Identification

Name
Fentanyl
Accession Number
DB00813
Description

Fentanyl, a potent opioid agonist, was developed in the 1950s to fill a need for strong and rapid analgesia.8 Because of these characteristics, fentanyl is commonly used to treat chronic cancer pain or in anesthesia.Label,15,16,17,18,19,20,21 Fentanyl is related to other opioids like morphine and oxycodone.

Fentanyl's high potency has also made it a common adulterant in illicit drugs, especially heroin.8 In 2017, 47600 overdose deaths in the United States involved some opioid (over 2/3 of all overdose deaths).22 Opioid overdoses kill an average of 11 Canadians daily.23

Fentanyl was FDA approved in 1968.Label,15,16,17,18,19,20,21

Type
Small Molecule
Groups
Approved, Illicit, Investigational, Vet approved
Structure
Thumb
Weight
Average: 336.4705
Monoisotopic: 336.220163528
Chemical Formula
C22H28N2O
Synonyms
  • 1-Phenethyl-4-(N-phenylpropionamido)piperidine
  • 1-phenethyl-4-N-propionylanilinopiperidine
  • Fentanil
  • Fentanila
  • Fentanilo
  • Fentanyl
  • Fentanyl CII
  • Fentanylum
  • N-(1-phenethyl-4-piperidinyl)-N-phenylpropionamide
  • N-(1-phenethyl-4-piperidyl)propionanilide
  • N-(1-Phenethyl-piperidin-4-yl)-N-phenyl-propionamide
  • N-(1-phenethylpiperidin-4-yl)-N-phenylpropionamide
  • N-phenethyl-4-(N-propionylanilino)piperidine
  • N-phenyl-N-(1-(2-phenylethyl)-4-piperidinyl)propanamide
  • Phentanyl
External IDs
  • AD 923
  • AD-923
  • IDS-NF-001
  • McN-JR 4263-49
  • R 4263
  • R 5240

Pharmacology

Indication

Fentanyl intravenous or intramuscular injections are indicated for short term analgesia during induction, maintenance, and recovery from general or regional anesthesia.Label These injections are also used with a neuroleptic for premedication, induction, and as an adjunct to maintenance of anesthesia.Label Finally, fentanyl intravenous or intramuscular injections are used with oxygen for anesthesia in high risk patients.Label

Fentanyl sublingual tablets, transmucosal lozenges, buccal tablets, sublingual sprays, transdermal systems, and nasal sprays are indicated for the management of breakthrough pain in opioid tolerant cancer patients who require around the clock pain management.15,16,17,18,19,20

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Fentanyl produces strong analgesia through its activation of opioid receptors.Label,6 It has a duration of action of several hours and a wider therapeutic index as patients develop tolerance to opioids.Label Fentanyl is associated with a risk of addiction and abuse and should not be mixed with alcohol or benzodiazepines.Label,15,16,17,18,19,20,21

Mechanism of action

Fentanyl binds to opioid receptors, especially the mu opioid receptor, which are coupled to G-proteins.6 Activation of opioid receptors causes GTP to be exchanged for GDP on the G-proteins which in turn down regulates adenylate cyclase, reducing concentrations of cAMP.6 Reduced cAMP decreases cAMP dependant influx of calcium ions into the cell.6 The exchange of GTP for GDP results in hyperpolarization of the cell and inhibition of nerve activity.6

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
ADelta-type opioid receptor
agonist
Humans
UKappa-type opioid receptor
agonist
Humans
UP-glycoprotein 1Not AvailableHumans
Absorption

Fentanyl sublingual tablets are 54% bioavailable15, transmucosal lozenges are 50% bioavailable16, buccal tablets are 65% bioavailable17, sublingual spray is 76% bioavailable18, and nasal spray is 20% more bioavailable than transmucosal20 (or approximately 64% bioavailable).

Fentanyl transmucosal lozenges reach a Cmax of 0.4±0.1ng/mL for a 200µg dose and 2.5±0.6ng/mL for a 1600µg dose with a Tmax of 20-40 minutes.11 The AUC was 172±96ng*min/mL for a 200µg dose and 1508±1360ng*min/mL for a 1600µg dose.11

Fentanyl sublingual spray reached a Cmax of 0.20±0.06ng/mL for a 100µg dose and 1.61±0.60ng/mL for an 800µg dose with a Tmax of 0.69-1.25 hours, decreasing as the dose increased.12 The AUC was 1.25±0.67ng*h/mL for a 100µg dose and 10.38±3.70ng*h/mL for a 800µg dose.12

Fentanyl transdermal systems reached a Cmax of 0.24±0.20ng/mL with a Tmax of 3.6±1.3h for a 25µg/h dose.13 The AUC was 0.42±0.35ng/mL*h.13

Fentanyl nasal spray reaches a Cmax of 815±301pg/mL with a Tmax of less than 1 hour for a 200µg/100µL dose.14 The AUC was 3772pg*h/mL.14

Volume of distribution

The intravenous volume of distribution is 4L/kg (3-8L/kg)Label,19. The oral volume of distribution is 25.4L/kg.17 In hepatically impaired patients, the intravenous volume of distribution ranges from 0.8-8L/kg.19

Fentanyl crosses the blood brain barrier9 and the placenta.10

Protein binding

Fentanyl is 80-85% bound to plasma proteins.15,16,17,18,20 In one study, a 0.1µg/L solution of fentanyl was 77.9±1.1% bound to human serum albumin and 12.0±5.4% bound to α-1 acid glycoprotein.7 A 0.1µg/L solution of norfentanyl, the primary metabolite of fentanyl, was 7.62±1.2% bound to human serum albumin and 7.24±1.9% bound to α-1 acid glycoprotein.7

Metabolism

Fentanyl is metabolized to a number of inactive metabolites.5 Fentanyl is 99% N-dealkylated to norfentanyl by cytochrome P450.5 It can also be amide hydrolyzed to despropionylfentanyl, or alkyl hydroxylated to hydroxyfentanyl which is N-dealkylated to hydroxynorfentanyl.5

Hover over products below to view reaction partners

Route of elimination

Within 72 hours, 75% of a dose of fentanyl is excreted in the urine with <7% unchanged, and 9% is excreted in the feces with <1% unchanged.Label,15,19

Half-life

The half life of fentanyl is 7 hours.16 The half life of fentanyl sublingual spray is 5-12 hours.18

Clearance

Total plasma clearance of fentanyl is 0.5L/hr/kg (0.3-0.7L/hr/kg)16 or 42L/hr.17,20 Following an intravenous dose, surgical patients displayed a clearance of 27-75L/h, hepatically impaired patients displayed a clearance of 3-80L/h, and renally impaired patients displayed a clearance of 30-78L/h.19

Adverse Effects
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Toxicity

Fentanyl has an intravenous LD50 of 2.91mg/kg in rats1, an oral LD50 of 18mg/kg in rats and 368mg/kg in mice.MSDS The LD50 in humans is not known.

Symptoms of overdose include respiratory depression, somnolence, stupor, coma, skeletal muscle flaccidity, cold and clammy skin, pupillary constriction, pulmonary edema, bradycardia, hypotension, airway obstruction, atypical snoring, and death.Label,15,16,17,18,19,20 In case of overdose, patients should receive naloxone or nalmefene to reverse the action of the opioids as well as supportive measures to maintain the airway or advanced life support in the case of cardiac arrest.Label,15,16,17,18,19,20

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Fentanyl Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 3A4CYP3A4*20Not Available1461_1462insAADR InferredPoor drug metabolizer, increased adverse drug effects, risk of potentially fatal respiratory depression.Details
Cytochrome P450 3A4CYP3A4*26Not Available802C>TADR InferredPoor drug metabolizer, increased adverse drug effects, risk of potentially fatal respiratory depression.Details

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirFentanyl may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe metabolism of Fentanyl can be decreased when combined with Abametapir.
AbataceptThe metabolism of Fentanyl can be increased when combined with Abatacept.
AcalabrutinibThe metabolism of Fentanyl can be decreased when combined with Acalabrutinib.
AcarboseAcarbose may decrease the excretion rate of Fentanyl which could result in a higher serum level.
AcebutololFentanyl may decrease the antihypertensive activities of Acebutolol.
AceclofenacFentanyl may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
AcemetacinFentanyl may decrease the excretion rate of Acemetacin which could result in a higher serum level.
AcenocoumarolThe risk or severity of adverse effects can be increased when Fentanyl is combined with Acenocoumarol.
AcetaminophenThe metabolism of Fentanyl can be decreased when combined with Acetaminophen.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid alcohol.

Products

Product Ingredients
IngredientUNIICASInChI Key
Fentanyl citrateMUN5LYG46H990-73-8IVLVTNPOHDFFCJ-UHFFFAOYSA-N
Fentanyl hydrochloride59H156XY461443-54-5LHCBOXPPRUIAQT-UHFFFAOYSA-N
Product Images
International/Other Brands
Durogesic (Janssen) / Fentanest (Pfizer) / Nasalfent (Archimedes) / Rapinyl (Gedeon Richter)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AbstralTablet600 ug/1SublingualProstrakan Pharmaceuticals2011-01-07Not applicableUS flag
AbstralTablet200 ug/1SublingualProstrakan Pharmaceuticals2011-01-07Not applicableUS flag
AbstralTablet400 mcgSublingualPaladin Labs Inc2011-04-182018-06-29Canada flag
AbstralTablet100 mcgSublingualPaladin Labs Inc2011-04-182018-06-29Canada flag
AbstralTablet600 ug/1SublingualGalena Biopharma, Inc.2013-08-08Not applicableUS flag
AbstralTablet200 ug/1SublingualGalena Biopharma, Inc.2013-08-08Not applicableUS flag
AbstralTablet400 ug/1SublingualProstrakan Pharmaceuticals2011-01-07Not applicableUS flag
AbstralTablet100 ug/1SublingualProstrakan Pharmaceuticals2011-01-07Not applicableUS flag
AbstralTablet400 ug/1SublingualGalena Biopharma, Inc.2013-08-08Not applicableUS flag
AbstralTablet300 mcgSublingualPaladin Labs Inc2011-04-182018-06-29Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-fentanyl MatrixPatchTransdermalApotex Corporation2009-05-132018-07-12Canada flag
Apo-fentanyl MatrixPatchTransdermalApotex Corporation2009-05-132018-07-12Canada flag
Apo-fentanyl MatrixPatchTransdermalApotex Corporation2009-05-132018-02-20Canada flag
Apo-fentanyl MatrixPatchTransdermalApotex CorporationNot applicableNot applicableCanada flag
Apo-fentanyl MatrixPatchTransdermalApotex Corporation2009-05-132018-07-12Canada flag
FentanylPatch, extended release100 ug/1hTransdermalLake Erie Medical DBA Quality Care Products LLC2011-12-092014-12-31US flag
FentanylPatch, extended release25 ug/1hTransdermalQuality Care Products, LLC2019-05-17Not applicableUS flag
FentanylPatch, extended release50 ug/1hTransdermalDirectrx2015-01-01Not applicableUS flag
FentanylPatch, extended release75 ug/1hTransdermalApotex Corp.2010-03-012018-05-29US flag
FentanylPatch, extended release100 ug/1hTransdermalApotex Corp.2013-04-04Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Innovar InjFentanyl citrate (.05 mg) + Droperidol (2.5 mg)LiquidIntramuscular; IntravenousJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1982-12-311996-09-10Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Fentanyl CitrateFentanyl citrate (5 ug/1mL)Injection, solutionIntravenousCantrell Drug Company2013-11-22Not applicableUS flag
Fentanyl CitrateFentanyl citrate (10 ug/1mL)Injection, solutionEpidural; IntravenousCantrell Drug Company2013-04-232017-12-06US flag
Fentanyl CitrateFentanyl citrate (50 ug/1mL)Injection, solutionIntravenousCantrell Drug Company2013-10-112017-12-06US flag
Fentanyl CitrateFentanyl citrate (50 ug/1mL)Injection, solutionIntravenousCantrell Drug Company2011-10-20Not applicableUS flag
Fentanyl CitrateFentanyl citrate (25 ug/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-212017-12-06US flag
Fentanyl CitrateFentanyl citrate (20 ug/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUS flag
Fentanyl Citrate, Bupivacaine HClFentanyl citrate (3 ug/1mL) + Bupivacaine hydrochloride (1.25 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2013-12-18Not applicableUS flag
Fentanyl Citrate, Bupivacaine HClFentanyl citrate (1 ug/1mL) + Bupivacaine hydrochloride (1.25 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2013-08-12Not applicableUS flag
Fentanyl Citrate, Bupivacaine HClFentanyl citrate (2 ug/1mL) + Bupivacaine hydrochloride (1 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2013-09-092017-12-06US flag
Fentanyl Citrate, Bupivacaine HClFentanyl citrate (2 ug/1mL) + Bupivacaine hydrochloride (1.25 mg/1mL)Injection, solutionEpiduralCantrell Drug Company2013-03-25Not applicableUS flag

Categories

ATC Codes
N01AH01 — FentanylN02AB03 — FentanylN01AH51 — Fentanyl, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Phenethylamines / Anilides / Aralkylamines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Amine / Amino acid or derivatives / Anilide / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Carboxylic acid derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, monocarboxylic acid amide, anilide (CHEBI:119915)

Chemical Identifiers

UNII
UF599785JZ
CAS number
437-38-7
InChI Key
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

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. Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. [PubMed:18001263]
  3. 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]
  4. Roy SD, Flynn GL: Solubility behavior of narcotic analgesics in aqueous media: solubilities and dissociation constants of morphine, fentanyl, and sufentanil. Pharm Res. 1989 Feb;6(2):147-51. [PubMed:2569731]
  5. DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ: Metabolism and Disposition of Prescription Opioids: A Review. Forensic Sci Rev. 2015 Jul;27(2):115-45. [PubMed:26227254]
  6. Al-Hasani R, Bruchas MR: Molecular mechanisms of opioid receptor-dependent signaling and behavior. Anesthesiology. 2011 Dec;115(6):1363-81. doi: 10.1097/ALN.0b013e318238bba6. [PubMed:22020140]
  7. Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R: Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and alpha-1 acid glycoprotein. Xenobiotica. 2015 Mar;45(3):207-12. doi: 10.3109/00498254.2014.971093. Epub 2014 Oct 14. [PubMed:25314012]
  8. Raffa RB, Pergolizzi JV Jr, LeQuang JA, Taylor R Jr, Colucci S, Annabi MH: The fentanyl family: A distinguished medical history tainted by abuse. J Clin Pharm Ther. 2018 Feb;43(1):154-158. doi: 10.1111/jcpt.12640. Epub 2017 Oct 4. [PubMed:28980330]
  9. Schaefer CP, Tome ME, Davis TP: The opioid epidemic: a central role for the blood brain barrier in opioid analgesia and abuse. Fluids Barriers CNS. 2017 Nov 29;14(1):32. doi: 10.1186/s12987-017-0080-3. [PubMed:29183383]
  10. Cooper J, Jauniaux E, Gulbis B, Quick D, Bromley L: Placental transfer of fentanyl in early human pregnancy and its detection in fetal brain. Br J Anaesth. 1999 Jun;82(6):929-31. doi: 10.1093/bja/82.6.929. [PubMed:10562792]
  11. Streisand JB, Busch MA, Egan TD, Smith BG, Gay M, Pace NL: Dose proportionality and pharmacokinetics of oral transmucosal fentanyl citrate. Anesthesiology. 1998 Feb;88(2):305-9. [PubMed:9477048]
  12. Parikh N, Goskonda V, Chavan A, Dillaha L: Pharmacokinetics and dose proportionality of fentanyl sublingual spray: a single-dose 5-way crossover study. Clin Drug Investig. 2013 Jun;33(6):391-400. doi: 10.1007/s40261-013-0079-8. [PubMed:23605506]
  13. Ashburn MA, Ogden LL, Zhang J, Love G, Basta SV: The pharmacokinetics of transdermal fentanyl delivered with and without controlled heat. J Pain. 2003 Aug;4(6):291-7. [PubMed:14622685]
  14. Nave R, Schmitt H, Popper L: Faster absorption and higher systemic bioavailability of intranasal fentanyl spray compared to oral transmucosal fentanyl citrate in healthy subjects. Drug Deliv. 2013 Jun-Jul;20(5):216-23. doi: 10.3109/10717544.2012.762435. Epub 2013 May 8. [PubMed:23650968]
  15. FDA Approved Drug Products: Abstral Sublingual Tablet [Link]
  16. FDA Approved Drug Products: Actiq Transmucosal Lozenge [Link]
  17. FDA Approved Drug Products: Fentora Buccal Tablet [Link]
  18. FDA Approved Drug Products: Subsys Sublingual Spray [Link]
  19. FDA Approved Drug Products: Duragesic Transdermal System [Link]
  20. FDA Approved Drug Products: Lazanda Metered Nasal Spray [Link]
  21. FDA Approved Drug Products: Sublimaze Preservative Free Intramuscular and Intravenous Injection [Link]
  22. CDC Drug Overdose Deaths 2017 [Link]
  23. Government of Canada: Canada's opioid crisis [Link]
Human Metabolome Database
HMDB0014951
KEGG Drug
D00320
PubChem Compound
3345
PubChem Substance
46506372
ChemSpider
3228
BindingDB
50008984
RxNav
4337
ChEBI
119915
ChEMBL
CHEMBL596
ZINC
ZINC000002522669
Therapeutic Targets Database
DAP000072
PharmGKB
PA449599
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
7V7
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fentanyl
AHFS Codes
  • 28:08.08 — Opiate Agonists
PDB Entries
5tzo
FDA label
Download (203 KB)
MSDS
Download (75.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentAcute Lung Injury (ALI) / Acute Respiratory Distress Syndrome (ARDS) / Illness, Critical / Sleep1
4Active Not RecruitingTreatmentAnaesthesia therapy1
4Active Not RecruitingTreatmentImmunosuppression / Neoplasms, Lung / Pain1
4Active Not RecruitingTreatmentOocyte Retrieval / Postoperative pain1
4Active Not RecruitingTreatmentSupracondylar Fractures1
4CompletedNot AvailableBack Pain Lower Back2
4CompletedNot AvailableDigestive System Diseases / Disorientation1
4CompletedNot AvailableFailed Moderate Sedation During Procedure1
4CompletedNot AvailableHemorrhoids / Peri Anal Fistula1
4CompletedNot AvailableOsteoarthritis in the Hip Joint / Osteoarthritis of the Knee / Pain1

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
FormRouteStrength
TabletSublingual100 MCG
TabletSublingual100 ug/1
TabletSublingual200 MCG
TabletSublingual200 ug/1
TabletSublingual300 MCG
TabletSublingual300 ug/1
TabletSublingual400 MCG
TabletSublingual400 ug/1
TabletSublingual600 MCG
TabletSublingual600 ug/1
TabletSublingual800 MCG
TabletSublingual800 ug/1
Tablet
Tablet, orally disintegratingSublingual100 ug/1
Tablet, orally disintegratingSublingual200 ug/1
Tablet, orally disintegratingSublingual300 ug/1
Tablet, orally disintegratingSublingual400 ug/1
Tablet, orally disintegratingSublingual600 ug/1
Tablet, orally disintegratingSublingual800 ug/1
TabletOral; Transmucosal1200 MICROGRAMMI
TabletOral; Transmucosal1600 MICROGRAMMI
TabletOral; Transmucosal200 MICROGRAMMI
TabletOral; Transmucosal400 MICROGRAMMI
TabletOral; Transmucosal600 MICROGRAMMI
TabletOral; Transmucosal800 MICROGRAMMI
InjectionParenteral0.5 mg
PatchTransdermal100 mcg
PatchTransdermal12 mcg
PatchTransdermal25 mcg
PatchTransdermal50 mcg
PatchTransdermal75 mcg
Patch, extended releaseTransdermal12.5 ug/1h
PatchTransdermal100 ug/1
PatchTransdermal12.5 ug/1
PatchTransdermal25 ug/1
PatchTransdermal50 ug/1
PatchTransdermal75 ug/1
PatchTransdermal100 μg/h
PatchTransdermal16.8 mg
PatchTransdermal12 μg/h
PatchTransdermal25 μg/h
PatchTransdermal50 μg/h
PatchTransdermal75 μg/h
PlasterCutaneous16.8 mg/1
PlasterCutaneous16.8 MG
PlasterCutaneous100 UG
PlasterCutaneous2.1 MG
PlasterCutaneous12 UG
PlasterCutaneous4.2 MG
PlasterCutaneous4.2 mg/1
PlasterCutaneous25 UG
PlasterCutaneous8.4 MG
PlasterCutaneous50 UG
PlasterCutaneous12.6 MG
PlasterCutaneous75 UG
PlasterCutaneous12.6 mg/1
PatchTransdermal8.4 mg
PatchTransdermal12.6 mg
Drug delivery systemTransdermal4.2 mg
TabletBuccal100 micrograms
TabletBuccal200 micrograms
TabletBuccal400 micrograms
TabletBuccal600 micrograms
TabletBuccal800 micrograms
TabletOral; Transmucosal100 MCG
TabletOral; Transmucosal200 MCG
TabletOral; Transmucosal400 MCG
TabletOral; Transmucosal600 MCG
TabletOral; Transmucosal800 MCG
TabletBuccal100 mcg
TabletBuccal200 mcg
TabletBuccal400 mcg
TabletBuccal800 mcg
SolutionIntramuscular; Intravenous0.5 mg
PlasterCutaneous37.5 UG
Injection, solutionParenteral0.1 MG/2ML
SolutionIntravenous0.1 mg
InjectionIntravenous0.5 mg
SolutionIntravenous0.5 mg
PatchTransdermal1.28 mg/1[USP'U]
PatchTransdermal10.20 mg/1[USP'U]
PatchTransdermal12 ug/1h
PatchTransdermal12 ug/1
PatchTransdermal12.5 ug/1h
PatchTransdermal2.55 mg/1[USP'U]
PatchTransdermal37.5 ug/1h
PatchTransdermal5.10 mg/1[USP'U]
PatchTransdermal62.5 ug/1h
PatchTransdermal7.65 mg/1[USP'U]
PatchTransdermal87.5 ug/1h
Patch, extended releaseTransdermal100 ug/1h
Patch, extended releaseTransdermal12 ug/1h
Patch, extended releaseTransdermal2.5 mg/72h
Patch, extended releaseTransdermal25 ug/1h
Patch, extended releaseTransdermal37.5 ug/1h
Patch, extended releaseTransdermal5.0 mg/72h
Patch, extended releaseTransdermal62.5 ug/1h
Patch, extended releaseTransdermal7.5 mg/72h
Patch, extended releaseTransdermal75 ug/1h
Patch, extended releaseTransdermal87.5 ug/1h
SolutionIntravenous0.05 mg/ml
PlasterCutaneous150 UG
SolutionIntravenous0.785 mg
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
TabletBuccal; Sublingual100 ug/1
TabletBuccal; Sublingual200 ug/1
TabletBuccal; Sublingual400 ug/1
TabletBuccal; Sublingual600 ug/1
TabletBuccal; Sublingual800 ug/1
InjectionIntramuscular; Intravenous50 ug/1mL
InjectionIntravenous50 ug/1mL
Injection, solutionEpidural; Intravenous10 ug/1mL
Injection, solutionIntramuscular; Intravenous0.05 mg/1mL
Injection, solutionIntravenous20 ug/1mL
Injection, solutionIntravenous25 ug/1mL
Injection, solutionIntravenous5 ug/1mL
Injection, solutionIntravenous50 ug/1mL
LozengeOral; Transmucosal1200 ug/1
LozengeOral; Transmucosal1600 ug/1
LozengeOral; Transmucosal200 ug/1
LozengeOral; Transmucosal800 ug/1
LozengeTransmucosal1200 ug/1
LozengeTransmucosal1600 ug/1
LozengeTransmucosal200 ug/1
LozengeTransmucosal400 ug/1
LozengeTransmucosal600 ug/1
LozengeTransmucosal800 ug/1
SolutionEpidural; Intramuscular; Intravenous
LiquidEpidural; Intramuscular; Intravenous
Injection, solutionEpidural
Injection, solutionParenteral50 MICROGRAMMI/ML
Injection, solutionIntravenous100 mg/2ml
Injection, solutionIntravenous500 mg/10ml
PatchTransdermal100 ug/1h
PatchTransdermal25 ug/1h
PatchTransdermal50 ug/1h
PatchTransdermal75 ug/1h
Patch, extended releaseTransdermal50 ug/1h
Patch, extended releaseTransdermal
PlasterCutaneous100 MIKROGRAMM
PlasterCutaneous12 MIKROGRAMM
PlasterCutaneous25 MIKROGRAMM
PlasterCutaneous50 MIKROGRAMM
PlasterCutaneous75 MIKROGRAMM
Injection, solutionIntramuscular; Intravenous0.1 mg/2ml
Injection, solutionIntramuscular; Intravenous0.5 mg/10ml
TabletBuccal; Oral; Transmucosal300 ug/1
Tablet, effervescentBuccal; Sublingual100 mcg
Tablet, effervescentBuccal; Sublingual200 mcg
Tablet, effervescentBuccal; Sublingual400 mcg
Tablet, effervescentBuccal; Sublingual600 mcg
Tablet, effervescentBuccal; Sublingual800 mcg
LiquidIntramuscular; Intravenous
SolutionNasal100 mcg
SolutionNasal200 mcg
SolutionNasal50 mcg
SprayNasal100 MCG
SprayNasal2 mg/1mL
SprayNasal200 MCG
SprayNasal50 MCG
PatchTransdermal40 μg/dose
PatchTransdermal40 ug/1
Patch, extended release, electrically controlledTransdermal40 ug/10min
SolutionParenteral0.1 mg
SolutionParenteral250 mcg
SprayNasal100 ug/1
SprayNasal300 ug/1
SprayNasal400 ug/1
Film, solubleBuccal1200 mcg
Film, solubleBuccal1200 ug/1
Film, solubleBuccal200 mcg
Film, solubleBuccal200 ug/1
Film, solubleBuccal400 ug/1
Film, solubleBuccal400 mcg
Film, solubleBuccal600 ug/1
Film, solubleBuccal600 mcg
Film, solubleBuccal800 mcg
Film, solubleBuccal800 ug/1
Injection, solutionIntramuscular; Intravenous50 ug/1mL
SpraySublingual0.1 mg/1
SpraySublingual0.2 mg/1
SpraySublingual0.4 mg/1
SpraySublingual0.6 mg/1
SpraySublingual0.8 mg/1
Injection
Injection0.1 mg/2ml
Injection0.5 mg/10ml
PatchTransdermal
LozengeOral; Transmucosal1200 1/1
LozengeOral; Transmucosal400 ug/1
LozengeOral; Transmucosal600 ug/1
TabletSublingual133 MICROGRAMMI
TabletSublingual267 MICROGRAMMI
TabletSublingual400 MICROGRAMMI
TabletSublingual533 MICROGRAMMI
TabletSublingual67 MICROGRAMMI
TabletSublingual800 MICROGRAMMI
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)Region
US6317629No2001-11-132012-06-02US flag
US6200604No2001-03-132019-03-26US flag
US6974590No2005-12-132019-03-26US flag
US8728441No2014-05-202019-03-26US flag
US8753611No2014-06-172019-03-26US flag
US8765100No2014-07-012019-03-26US flag
US7862833No2011-01-042028-06-15US flag
US8119158No2012-02-212024-12-30US flag
US8092832No2012-01-102024-12-30US flag
US7862832No2011-01-042028-06-15US flag
US6761910No2004-07-132019-09-24US flag
US6195582No2001-02-272019-01-28US flag
US6881208No2005-04-192022-04-19US flag
US8428709No2013-04-232032-06-11US flag
US8428708No2013-04-232032-05-21US flag
US6169920No2001-01-022018-01-02US flag
US8781571No2014-07-152032-03-31US flag
US6181963No2001-01-302019-11-02US flag
US5843014No1998-12-012015-12-01US flag
US5697896No1997-12-162016-12-16US flag
US6975902No2005-12-132024-04-01US flag
US8301238No2012-10-302031-09-30US flag
US9095706No2015-08-042033-02-03US flag
US7579019No2009-08-252020-01-22US flag
US6159498No2000-12-122016-10-18US flag
US6759059No2004-07-062019-09-24US flag
US7910132No2011-03-222019-09-24US flag
US8889176No2014-11-182024-01-16US flag
US6432440No2002-08-132018-04-20US flag
US8216604No2012-07-102024-10-03US flag
US9078814No2015-07-142024-01-08US flag
US8486973No2013-07-162030-04-27US flag
US8835460No2014-09-162027-01-25US flag
US8835459No2014-09-162027-01-25US flag
US9241935No2016-01-262027-01-25US flag
US8486972No2013-07-162030-04-27US flag
US9364656No2016-06-142031-09-30US flag
US9597288No2017-03-212027-07-23US flag
US9642844No2017-05-092027-01-25US flag
US9289387No2016-03-222027-01-25US flag
US9642797No2017-05-092027-01-25US flag
US9731869No2017-08-152032-01-26US flag
US9731121No2017-08-152031-10-17US flag
US9814705No2017-11-142024-01-08US flag
US10016403No2018-07-102027-01-25US flag
US10610523No2007-01-252027-01-25US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)83-84 US. Patent 3,141,823.
water solubility0.74mg/mLhttps://www.ncbi.nlm.nih.gov/pubmed/2569731
logP4.05SANGSTER (1993)
pKa8.99https://www.ncbi.nlm.nih.gov/pubmed/2569731
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
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0002-9850000000-7ce3a6f35f5dee98185f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-62593b54c6285a566893
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0209000000-d550d803c25d31570227
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0901000000-09bd125eea134f8811a4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-2c34993eade063cb426f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001r-0900000000-beb72ea99dc9c125d29b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0009000000-bf70e4d857c26d30032f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0907000000-a9f5d0c422eff1474d38
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-0c03ba9ef576114a9503
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0900000000-d2a36b402c3a7424fab6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-1900000000-e0cbdfad80c306baabc1
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-2900000000-ea551550ac6cbe6d3960
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0pdi-8900000000-89b1a77e558ec74cf3ac
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0kdj-9400000000-358833c028a079789d0b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0ufs-9200000000-ff2c211a084a5f124781

Targets

Details
1. Mu-type opioid receptor
Kind
Protein
Organism
Humans
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...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
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
Humans
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 n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
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
Humans
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 synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
Uniprot Name
Multidrug resistance protein 1
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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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]
  2. Feierman DE, Lasker JM: Metabolism of fentanyl, a synthetic opioid analgesic, by human liver microsomes. Role of CYP3A4. Drug Metab Dispos. 1996 Sep;24(9):932-9. [PubMed:8886601]
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R: Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and alpha-1 acid glycoprotein. Xenobiotica. 2015 Mar;45(3):207-12. doi: 10.3109/00498254.2014.971093. Epub 2014 Oct 14. [PubMed:25314012]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R: Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and alpha-1 acid glycoprotein. Xenobiotica. 2015 Mar;45(3):207-12. doi: 10.3109/00498254.2014.971093. Epub 2014 Oct 14. [PubMed:25314012]

Transporters

Details
1. P-glycoprotein 1
Kind
Protein
Organism
Humans
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
Uniprot Name
Multidrug resistance protein 1
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]

Drug created on June 13, 2005 07:24 / Updated on September 24, 2020 02:08

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