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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL596
CHEMBL596
Compound Name FENTANYL
ChEMBL Synonyms Sublimaze | ABSTRAL | OSMANIL | OPIODUR | FENTANYL-87 | FENTANYL-12 | FENTALIS RESERVOIR | ACTIQ | THALAMONAL | FENTANYL HYDROCHLORIDE | LAZANDA | FENTORA | DURAGESIC-75 | DURAGESIC-50 | Innovar | FENTANYL-37 | FENCINO | SUBLIMAZE PRESERVATIVE FREE | ONSOLIS | SUBSYS | Fentora | FENTANYL | DUROGESIC DTRANS | R-4263 | FENTANYL CITRATE PRESERVATIVE FREE | PECFENT | OSMACH | MATRIFEN | BREAKYL | RECIVIT | FENTANYL-62 | FENTANYL-100 | TILOFYL | MEZOLAR MATRIX | Leptanal | IONSYS | FENTANYL-75 | FENTANYL-50 | FENTANYL-25 | DURAGESIC-12 | SUBLIMAZE | MCN-JR-4263-49 | FENTANYL CITRATE | Oralet | DUROGESIC | YEMEX | VICTANYL | MYLAFENT | EFFENTORA | DURAGESIC-25 | DURAGESIC-100 | DURAGESIC
Max Phase 4 (Approved)
Trade Names ACTIQ | THALAMONAL | FENTALIS RESERVOIR | FENTANYL-12 | FENTANYL-87 | OPIODUR | OSMANIL | SUBSYS | Sublimaze | FENTORA | LAZANDA | ONSOLIS | SUBLIMAZE PRESERVATIVE FREE | DURAGESIC-50 | DURAGESIC-75 | FENCINO | FENTANYL-37 | FENTANYL | DUROGESIC DTRANS | Fentora | FENTANYL CITRATE PRESERVATIVE FREE | BREAKYL | MATRIFEN | OSMACH | PECFENT | FENTANYL-100 | FENTANYL-62 | RECIVIT | IONSYS | SUBLIMAZE | DURAGESIC-12 | FENTANYL-25 | FENTANYL-50 | FENTANYL-75 | Leptanal | MEZOLAR MATRIX | TILOFYL | FENTANYL CITRATE | DUROGESIC | Oralet | ABSTRAL | DURAGESIC | DURAGESIC-100 | DURAGESIC-25 | EFFENTORA | MYLAFENT | VICTANYL | YEMEX
Molecular Formula C22H28N2O

Additional synonyms for CHEMBL596 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCC(=O)N(C1CCN(CCc2ccccc2)CC1)c3ccccc3
Standard InChI InChI=1S/C22H28N2O/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17- ...
Download InChI
Standard InChI Key PJMPHNIQZUBGLI-UHFFFAOYSA-N

Sources

  • British National Formulary
  • Curated Drug Pharmacokinetic Data
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL596

Molecule Features

CHEMBL596 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Mu opioid receptor agonist Mu opioid receptor DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
AdenomaD000236EFO:0000232adenoma3ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
DailyMed
ClinicalTrials
Sleep Apnea, ObstructiveD020181EFO:0003918obstructive sleep apnea3ClinicalTrials
DyspneaD0044170ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma3ClinicalTrials
AsthmaD001249EFO:0000270asthma2ClinicalTrials
HypospadiasD007021EFO:0004209hypospadias2ClinicalTrials
HypotensionD007022EFO:0005251hypotension2ClinicalTrials
Otitis MediaD010033EFO:0004992Otitis media2ClinicalTrials
PainD010146EFO:0003843pain4ATC
ClinicalTrials
DailyMed
ClinicalTrials
DailyMed
ClinicalTrials
PulpitisD011671EFO:1001139pulpitis2ClinicalTrials
ClinicalTrials
Breakthrough PainD0593904DailyMed
Opioid-Related DisordersD009293EFO:0005611opioid dependence1ClinicalTrials
Subarachnoid HemorrhageD013345EFO:0000713subarachnoid hemorrhage2ClinicalTrials
Idiopathic Pulmonary FibrosisD054990EFO:0000768idiopathic pulmonary fibrosis3ClinicalTrials
Arterial Occlusive DiseasesD0011573ClinicalTrials
Irritable Bowel SyndromeD043183EFO:0000555irritable bowel syndrome2ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma3ClinicalTrials
Wounds and InjuriesD014947EFO:0000546injury2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
Fractures, BoneD050723EFO:0003931bone fracture2ClinicalTrials
ObesityD009765EFO:0001073obesity3ClinicalTrials
Obesity, MorbidD009767EFO:0001074morbid obesity3ClinicalTrials
NeuralgiaD009437EFO:0005762neuropathic pain3ClinicalTrials

Clinical Data

ClinicalTrials.gov FENTANYL
The Cochrane Collaboration FENTANYL

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL596. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL270 Mu opioid receptor Rattus norvegicus 1.000
CHEMBL274 C-C chemokine receptor type 5 Homo sapiens 1.000
CHEMBL287 Sigma opioid receptor Homo sapiens 1.000
CHEMBL233 Mu opioid receptor Homo sapiens 0.989
CHEMBL236 Delta opioid receptor Homo sapiens 0.987
CHEMBL240 HERG Homo sapiens 0.987
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.982
CHEMBL3198 Acetylcholinesterase Mus musculus 0.853
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.847
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.832
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.812
CHEMBL3465 Sigma opioid receptor Mus musculus 0.802
CHEMBL264 Histamine H3 receptor Homo sapiens 0.756
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.752
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.581
CHEMBL2858 Mu opioid receptor Mus musculus 0.483
CHEMBL234 Dopamine D3 receptor Homo sapiens 0.476
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.397
CHEMBL5857 Trace amine-associated receptor 1 Homo sapiens 0.391
CHEMBL3473 C-C chemokine receptor type 3 Homo sapiens 0.359



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL270 Mu opioid receptor Rattus norvegicus 1.000
CHEMBL274 C-C chemokine receptor type 5 Homo sapiens 1.000
CHEMBL236 Delta opioid receptor Homo sapiens 1.000
CHEMBL287 Sigma opioid receptor Homo sapiens 1.000
CHEMBL233 Mu opioid receptor Homo sapiens 0.982
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.980
CHEMBL4018 Neuropeptide Y receptor type 2 Homo sapiens 0.961
CHEMBL4354 Mu opioid receptor Cavia porcellus 0.926
CHEMBL240 HERG Homo sapiens 0.922
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.911
CHEMBL3198 Acetylcholinesterase Mus musculus 0.903
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.880
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.832
CHEMBL234 Dopamine D3 receptor Homo sapiens 0.801
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.769
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.658
CHEMBL264 Histamine H3 receptor Homo sapiens 0.590
CHEMBL3465 Sigma opioid receptor Mus musculus 0.581
CHEMBL3473 C-C chemokine receptor type 3 Homo sapiens 0.517
CHEMBL1941 Histamine H2 receptor Homo sapiens 0.504

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
336.5 336.2202 4.14 6 23.55 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 0 0 3 0 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 8.92 3.68 2.61 2 25 0.79

Structural Alerts

There are no structural alerts for CHEMBL596

Compound Cross References

ATC N - NERVOUS SYSTEM
N02 - ANALGESICS
N02A - OPIOIDS
N02AB - Phenylpiperidine derivatives
N02AB03 - fentanyl

N - NERVOUS SYSTEM
N01 - ANESTHETICS
N01A - ANESTHETICS, GENERAL
N01AH - Opioid anesthetics
N01AH51 - fentanyl, combinations

N - NERVOUS SYSTEM
N01 - ANESTHETICS
N01A - ANESTHETICS, GENERAL
N01AH - Opioid anesthetics
N01AH01 - fentanyl

ChemSpider ChemSpider:PJMPHNIQZUBGLI-UHFFFAOYSA-N
DailyMed fentanyl fentanyl citrate fentanyl hydrochloride
PubChem SID: 144206164 SID: 50113065
Wikipedia Fentanyl

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL596



ACToR 437-38-7
BindingDB 50008984
ChEBI 119915
DrugBank DB00813
DrugCentral 1164
eMolecules 901881
EPA CompTox Dashboard DTXSID9023049
FDA SRS UF599785JZ
Guide to Pharmacology 1626
Human Metabolome Database HMDB0014951
IBM Patent System D25A2962D3B78B7521ADF1FC519A5C29
Nikkaji J5.736C
PDBe 7V7
PharmGKB PA449599
PubChem 3345
PubChem: Thomson Pharma 14753493
SureChEMBL SCHEMBL8804
ZINC ZINC000002522669

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/PJMPHNIQZUBGLI-UHFFFAOYSA-N spacer
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