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Atlas / Drug / Fentanyl

Fentanyl

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Also known as AD 923AD-923BreakylDuragesicDuragesic-100Duragesic-12Duragesic-25Duragesic-37Duragesic-50Duragesic-75DurogesicDurogesic d-transDurogesic dtransEN-3267En3267FencinoFendropFentalis reservoirFentanestFentanilo

Summary

Fentanyl (CHEMBL596) is an approved small-molecule opioid analgesic (ATC N02AB03) targeting OPRD1, OPRK1, and OPRM1; indicated across 38 conditions including neoplasm and adenoma.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N02AB03 (+2 more)
  • Targets: 3 (OPRD1, OPRK1, OPRM1)
  • Indications: 38 conditions
  • Clinical trials: 667
  • Chemistry: 336.5 Da · C22H28N2O

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL596
NameFentanyl
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID3345
ChEBICHEBI:119915
ATCN02AB03, N01AH01, N01AH51
Molecular formulaC22H28N2O
Molecular weight336.5
InChIKeyPJMPHNIQZUBGLI-UHFFFAOYSA-N

SMILES: CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3

IUPAC name: N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

ChEBI definition: A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.

Pharmacological roles (ChEBI): opioid analgesic, μ-opioid receptor agonist, anaesthesia adjuvant, intravenous anaesthetic, adjuvant, anaesthetic.

Also known as: AD 923, AD-923, Breakyl, Duragesic, Duragesic-100, Duragesic-12, Duragesic-25, Duragesic-37, Duragesic-50, Duragesic-75, Durogesic, Durogesic d-trans

Parent form; salt/anhydrous children: CHEMBL688, CHEMBL1201159

Patent coverage: 18,151 distinct patent families (71,460 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
OPRD1δ receptorFull agonist6.80.2%P41143
OPRK1κ receptorPartial agonist7.10%P41145
OPRM1μ receptorFull agonist9.20%P35372

Broader ChEMBL bioactivity targets: 31 (assay-derived). Sample: Neuronal acetylcholine receptor subunit alpha-4, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Opioid receptor, Monoamine oxidase, Muscarinic acetylcholine receptor M1, D(2) dopamine receptor, D(4) dopamine receptor, Alpha-1A adrenergic receptor, Histamine H1 receptor.

Bioactivity

ChEMBL activities: 95 potent at pChembl ≥ 5 of 106 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
OPRM110.29Ki0.05nMCHEMBL_ACT_25533880
OPRM110.08Ki0.08nMCHEMBL_ACT_25943332
OPRM19.68EC500.21nMCHEMBL_ACT_25868678
SIGMAR19.41Ki0.39nMCHEMBL_ACT_22958457
OPRM19.29EC500.51nMCHEMBL_ACT_19290676
OPRM18.96Ki1.1nMCHEMBL_ACT_19113895
OPRM18.96Ki1.1nMCHEMBL_ACT_29160757
P335338.94IC501.14nMCHEMBL_ACT_984704
P335358.91IC501.23nMCHEMBL_ACT_19128522
OPRM18.89IC501.3nMCHEMBL_ACT_117189
OPRM18.87Ki1.35nMCHEMBL_ACT_24967064
OPRM18.85Ki1.4nMCHEMBL_ACT_29160755
P335358.82Ki1.5nMCHEMBL_ACT_557720
P335338.8IC501.6nMCHEMBL_ACT_95000
OPRM18.72EC501.9nMCHEMBL_ACT_25674495
OPRM18.72EC501.9nMCHEMBL_ACT_25674648
OPRM18.7EC502nMCHEMBL_ACT_29160796
P335358.67Ki2.16nMCHEMBL_ACT_101807
P335338.67Ki2.16nMCHEMBL_ACT_310627
P335358.67Ki2.16nMCHEMBL_ACT_36529
OPRM18.55EC502.8nMCHEMBL_ACT_29160793
OPRM18.54Ki2.9nMCHEMBL_ACT_1119756
P972668.51IC503.1nMCHEMBL_ACT_1265137
P972668.51IC503.1nMCHEMBL_ACT_160171
OPRM18.48Ki3.3nMCHEMBL_ACT_24711734
P972668.47IC503.4nMCHEMBL_ACT_13331467
P972668.47IC503.4nMCHEMBL_ACT_15726948
P323008.46IC503.45nMCHEMBL_ACT_15702309
P972668.46IC503.45nMCHEMBL_ACT_3254404
P335358.4Ki3.97nMCHEMBL_ACT_820892

Target pathways

Aggregated over 3 target gene(s): OPRD1, OPRK1, OPRM1.

Top Reactome pathways

6 total, by targets touching each:

PathwayTargetsGenes
Peptide ligand-binding receptors3OPRD1, OPRK1, OPRM1
G alpha (i) signalling events3OPRD1, OPRK1, OPRM1
Interleukin-4 and Interleukin-13 signaling2OPRD1, OPRM1
MECP2 regulates neuronal receptors and channels2OPRK1, OPRM1
Opioid Signalling1OPRM1
G-protein activation1OPRM1

Dominant GO biological processes

GO termTargets
G protein-coupled receptor signaling pathway3
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway3
phospholipase C-activating G protein-coupled receptor signaling pathway3
neuropeptide signaling pathway3
G protein-coupled opioid receptor signaling pathway3
signal transduction3
immune response2
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger2
response to nicotine2
eating behavior2
response to ethanol2
sensory perception2
sensory perception of pain2
adult locomotory behavior1
negative regulation of gene expression1

Indications & clinical

Indications

38 indications (5 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
neoplasm4MONDO:0005070EFO:0000616
adenoma3MONDO:0004972EFO:0000232
morbid obesity3MONDO:0005139EFO:0001074
obstructive sleep apnea syndrome3MONDO:0007147EFO:0003918
obesity disorder3MONDO:0011122EFO:0001073
exocrine pancreatic carcinoma3MONDO:0005192EFO:0002618
liver disorder3MONDO:0005154EFO:0001421
abscess3MONDO:0005227EFO:0003030
respiratory failure3MONDO:0021113EFO:0009842
gastric neoplasm3MONDO:0021085MONDO:0001056
diabetic neuropathy3MONDO:0006626EFO:1000783
chronic kidney disease3MONDO:0005300EFO:0003884
aorta coarctation3MONDO:0007345EFO:1001267
osteoarthritis3MONDO:0005178MONDO:0005178
migraine disorder3MONDO:0005277MONDO:0005277
severe acute respiratory syndrome3MONDO:0005091MONDO:0100096
lung disorder3MONDO:0005275EFO:0003818
subarachnoid hemorrhage2MONDO:0005099EFO:0000713
bone fracture2MONDO:0005315EFO:0003931
hypotensive disorder2MONDO:0005468EFO:0005251
irritable bowel syndrome2MONDO:0005052EFO:0000555
hypospadias2MONDO:0005345EFO:0004209
pulpitis2MONDO:0006937EFO:1001139
scoliosis2MONDO:0005392EFO:0004273
delirium2MONDO:0045057EFO:0009267
breast neoplasm2MONDO:0021100MONDO:0007254
brain injury2MONDO:0043510MONDO:0043510
opiate dependence1MONDO:0005530EFO:0005611
acute respiratory distress syndrome1MONDO:0006502EFO:1000637
burn1MONDO:0043519EFO:0009516

8 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 667.

Phase distribution

PhaseTrials
Not specified248
PHASE4223
PHASE375
PHASE244
PHASE128
PHASE2/PHASE325
PHASE1/PHASE213
EARLY_PHASE111

Top trials by phase / activity

NCTPhaseStatusTitle
NCT03735563PHASE4RECRUITINGPremedication for Less Invasive Surfactant Administration
NCT05856136PHASE4RECRUITINGA Study to Investigate of the Effects of Opioid Exposure on the Ability of the Diaphragm Muscle
NCT06364540PHASE4RECRUITINGNebulized Ketamine to Nebulized Fentanyl for Treating Acute Painful Conditions in the ED
NCT06479655PHASE4RECRUITINGCompare the Efficacy and Outcome Between Fentanyl and Morphine as Analgo-sedation in Mechanically Ventilated Patients
NCT06498037PHASE4RECRUITINGOptimizing Subcutaneous FEntanyl titRation: RApid Achievement of Adequate Exposure When Treating Cancer-Related paIn.
NCT06576830PHASE4RECRUITINGOptimization of Pediatric Tonsillectomy to IMprove AnaLgesia
NCT06636578PHASE4RECRUITINGDexmedetomidine Ropivacaine Versus Plain Ropivacaine in Bilateral Pectoralis Nerve (PECS) Block
NCT06685705PHASE4NOT_YET_RECRUITINGComparative Study Between Intrathecal Magnesium Sulfate, Neostigmine and Fentanyl as Adjuvant for Bubivacaine in Postoperative Analgesia in Lower Abdominal Surgeries
NCT06696586PHASE4NOT_YET_RECRUITINGComparison Between Effect of Systemic Fentanyl Infusion and Fentanyl Added as An Adjuvant to Lidocaine in Bier Block For Controlling Pain in Patients Undergoing Hand Surgeries
NCT06704139PHASE4NOT_YET_RECRUITINGRole of Prophylactic Antiemetics in Women Receiving Intrathecal Morphine and Lipophilic Opioids Added to Bupivacaine for Cesarean Section
NCT06720506PHASE4NOT_YET_RECRUITINGComparsion Between Intrathecal Fentanyl and Intravenous Nalbuphine as a Postoperative Analgesia in Lower Limb Surgeries
NCT06722963PHASE4NOT_YET_RECRUITINGComparison of the Efficacy of Intraperitoneal Instillation of Fentanyl Versus Nalbuphine as Adjuvants to Bupivacaine for Postoperative Pain Relief in Patients Undergoing Laparoscopic Cholecystectomy
NCT06752629PHASE4NOT_YET_RECRUITINGComparison Between Dexmedetomidine and Fentanyl As an Adjuvant to Bupivacaine in the Paravertebral Nerve Block in Laparoscopic Cholecystectomy for Postoperative Analgesia: Randomized Comparative Clinical Trial.
NCT06763705PHASE4RECRUITINGComparison of Safety and Efficacy for Different Sedation Regimens During Colonoscopy
NCT06823349PHASE4RECRUITINGComparative Analysis of Analgesic Efficacy: by Single Shot Intrathecal Analgesia (SSSA) in Normal Labor
NCT06868589PHASE4ACTIVE_NOT_RECRUITINGReducing Pain With Methadone and Ketamine in Liver Transplant
NCT06962306PHASE4RECRUITINGOptimizing Perioperative Analgesia to Lower Pain Following Cleft Palate Surgery
NCT07078201PHASE4RECRUITINGComparative Analysis of Intraoperative Effect Dexmedetomidine and Fentanyl as an Adjuvant to Heavy Bupivacaine in Spinal Anaesthesia in Lower Limb Orthopedic Surgeries to Evaluate the Hemodynamic Stability and Onset and Duration of Motor Block of Using Intrathecal Dexmedetomidine and Fentanyl
NCT07091123PHASE4RECRUITINGPatient Preference and Long-term Outcomes in Persistent Spinal Pain Syndrome: A Prospective Study Comparing Spinal Cord Stimulation to Intrathecal Drug Delivery.
NCT07214714PHASE4NOT_YET_RECRUITINGHemodynamic and Cardiac Effects of Dexmedetomidine Versus Fentanyl by Intravenous Infusion as Adjuncts to General Anesthesia in Patients Undergoing Major Abdominal Cancer Surgeries.
NCT07276906PHASE4NOT_YET_RECRUITINGComparing Intramuscular Fentanyl and Ketorolac With Nerve of Arnold (NOA) Block for Bilateral Myringotomy
NCT07322419PHASE4RECRUITINGHemodynamics During Cesarean Delivery Under Spinal Anesthesia With Norepinephrine Versus Ephedrine
NCT07389096PHASE4RECRUITINGOpioid-Free Anesthesia Versus Opioid Based Anesthesia For Adolescent Idiopathic Scoliosis
NCT07435337PHASE4RECRUITINGEffect of Nalbuphine Versus Fentanyl on Hemdoynamic Effects of Laryngoscopy
NCT07496593PHASE4ACTIVE_NOT_RECRUITINGTotal Intravenous and Balanced Anesthesia in Diabetic Patients Undergoing Video-Assisted Thoracoscopy
NCT07556523PHASE4RECRUITINGPatient Quality of Recovery After TAVR With Different Sedation Regimens
NCT00027014PHASE4COMPLETEDHerb-Opioid Interactions
NCT00115102PHASE4COMPLETEDSensory Examination and Pharmacological Modulation of Oral Hyperexcitability in Patients With Atypical Odontalgia and Matched Healthy Controls
NCT00158873PHASE4COMPLETEDPharmaco-Economic Study Of Ultiva In Intensive Care Unit(ICU)Subjects
NCT00236327PHASE4TERMINATEDEvaluation of the Efficacy and Safety of Fentanyl Delivered by Adhesive Skin Patch in Out-Patients With Chronic Cancer Pain
NCT00236366PHASE4COMPLETEDA Study of the Effect on Pain Control of Treatment With Fentanyl, Administered Through the Skin, Compared With Placebo in Patients With Osteoarthritis
NCT00237341PHASE4COMPLETEDDuragesic® (Fentanyl Transdermal System) Functionality Trial in Chronic Low Back Pain
NCT00333632PHASE4WITHDRAWNEffect of Dexmedetomidine Upon Sleep Postoperatively
NCT00369811PHASE4COMPLETEDOxycodone vs Fentanyl for Pain Treatment After Laparoscopic Cholecystectomy
NCT00376831PHASE4COMPLETEDThe Efficacy of Midazolam & Ketamine Versus Midazolam & Fentanyl for Sedation in Ambulatory Colonoscopies
NCT00446420PHASE4COMPLETEDCognitive Impairment Following Sedation for Colonoscopy With Propofol, Midazolam and Fentanyl Combinations
NCT00454259PHASE4COMPLETEDFentanyl Ultra Low Doses Effects on the Nociceptive Threshold
NCT00512395PHASE4COMPLETEDInfluence of Epidural Analgesia in Elective Laparoscopic Colorectal Resections
NCT00524160PHASE4COMPLETEDA Study of the Effect on Pain Control of Treatment With Fentanyl, Administered Through the Skin, in Patients With Rheumatoid Arthritis or Osteoarthritis
NCT00527332PHASE4COMPLETEDEffects of General Anesthesia and Spinal-Morphine Anesthesia on Recovery and Comfort After Benign Abdominal Hysterectomy

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

GuidelineSourceGene(s)DosingRecommendation
Annotation of CPIC Guideline for alfentanil, buprenorphine, codeine, fCPICCOMT;OPRM1

PharmGKB also curates 48 clinical and 252 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

612 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DihydroergotamineChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
PROPOXYPHENEChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
TAFAMIDISChEMBL + PubChemPhase 4 (approved)OPRD1, OPRK1, OPRM1
ALVIMOPANChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMIODARONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMLODIPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
AMOXAPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ASTEMIZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BENZTROPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BUPRENORPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
BUTORPHANOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CANNABIDIOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CHLORPROMAZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CINNARIZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CLOTRIMAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
CODEINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ECONAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FLUPHENAZINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
FLUSPIRILENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
HYDROCODONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
HYDROMORPHONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LANSOPRAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LEVORPHANOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LOPERAMIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
LOXAPINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MEPERIDINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
METHADONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
METHYLNALTREXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MICONAZOLEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
MORPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NAFTOPIDILChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALBUPHINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALFURAFINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALMEFENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALOXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NALTREXONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
NELFINAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OLICERIDINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OXYCODONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
OXYMORPHONEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PAROXETINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PASIREOTIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PENTAZOCINEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
PIMOZIDEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
RALOXIFENEChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
RITONAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SAMIDORPHANChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SAQUINAVIRChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
SUNITINIBChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
TAMOXIFENChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
TRAMADOLChEMBLPhase 4 (approved)OPRD1, OPRK1, OPRM1
ASIMADOLINEChEMBLPhase 3OPRD1, OPRK1, OPRM1
ATICAPRANTChEMBLPhase 3OPRD1, OPRK1, OPRM1
CEBRANOPADOLChEMBLPhase 3OPRD1, OPRK1, OPRM1
NAVACAPRANTChEMBLPhase 3OPRD1, OPRK1, OPRM1
TRIMEBUTINEChEMBLPhase 3OPRD1, OPRK1, OPRM1
BREMAZOCINEChEMBLPhase 2OPRD1, OPRK1, OPRM1
CARFENTANILChEMBLPhase 2OPRD1, OPRK1, OPRM1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot