ]
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 ]
Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details

2. Cytochrome P450 3A5

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

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 ]
Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details

3. Cytochrome P450 3A7

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

Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Details

1. Multidrug resistance protein 1

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

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 ]

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Drug created on June 13, 2005 07:24 / Updated on April 20, 2016 02:08

Structure for DB00813 (Fentanyl)

Targets

References

References

References

Enzymes

References

References

References

Transporters

References