General
Preferred name
FENTANYL
Synonyms
FENTANYL HYDROCHLORIDE ()
FENTANYL CITRATE ()
Fentanyl hcl ()
Ionsys ()
Yemex ()
Sublimaze ()
Actiq ()
Fentalis Reservoir ()
Mezolar Matrix ()
Innovar ()
Fentanyl-12 ()
Fencino ()
Subsys ()
Fentanyl-100 ()
Sublimase ()
Opiodur ()
Tilofyl ()
Mylafent ()
Duragesic-25 ()
Recuvyra ()
Abstral- ()
AD 923 ()
Abstral ()
Fendrop ()
Osmanil ()
En3267 ()
Duragesic-37 ()
Fentanyl-62 ()
Victanyl ()
Duragesic-12 ()
Breakyl ()
N02AB03 ()
Recivit ()
Durogesic DTrans ()
Osmach ()
Pecfent ()
Fentanyl cii ()
Fentora ()
AD-923 ()
Effentora ()
Durogesic d-trans ()
IDS-NF-001 ()
Fentanyl-50 ()
Oralet ()
Fentanyl-37 ()
EN-3267 ()
Duragesic-100 ()
Fentanyl-25 ()
Phentanyl ()
R 4263 ()
Leptanal ()
Fentanest ()
Duragesic-75 ()
Durogesic ()
Matrifen ()
Fentanyl-75 ()
Duragesic-50 ()
Fentanyl-87 ()
Duragesic ()
Fentanyl ()
MCN-JR-4263-49 ()
Instanyl ()
Thalamonal ()
Kw-2246 ()
R-4263 ()
Fentanyl buccal ()
Fentanyl Citrate Preservative Free ()
Onsolis ()
Sublimaze Preservative Free ()
Fentanyl citrate cii ()
Lazanda ()
Fentanyl (hydrochloride) ()
Fentanyl-d5 (hydrochloride) ()
Fentanyl-d5 (hydrochloride) (CRM) ()
Fentanyl (citrate) ()
Fentanyl-13C6 (hydrochloride) ()
Fentanyl-13C6 (hydrochloride) (CRM) ()
P&D ID
PD009706
CAS
1443-54-5
437-38-7
990-73-8
2747915-16-6
2748624-58-8
Tags
drug
natural product
biased GPCR ligand
available
Approved by
PMDA
EMA
FDA
First approval
1968
2006
Drug Status
withdrawn
illicit
approved
vet_approved
investigational
Drug indication
Analgesic (narcotic)
Pain
Chronic pain
Cancer related pain
Analgesia
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCRIPTION
Fentanyl is a potent, addiction-forming narcotic analgesic. Marketed formulations contain the citrate salt (PubChem CID 13810).
ROE
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,L6598,L922]
HALF-LIFE
The half life of fentanyl is 7 hours.[L6601] The half life of fentanyl sublingual spray is 5-12 hours.[L6607]
PHARMACODYNAMICS
Fentanyl produces strong analgesia through its activation of opioid receptors.[Label,A179533] 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,L6598,L6601,L6604,L6607,L922,L6610,L6613]
MOA
Fentanyl binds to opioid receptors, especially the mu opioid receptor, which are coupled to G-proteins.[A179533] 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.[A179533] Reduced cAMP decreases cAMP dependant influx of calcium ions into the cell.[A179533] The exchange of GTP for GDP results in hyperpolarization of the cell and inhibition of nerve activity.[A179533]
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.[L6598,L6601,L6604,L6607,L922,L6610]
TOXICITY
Fentanyl has an intravenous LD50 of 2.91mg/kg in rats[A1220], 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,L6598,L6601,L6604,L6607,L922,L6610] 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,L6598,L6601,L6604,L6607,L922,L6610]
METABOLISM
Fentanyl is metabolized to a number of inactive metabolites.[A178639] Fentanyl is 99% N-dealkylated to norfentanyl by cytochrome P450.[A178639] It can also be amide hydrolyzed to despropionylfentanyl, or alkyl hydroxylated to hydroxyfentanyl which is N-dealkylated to hydroxynorfentanyl.[A178639]
DESCRIPTION
Fentanyl is a potent, synthetic, addiction-forming narcotic analgesic. Marketed formulations contain the citrate salt (PubChem CID 13810).
(GtoPdb)
ABSORPTION
Fentanyl sublingual tablets are 54% bioavailable[L6598], transmucosal lozenges are 50% bioavailable[L6601], buccal tablets are 65% bioavailable[L6604], sublingual spray is 76% bioavailable[L6607], and nasal spray is 20% more bioavailable than transmucosal[L6610] (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.[A179644] The AUC was 172±96ng\*min/mL for a 200µg dose and 1508±1360ng\*min/mL for a 1600µg dose.[A179644]; ; 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.[A179647] The AUC was 1.25±0.67ng\*h/mL for a 100µg dose and 10.38±3.70ng\*h/mL for a 800µg dose.[A179647]; ; 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.[A179653] The AUC was 0.42±0.35ng/mL\*h.[A179653]; ; Fentanyl nasal spray reaches a Cmax of 815±301pg/mL with a Tmax of less than 1 hour for a 200µg/100µL dose.[A179656] The AUC was 3772pg\*h/mL.[A179656]
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Cell lines
0
Organisms
2
Compound Sets
22
BiasDB
ChEMBL Approved Drugs
ChEMBL Drugs
Concise Guide to Pharmacology 2017/18
Concise Guide to Pharmacology 2019/20
Concise Guide to Pharmacology 2021/22
Concise Guide to Pharmacology 2023/24
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP
DrugMAP Approved Drugs
DrugMatrix
Guide to Pharmacology
Ki Database
LSP-MoA library (Laboratory of Systems Pharmacology)
NCATS Inxight Approved Drugs
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Withdrawn 2.0
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
90
Molecular Weight
336.22
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
0
Rotatable Bonds
6
Ring Count
3
Aromatic Ring Count
2
cLogP
4.14
TPSA
23.55
Fraction CSP3
0.41
Chiral centers
0.0
Largest ring
6.0
QED
0.79
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Member status
virtual
MOA
OPRM1 agonist
ATC
N02AB03
Therapeutic Class
Neurology Agents
Source data
