Fentanyl
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Identification
- Summary
Fentanyl is an opioid analgesic used in anesthesia, for breakthrough cancer pain, or round the clock pain management.
- Brand Names
- Abstral, Actiq, Duragesic, Effentora, Fentora, Instanyl, Lazanda, Sublimaze, Subsys
- Generic Name
- Fentanyl
- DrugBank Accession Number
- DB00813
- Background
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
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Breakthrough cancer pain •••••••••••• •••••••• •••••• •••••• •••••••• •••••• Treatment of Severe chronic pain •••••••••••• •••• - Associated Therapies
- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
Target Actions Organism AMu-type opioid receptor agonistHumans ADelta-type opioid receptor agonistHumans UKappa-type opioid receptor agonistHumans UATP-dependent translocase ABCB1 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Pathways
Pathway Category Fentanyl Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 3A4 CYP3A4*20 Not Available 1461_1462insA ADR Inferred Poor drug metabolizer, increased adverse drug effects, risk of potentially fatal respiratory depression. Details Cytochrome P450 3A4 CYP3A4*26 Not Available 802C>T ADR Inferred Poor 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Fentanyl is combined with 1,2-Benzodiazepine. Abacavir Fentanyl may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Fentanyl can be increased when it is combined with Abametapir. Abatacept The metabolism of Fentanyl can be increased when combined with Abatacept. Acebutolol Fentanyl may decrease the antihypertensive activities of Acebutolol. - Food Interactions
- Avoid alcohol.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Fentanyl citrate MUN5LYG46H 990-73-8 IVLVTNPOHDFFCJ-UHFFFAOYSA-N Fentanyl hydrochloride 59H156XY46 1443-54-5 LHCBOXPPRUIAQT-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Durogesic (Janssen) / Fentanest (Pfizer) / Nasalfent (Archimedes) / Rapinyl (Gedeon Richter)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Abstral Tablet 800 ug/1 Sublingual Galena Biopharma, Inc. 2013-08-08 Not applicable US Abstral Tablet 600 ug/1 Sublingual Prostrakan Pharmaceuticals 2011-01-07 Not applicable US Abstral Tablet 300 ug/1 Sublingual Galena Biopharma, Inc. 2013-08-08 Not applicable US Abstral Tablet 200 ug/1 Sublingual Prostrakan Pharmaceuticals 2011-01-07 Not applicable US Abstral Tablet 800 mcg Sublingual Paladin Labs Inc. 2011-06-03 2018-06-29 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-fentanyl Matrix Patch 75 mcg / hour Transdermal Apotex Corporation 2009-05-13 2018-07-12 Canada Apo-fentanyl Matrix Patch 50 mcg / hour Transdermal Apotex Corporation 2009-05-13 2018-02-20 Canada Apo-fentanyl Matrix Patch 12 mcg / hour Transdermal Apotex Corporation Not applicable Not applicable Canada Apo-fentanyl Matrix Patch 25 mcg / hour Transdermal Apotex Corporation 2009-05-13 2018-07-12 Canada Apo-fentanyl Matrix Patch 100 mcg / hour Transdermal Apotex Corporation 2009-05-13 2018-07-12 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Innovar Inj Fentanyl citrate (.05 mg / mL) + Droperidol (2.5 mg / mL) Liquid Intramuscular; Intravenous Janssen Pharmaceutica, Division Of Janssen Ortho Inc. 1982-12-31 1996-09-10 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Fentanyl Citrate Fentanyl citrate (10 ug/1mL) Injection, solution Epidural; Intravenous Cantrell Drug Company 2013-04-23 2017-12-06 US Fentanyl Citrate Fentanyl citrate (50 ug/1mL) Injection, solution Intravenous Cantrell Drug Company 2013-10-11 2017-12-06 US Fentanyl Citrate Fentanyl citrate (50 ug/1mL) Injection, solution Intravenous Cantrell Drug Company 2011-10-20 Not applicable US Fentanyl Citrate Fentanyl citrate (25 ug/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-21 2017-12-06 US Fentanyl Citrate Fentanyl citrate (20 ug/1mL) Injection, solution Intravenous Cantrell Drug Company 2014-08-13 Not applicable US
Categories
- ATC Codes
- N01AH01 — FentanylN02AB03 — FentanylN01AH51 — Fentanyl, combinations
- Drug Categories
- Adjuvants
- Adjuvants, Anesthesia
- Agents that produce hypertension
- Agents that reduce seizure threshold
- Analgesics
- Anesthetics
- Anesthetics, General
- Anesthetics, Intravenous
- Antidepressive Agents
- Bradycardia-Causing Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Substrates
- Drugs that are Mainly Renally Excreted
- Fentanyl and fentanyl analogues
- High-risk opioids
- Narcotics
- Nervous System
- Neuraxial Anesthetics
- Opiate Agonists
- Opioid Agonist
- Opioid Anesthetics
- Opioids
- Opioids, Anilidopiperidine
- P-glycoprotein inhibitors
- Peripheral Nervous System Agents
- Phenylpiperidine opioids
- Piperidines
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Modulators
- 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)
- Affected organisms
- Humans and other mammals
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
- 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. [Article]
- Taylor DR: Fentanyl buccal tablet: rapid relief from breakthrough pain. Expert Opin Pharmacother. 2007 Dec;8(17):3043-51. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- FDA Approved Drug Products: Abstral Sublingual Tablet [Link]
- FDA Approved Drug Products: Actiq Transmucosal Lozenge [Link]
- FDA Approved Drug Products: Fentora Buccal Tablet [Link]
- FDA Approved Drug Products: Subsys Sublingual Spray [Link]
- FDA Approved Drug Products: Duragesic Transdermal System [Link]
- FDA Approved Drug Products: Lazanda Metered Nasal Spray [Link]
- FDA Approved Drug Products: Sublimaze Preservative Free Intramuscular and Intravenous Injection [Link]
- CDC Drug Overdose Deaths 2017 [Link]
- Government of Canada: Canada's opioid crisis [Link]
- FDA Approved Drug Products: ACTIQ® (fentanyl citrate) oral transmucosal lozenge, CII (Jan 2024) [Link]
- External Links
- Human Metabolome Database
- HMDB0014951
- KEGG Drug
- D00320
- PubChem Compound
- 3345
- PubChem Substance
- 46506372
- ChemSpider
- 3228
- BindingDB
- 50008984
- 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
- PDB Entries
- 5tzo / 7qt2 / 7qt3 / 7u64 / 8ef5 / 8tfq / 8v9w / 8v9x / 8v9z / 8va0 … show 3 more
- FDA label
- Download (203 KB)
- MSDS
- Download (75.5 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Respiratory Depression 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Prevention Alzheimer's Disease (AD) / Dementia 1 somestatus stop reason just information to hide Not Available Active Not Recruiting Supportive Care Separation Anxiety 1 somestatus stop reason just information to hide Not Available Completed Not Available AAT Deficiency / AATD / Alpha-1 Anti-trypsin Deficiency / Liver Fibrosis 1 somestatus stop reason just information to hide Not Available Completed Not Available Acute Lymphocytic Leukemia, Pediatric / Anesthesia therapy / Pain 1 somestatus stop reason just information to hide
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 mcg Tablet Sublingual 100 ug/1 Tablet Sublingual 200 mcg Tablet Sublingual 200 ug/1 Tablet Sublingual 300 ug/1 Tablet Sublingual 300 mcg Tablet Sublingual 400 ug/1 Tablet Sublingual 400 mcg Tablet Sublingual 600 mcg Tablet Sublingual 600 ug/1 Tablet Sublingual 800 mcg Tablet Sublingual 800 ug/1 Tablet, orally disintegrating Sublingual 100 ug/1 Tablet, orally disintegrating Sublingual 200 ug/1 Tablet, orally disintegrating Sublingual 300 ug/1 Tablet, orally disintegrating Sublingual 400 ug/1 Tablet, orally disintegrating Sublingual 600 ug/1 Tablet, orally disintegrating Sublingual 800 ug/1 Lozenge Transmucosal 1200 mcg Lozenge Transmucosal 1600 mcg Lozenge Transmucosal 200 mcg Lozenge Transmucosal 400 mcg Lozenge Transmucosal 600 mcg Lozenge Transmucosal 800 mcg Tablet Oral; Transmucosal 1200 MICROGRAMMI Tablet Oral; Transmucosal 1600 MICROGRAMMI Tablet Oral; Transmucosal 200 MICROGRAMMI Tablet Oral; Transmucosal 400 MICROGRAMMI Tablet Oral; Transmucosal 600 MICROGRAMMI Tablet Oral; Transmucosal 800 MICROGRAMMI Lozenge Oral 1200 Mikrogramm Lozenge Oral 1600 Mikrogramm Lozenge Oral 200 Mikrogramm Lozenge Oral 400 Mikrogramm Lozenge Oral 600 Mikrogramm Lozenge Oral 800 Mikrogramm Film Buccal Injection Intramuscular; Intravenous 0.5 mg Injection Parenteral 0.5 mg Solution Intrasinal; Respiratory (inhalation) 100 mcg Tablet 600 MICROGRAMMI Tablet 800 MICROGRAMMI Patch, extended release Transdermal 12.5 ug/1h Patch Transdermal 100 ug/1 Patch Transdermal 12.5 ug/1 Patch Transdermal 25 ug/1 Patch Transdermal 50 ug/1 Patch Transdermal 75 ug/1 Patch Transdermal 100 MCG Patch Transdermal 12 MCG Patch Transdermal 25 MCG Patch Transdermal 50 MCG Patch Transdermal 75 MCG Patch Transdermal 5.5 mg Patch Transdermal 11 mg Patch Transdermal 1.375 mg Patch Transdermal 2.75 mg Patch Transdermal 8.25 mg Patch Transdermal 50 MICROGRAMMI/ORA Patch Transdermal 2.1 mg Patch Transdermal 100 μg/h Plaster Transdermal Patch Transdermal 16.8 mg Patch, extended release Transdermal 12 mcg/hr Patch Transdermal 12 μg/h Patch Transdermal 25 μg/h Patch, extended release Transdermal 25 mcg/hr Patch Transdermal 50 μg/h Patch, extended release Transdermal 50 mcg/hr Patch Transdermal 75 μg/h Patch Transdermal 8.400 mg Plaster Cutaneous 16.8 mg/1 Plaster Cutaneous 16.8 MG Plaster Cutaneous 100 UG Plaster Cutaneous 2.1 MG Plaster Cutaneous 12 UG Plaster Cutaneous 4.2 MG Plaster Cutaneous 4.2 mg/1 Plaster Cutaneous 25 UG Plaster Cutaneous 8.4 MG Plaster Cutaneous 50 UG Plaster Cutaneous 12.6 MG Plaster Cutaneous 75 UG Plaster Cutaneous 12.6 mg/1 Patch Transdermal 4.2 mg Patch Transdermal 8.4 mg Patch Transdermal 12.6 mg Drug delivery system Transdermal 4.2 mg Tablet Buccal 100 micrograms Tablet Buccal 200 micrograms Tablet Buccal 400 micrograms Tablet Buccal 600 micrograms Tablet Buccal 800 micrograms Tablet Oral; Transmucosal 100 MCG Tablet Oral; Transmucosal 200 MCG Tablet Oral; Transmucosal 400 MCG Tablet Oral; Transmucosal 600 MCG Tablet Oral; Transmucosal 800 MCG Tablet Transmucosal 100 MCG Tablet Transmucosal 200 MCG Tablet Buccal 100 mcg Tablet Buccal 200 mcg Tablet Buccal 400 mcg Tablet Buccal 800 mcg Injection 0.0785 mg/2ml Patch Transdermal 2.89 mg Patch Transdermal 5.78 mg/10.5sq cm Patch Transdermal 11.56 mg/21sq cm Tablet Buccal 100 Mikrogramm Tablet Buccal 200 Mikrogramm Tablet Buccal 400 Mikrogramm Tablet Buccal 600 Mikrogramm Tablet Buccal 800 Mikrogramm Plaster Cutaneous 37.5 UG Injection, solution Parenteral 0.1 MG/2ML Tablet Oral 100 MICROGRAMMI Tablet Oral 200 MICROGRAMMI Tablet Oral 400 MICROGRAMMI Tablet Oral 600 MICROGRAMMI Tablet Oral 800 MICROGRAMMI Injection, solution Parenteral Injection, solution 50 MICROGRAMMI/ML Injection Intravenous 0.5 mg Solution Intravenous 500 cg Solution Intramuscular; Intravenous 0.5 mg Solution Intravenous 0.5 mg Solution Intravenous 0.1 mg Solution Intravenous 50 mcg Patch Transdermal 1.28 mg/1[USP'U] Patch Transdermal 10.20 mg/1[USP'U] Patch Transdermal 12 ug/1h Patch Transdermal 12 ug/1 Patch Transdermal 12.5 ug/1h Patch Transdermal 2.55 mg/1[USP'U] Patch Transdermal 37.5 ug/1h Patch Transdermal 5.10 mg/1[USP'U] Patch Transdermal 62.5 ug/1h Patch Transdermal 7.65 mg/1[USP'U] Patch Transdermal 87.5 ug/1h Patch, extended release Transdermal 100 ug/1h Patch, extended release Transdermal 12 ug/1h Patch, extended release Transdermal 2.5 mg/72h Patch, extended release Transdermal 25 ug/1h Patch, extended release Transdermal 37.5 ug/1h Patch, extended release Transdermal 5.0 mg/72h Patch, extended release Transdermal 62.5 ug/1h Patch, extended release Transdermal 7.5 mg/72h Patch, extended release Transdermal 75 ug/1h Patch, extended release Transdermal 87.5 ug/1h Solution Intramuscular; Intravenous 0.1 mg/2ml Solution Intramuscular; Intravenous 0.5 mg/10ml Solution Intravenous 0.05 mg/ml Plaster Cutaneous 150 UG Patch Transdermal Injection Intramuscular; Intravenous 50 mcg/ml Solution Intravenous 0.785 mg 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 Tablet Buccal; Sublingual 100 ug/1 Tablet Buccal; Sublingual 200 ug/1 Tablet Buccal; Sublingual 400 ug/1 Tablet Buccal; Sublingual 600 ug/1 Tablet Buccal; Sublingual 800 ug/1 Injection 0.0785 MG Injection Intramuscular; Intravenous 50 ug/1mL Injection Intravenous 50 ug/1mL Injection, solution Epidural; Intravenous 10 ug/1mL Injection, solution Intramuscular; Intravenous 0.05 mg/1mL Injection, solution Intramuscular; Intravenous 100 ug/2mL Injection, solution Intravenous 20 ug/1mL Injection, solution Intravenous 25 ug/1mL Injection, solution Intravenous 5 ug/1mL Injection, solution Intravenous 50 ug/1mL Lozenge Oral; Transmucosal 1200 ug/1 Lozenge Oral; Transmucosal 1600 ug/1 Lozenge Oral; Transmucosal 200 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 Injection Intramuscular; Intravenous 100 mcg/2ml Solution Epidural; Intramuscular; Intravenous 50 mcg / mL Injection, solution Epidural Plaster Transdermal 100 µg/h Plaster Transdermal 25 µg/h Plaster Transdermal 50 µg/h Plaster Transdermal 75 µg/h Injection, solution Intravenous; Parenteral 50 MCG/ML Injection, solution Parenteral 50 MICROGRAMMI/ML Injection Intramuscular; Intravenous 0.1 mg/2ml Solution Epidural; Intramuscular; Intravenous 100 mcg / 2 mL Solution Epidural; Intramuscular; Intravenous 1000 mcg / 20 mL Solution Epidural; Intramuscular; Intravenous 250 mcg / 5 mL Solution Epidural; Intramuscular; Intravenous 2500 mcg / 50 mL Solution 0.05 mg/mL Injection, solution Parenteral 50 Mikrogramm/ml Injection, solution Intramuscular; Intravenous; Intravenous bolus 0.05 mg/ml Injection, solution Intravenous Injection, solution Intravenous 500 mg/10ml Patch Transdermal 100 ug/1h Patch Transdermal 25 ug/1h Patch Transdermal 50 ug/1h Patch Transdermal 75 ug/1h Patch, extended release Transdermal 50 ug/1h Patch, extended release Transdermal 100 mcg / hour Patch, extended release Transdermal 25 mcg / hour Patch, extended release Transdermal 50 mcg / hour Patch, extended release Transdermal 75 mcg / hour Injection, solution Intramuscular; Intravenous 50 mcg/ml Injection, solution Intravenous 0.05 mg/ml Injection, solution Intramuscular; Intravenous 100 mcg/2ml Injection, solution Intramuscular; Intravenous 500 mcg/10ml Injection 0.05 mg/ml Plaster Cutaneous 100 MIKROGRAMM Plaster Cutaneous 12 MIKROGRAMM Plaster Cutaneous 25 MIKROGRAMM Plaster Cutaneous 50 MIKROGRAMM Plaster Cutaneous 75 MIKROGRAMM Injection, solution Intramuscular; Intravenous 0.1 mg/2ml Injection, solution Intramuscular; Intravenous 0.5 mg/10ml Tablet Buccal; Oral; Transmucosal 300 ug/1 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 Tablet, effervescent Buccal 100 mcg Tablet, effervescent Buccal 200 mcg Tablet, effervescent Buccal 400 mcg Tablet, effervescent Buccal 600 mcg Tablet, effervescent Buccal 800 mcg Patch Transdermal 14.4 mg Liquid Intramuscular; Intravenous Solution Nasal 100 mcg / dose Solution Nasal 200 mcg / dose Solution Nasal 50 mcg / dose Spray Nasal 100 MCG Spray Nasal 2 mg/1mL Spray Nasal 200 MCG Spray Nasal 50 MCG Patch Transdermal 40 μg/dose Patch Transdermal 40 ?g/dose Patch Transdermal 40 ug/1 Patch, extended release, electrically controlled Transdermal 40 ug/10min Solution Parenteral 0.1 mg Solution Intramuscular; Intravenous 250 mcg Spray Nasal 100 ug/1 Spray Nasal 300 ug/1 Spray Nasal 400 ug/1 Injection, solution Intramuscular; Intravenous 50 MCG Film, soluble Buccal 1200 mcg Film, soluble Buccal 1200 ug/1 Film, soluble Buccal 200 mcg Film, soluble Buccal 200 ug/1 Film, soluble Buccal 400 ug/1 Film, soluble Buccal 400 mcg Film, soluble Buccal 600 ug/1 Film, soluble Buccal 600 mcg Film, soluble Buccal 800 ug/1 Film, soluble Buccal 800 mcg Solution Intravenous 0.500 mg Patch Transdermal 12.0 mcg / hour Spray Nasal 400 MCG Spray, metered Nasal 100 mcg Spray, metered Nasal 400 mcg Patch Transdermal 10 mg Patch Transdermal 2.5 mg Patch Transdermal 5 mg Patch Transdermal 7.5 mg Patch Transdermal 37 mcg / hour Tablet 100 MICROGRAMMI Tablet 200 MICROGRAMMI Tablet 300 MICROGRAMMI Tablet 400 MICROGRAMMI Injection, solution Intramuscular; Intravenous 50 ug/1mL Liquid Epidural; Intramuscular; Intravenous 50 mcg / mL Tablet, orally disintegrating Sublingual 100 Mikrogramm Tablet, orally disintegrating Sublingual 200 Mikrogramm Tablet, orally disintegrating Sublingual 400 Mikrogramm Tablet, orally disintegrating Sublingual 600 Mikrogramm Tablet, orally disintegrating Sublingual 800 Mikrogramm Spray Sublingual 0.1 mg/1 Spray Sublingual 0.2 mg/1 Spray Sublingual 0.4 mg/1 Spray Sublingual 0.6 mg/1 Spray Sublingual 0.8 mg/1 Injection, solution Intramuscular; Intravenous Injection, solution 0.1 mg/2ml Injection, solution 0.5 mg/10ml Patch Transdermal 100 mcg / hour Patch Transdermal 12 mcg / hour Patch Transdermal 25 mcg / hour Patch Transdermal 50 mcg / hour Patch Transdermal 75 mcg / hour Tablet Buccal 0.157 mg Lozenge Oral; Transmucosal 1200 1/1 Lozenge Oral; Transmucosal 400 ug/1 Lozenge Oral; Transmucosal 600 ug/1 Injection Parenteral 50 mcg/ml Tablet Sublingual 133 MICROGRAMMI Tablet Sublingual 267 MICROGRAMMI Tablet Sublingual 400 MICROGRAMMI Tablet Sublingual 533 MICROGRAMMI Tablet Sublingual 67 MICROGRAMMI Tablet Sublingual 800 MICROGRAMMI Tablet, orally disintegrating Sublingual - 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) Region US6317629 No 2001-11-13 2012-06-02 US US6200604 No 2001-03-13 2019-03-26 US US6974590 No 2005-12-13 2019-03-26 US US8728441 No 2014-05-20 2019-03-26 US US8753611 No 2014-06-17 2019-03-26 US US8765100 No 2014-07-01 2019-03-26 US US7862833 No 2011-01-04 2028-06-15 US US8119158 No 2012-02-21 2024-12-30 US US8092832 No 2012-01-10 2024-12-30 US US7862832 No 2011-01-04 2028-06-15 US US6761910 No 2004-07-13 2019-09-24 US US6195582 No 2001-02-27 2019-01-28 US US6881208 No 2005-04-19 2022-04-19 US US8428709 No 2013-04-23 2032-06-11 US US8428708 No 2013-04-23 2032-05-21 US US6169920 No 2001-01-02 2018-01-02 US US8781571 No 2014-07-15 2032-03-31 US US6181963 No 2001-01-30 2019-11-02 US US5843014 No 1998-12-01 2015-12-01 US US5697896 No 1997-12-16 2016-12-16 US US6975902 No 2005-12-13 2024-04-01 US US8301238 No 2012-10-30 2031-09-30 US US9095706 No 2015-08-04 2033-02-03 US US7579019 No 2009-08-25 2020-01-22 US US6159498 No 2000-12-12 2016-10-18 US US6759059 No 2004-07-06 2019-09-24 US US7910132 No 2011-03-22 2019-09-24 US US8889176 No 2014-11-18 2024-01-16 US US6432440 No 2002-08-13 2018-04-20 US US8216604 No 2012-07-10 2024-10-03 US US9078814 No 2015-07-14 2024-01-08 US US8486973 No 2013-07-16 2030-04-27 US US8835460 No 2014-09-16 2027-01-25 US US8835459 No 2014-09-16 2027-01-25 US US9241935 No 2016-01-26 2027-01-25 US US8486972 No 2013-07-16 2030-04-27 US US9364656 No 2016-06-14 2031-09-30 US US9597288 No 2017-03-21 2027-07-23 US US9642844 No 2017-05-09 2027-01-25 US US9289387 No 2016-03-22 2027-01-25 US US9642797 No 2017-05-09 2027-01-25 US US9731869 No 2017-08-15 2032-01-26 US US9731121 No 2017-08-15 2031-10-17 US US9814705 No 2017-11-14 2024-01-08 US US10016403 No 2018-07-10 2027-01-25 US US10610523 No 2020-04-07 2027-01-25 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 83-84 US. Patent 3,141,823. water solubility 0.74mg/mL https://www.ncbi.nlm.nih.gov/pubmed/2569731 logP 4.05 SANGSTER (1993) pKa 8.99 https://www.ncbi.nlm.nih.gov/pubmed/2569731 - 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 39.89 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 - 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 197.9301915 predictedDarkChem Lite v0.1.0 [M-H]- 196.7984915 predictedDarkChem Lite v0.1.0 [M-H]- 176.14589 predictedDeepCCS 1.0 (2019) [M+H]+ 198.1062915 predictedDarkChem Lite v0.1.0 [M+H]+ 197.2214915 predictedDarkChem Lite v0.1.0 [M+H]+ 178.50389 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.7531915 predictedDarkChem Lite v0.1.0 [M+Na]+ 185.61565 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for endogenous opioids such as beta-endorphin and endomorphin (PubMed:10529478, PubMed:12589820, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone (PubMed:10529478, PubMed:10836142, PubMed:12589820, PubMed:19300905, PubMed:7891175, PubMed:7905839, PubMed:7957926, PubMed:9689128). Also activated by enkephalin peptides, such as Met-enkephalin or Met-enkephalin-Arg-Phe, with higher affinity for Met-enkephalin-Arg-Phe (By similarity). 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 dissociation of the G-protein complex with the free GTP-bound G-protein alpha and the G-protein beta-gamma dimer activating downstream cellular effectors (PubMed:7905839). The agonist- and cell type-specific activity is predominantly coupled to pertussis toxin-sensitive G(i) and G(o) G alpha proteins, GNAI1, GNAI2, GNAI3 and GNAO1 isoforms Alpha-1 and Alpha-2, and to a lesser extent to pertussis toxin-insensitive G alpha proteins GNAZ and GNA15 (PubMed:12068084). They mediate an array of downstream cellular responses, including inhibition of adenylate cyclase activity and both N-type and L-type calcium channels, activation of inward rectifying potassium channels, mitogen-activated protein kinase (MAPK), phospholipase C (PLC), phosphoinositide/protein kinase (PKC), phosphoinositide 3-kinase (PI3K) and regulation of NF-kappa-B (By similarity). Also couples to adenylate cyclase stimulatory G alpha proteins (By similarity). The selective temporal coupling to G-proteins and subsequent signaling can be regulated by RGSZ proteins, such as RGS9, RGS17 and RGS4 (By similarity). Phosphorylation by members of the GPRK subfamily of Ser/Thr protein kinases and association with beta-arrestins is involved in short-term receptor desensitization (By similarity). Beta-arrestins associate with the GPRK-phosphorylated receptor and uncouple it from the G-protein thus terminating signal transduction (By similarity). The phosphorylated receptor is internalized through endocytosis via clathrin-coated pits which involves beta-arrestins (By similarity). The activation of the ERK pathway occurs either in a G-protein-dependent or a beta-arrestin-dependent manner and is regulated by agonist-specific receptor phosphorylation (By similarity). Acts as a class A G-protein coupled receptor (GPCR) which dissociates from beta-arrestin at or near the plasma membrane and undergoes rapid recycling (By similarity). Receptor down-regulation pathways are varying with the agonist and occur dependent or independent of G-protein coupling (By similarity). Endogenous ligands induce rapid desensitization, endocytosis and recycling (By similarity). Heterooligomerization with other GPCRs can modulate agonist binding, signaling and trafficking properties (By similarity)
- Specific Function
- beta-endorphin receptor activity
- Gene Name
- OPRM1
- Uniprot ID
- P35372
- Uniprot Name
- Mu-type opioid receptor
- 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. [Article]
- Scott LJ, Perry CM: Remifentanil: a review of its use during the induction and maintenance of general anaesthesia. Drugs. 2005;65(13):1793-823. [Article]
- Scott LJ, Perry CM: Spotlight on remifentanil for general anaesthesia. CNS Drugs. 2005;19(12):1069-74. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- G-protein coupled receptor that functions as a 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 neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain and in opiate-mediated analgesia. Plays a role in developing analgesic tolerance to morphine
- Specific Function
- G protein-coupled enkephalin receptor activity
- Gene Name
- OPRD1
- Uniprot ID
- P41143
- Uniprot Name
- Delta-type opioid receptor
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- G-protein coupled opioid receptor that functions as a receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as a 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 the activity of down-stream effectors, such as adenylate cyclase. Signaling leads to the inhibition of adenylate cyclase activity. Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Plays a role in the perception of pain. Plays a role in mediating reduced physical activity upon treatment with synthetic opioids. Plays a role in the regulation of salivation in response to synthetic opioids. May play a role in arousal and regulation of autonomic and neuroendocrine functions
- Specific Function
- dynorphin receptor activity
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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. [Article]
- 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. [Article]
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of steroid hormones and vitamins during embryogenesis (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:12865317, PubMed:14559847, PubMed:17178770, PubMed:9555064). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes 3beta-hydroxyandrost-5-en-17-one (dehydroepiandrosterone, DHEA), a precursor in the biosynthesis of androgen and estrogen steroid hormones (PubMed:17178770, PubMed:9555064). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1), particularly D-ring hydroxylated estrone at the C16-alpha position (PubMed:12865317, PubMed:14559847). Mainly hydroxylates all trans-retinoic acid (atRA) to 4-hydroxyretinoate and may play a role in atRA clearance during fetal development (PubMed:11093772). Also involved in the oxidative metabolism of xenobiotics including anticonvulsants (PubMed:9555064)
- Specific Function
- all-trans retinoic acid 18-hydroxylase activity
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57469.95 Da
References
- Flockhart Table of Drug Interactions [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- 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. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Functions as a 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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction
- Specific Function
- Not Available
Components:
References
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Translocates drugs and phospholipids across the membrane (PubMed:2897240, PubMed:35970996, PubMed:8898203, PubMed:9038218). Catalyzes the flop of phospholipids from the cytoplasmic to the exoplasmic leaflet of the apical membrane. Participates mainly to the flop of phosphatidylcholine, phosphatidylethanolamine, beta-D-glucosylceramides and sphingomyelins (PubMed:8898203). Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells (PubMed:2897240, PubMed:35970996, PubMed:9038218)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- ATP-dependent translocase ABCB1
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 29, 2024 14:47