Preferred name
FENTANYL
Synonyms
Ionsys ()
Fentanyl hcl ()
FENTANYL HYDROCHLORIDE ()
Tilofyl ()
Matrifen ()
Fentanyl-75 ()
Duragesic-50 ()
Sublimase ()
Duragesic-75 ()
Durogesic ()
Fentanyl-12 ()
R 4263 ()
Fentalis Reservoir ()
Victanyl ()
Fentanyl-25 ()
Fentanest ()
Oralet ()
En3267 ()
Fencino ()
Fentanyl-87 ()
Duragesic-12 ()
Effentora ()
Fentanyl-50 ()
Fentanilo ()
Fentanyl-100 ()
Mylafent ()
Fentora ()
Durogesic d-trans ()
Recuvyra ()
N02AB03 ()
Osmach ()
Recivit ()
Innovar ()
Osmanil ()
Duragesic-100 ()
Fentanyl cii ()
Phentanyl ()
Fentanyl-37 ()
Duragesic-37 ()
Opiodur ()
Subsys ()
Sublimaze ()
Pecfent ()
Mezolar Matrix ()
Actiq ()
Yemex ()
Breakyl ()
Abstral- ()
Fendrop ()
Leptanal ()
EN-3267 ()
Duragesic-25 ()
Durogesic DTrans ()
AD 923 ()
AD-923 ()
Fentanyl-62 ()
IDS-NF-001 ()
Abstral ()
Fentanyl ()
R-4263 ()
Onsolis ()
Sublimaze Preservative Free ()
Fentanyl buccal ()
Thalamonal ()
Fentanyl citrate cii ()
Kw-2246 ()
MCN-JR-4263-49 ()
Fentanyl Citrate Preservative Free ()
Lazanda ()
Instanyl ()
FENTANYL CITRATE ()
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
available
drug
biased GPCR ligand
Approved by
FDA
PMDA
EMA
First approval
2006
1968
Drug indication
Chronic pain
Cancer related pain
Analgesia
Analgesic (narcotic)
Pain
Drug Status
illicit
vet_approved
investigational
withdrawn
approved
Max Phase
4.0
Structure
SMILES
CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1
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
InChIkey
PJMPHNIQZUBGLI-UHFFFAOYSA-N
MOL
FENTANYL
RDKit 2D
25 27 0 0 0 0 0 0 0 0999 V2000
0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 -3.8971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1.5000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
-0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.0000 -2.5981 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
7.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
8.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 1 0
2 3 1 0
3 4 2 0
3 5 1 0
5 6 1 0
6 7 2 0
7 8 1 0
8 9 2 0
9 10 1 0
10 11 2 0
5 12 1 0
12 13 1 0
13 14 1 0
14 15 1 0
15 16 1 0
16 17 1 0
17 18 1 0
18 19 2 0
19 20 1 0
20 21 2 0
21 22 1 0
22 23 2 0
15 24 1 0
24 25 1 0
11 6 1 0
25 12 1 0
23 18 1 0
M END
> <ID>
PD009706
> <Name>
FENTANYL
(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]
22
9.2
8.12
OPRM1 Mu-type opioid receptor agonist
BIOCHEM 18.6x
CELL-BASED 851.1x
BIOCHEM 18.6x
CELL-BASED 851.1x
6
32
8.38
OPRD1,OPRK1,... Opioid receptor
0
5
7.93
SIGMAR1 Sigma non-opioid intracellular receptor 1
1
3
7.1
OPRK1 Kappa-type opioid receptor agonistpartial agonist
3
8
6.8
OPRD1 Delta-type opioid receptor agonist
3
15
6.35
OPRL1 Nociceptin receptor
2
1
6.26
DRD4 D(4) dopamine receptor
2
1
5.77
CHRM3 Muscarinic acetylcholine receptor M3
3
1
5.54
KCNH2 Voltage-gated inwardly rectifying potassium channel KCNH2
2
2
5.28
ADRA2B Alpha-2B adrenergic receptor
4
1
5.26
MAOA,MAOB Monoamine oxidase
0
1
5.19
ABCB1 ATP-dependent translocase ABCB1
4
1
5.11
CHRM1 Muscarinic acetylcholine receptor M1
2
1
5.1
GHSR Growth hormone secretagogue receptor type 1
2
1
4.68
DRD2 D(2) dopamine receptor
1
1
4.64
HRH1 Histamine H1 receptor
2
2
4.64
ADRA2C Alpha-2C adrenergic receptor
6
1
4.6
SLC6A3 Sodium-dependent dopamine transporter
4
1
4.58
DRD3 D(3) dopamine receptor
2
1
4.55
CHRNA4 Neuronal acetylcholine receptor subunit alpha-4
3
1
4.5
4.5
NR1I2 Nuclear receptor subfamily 1 group I member 2
2
1
4.34
SLC22A1 Solute carrier family 22 member 1
6
1
36
Abacavir transmembrane transport
SLC22A1
ABCB1
ABC-family proteins mediated transport
ABCB1
Acetylcholine regulates insulin secretion
CHRM3
Adrenaline signalling through Alpha-2 adrenergic receptor
ADRA2B
ADRA2C
Adrenaline,noradrenaline inhibits insulin secretion
ADRA2C
Adrenoceptors
ADRA2B
ADRA2C
Atorvastatin ADME
ABCB1
Ciprofloxacin ADME
SLC22A1
Defective SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)
SLC6A3
Defective SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS)
SLC6A3
Dopamine clearance from the synaptic cleft
SLC6A3
Dopamine receptors
DRD2
DRD3
DRD4
G alpha (i) signalling events
ADRA2B
DRD3
DRD4
OPRK1
OPRD1
OPRM1
ADRA2C
OPRL1
G alpha (q) signalling events
HRH1
CHRM3
CHRM1
GHSR
G alpha (z) signalling events
ADRA2B
ADRA2C
G-protein activation
OPRM1
Highly calcium permeable nicotinic acetylcholine receptors
CHRNA4
Highly calcium permeable postsynaptic nicotinic acetylcholine receptors
CHRNA4
Highly sodium permeable postsynaptic acetylcholine nicotinic receptors
CHRNA4
Histamine receptors
HRH1
Interleukin-4 and Interleukin-13 signaling
OPRD1
OPRM1
MECP2 regulates neuronal receptors and channels
OPRK1
OPRM1
Muscarinic acetylcholine receptors
CHRM3
CHRM1
Na+/Cl- dependent neurotransmitter transporters
SLC22A1
SLC6A3
Neurotransmitter clearance
SLC22A1
Norepinephrine Neurotransmitter Release Cycle
SLC22A1
Nuclear Receptor transcription pathway
NR1I2
Opioid Signalling
OPRM1
Organic cation transport
SLC22A1
Peptide ligand-binding receptors
OPRK1
OPRD1
OPRM1
GHSR
OPRL1
Phase 3 - rapid repolarisation
KCNH2
Potential therapeutics for SARS
SIGMAR1
Prednisone ADME
ABCB1
SUMOylation of intracellular receptors
NR1I2
Surfactant metabolism
ADRA2C
Voltage gated Potassium channels
KCNH2
48
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2022
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BiasDB (dataset)
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
92
GtoPdb 1626
ZINC ZINC000002522669
BindingDB 50008984
CCDC UGIYEP
ClinicalTrials.gov INSTANYL FENTORA ABSTRAL EFFENTORA FENTANYL CITRATE FENTANYL DURAGESIC FENTANYL BUCCAL R-4263 AD-923 FENTANYL HYDROC... LAZANDA ACTIQ AD 923 FENTANYL CII R 4263 N02AB03 SUBLIMAZE PECFENT IONSYS ONSOLIS EN-3267
COCONUT CNP0404596.0
DrugBank DB00813
DrugCentral 1164
IBM NIH D25A2962D3B78B7...
Nikkaji J5.736C
PDB 7V7
PharmGKB PA449599
(calculated by RDKit )
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
0
No structural alerts detected
(extracted from source data)
Member status
virtual
MOA
OPRM1 agonist
ATC
N02AB03
Therapeutic Class
Neurology Agents
