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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 Fentanyl-50 | ABSTRAL | SUBSYS | ACTIQ | FENTANYL HYDROCHLORIDE | Innovar | Fentanyl-12 | Duragesic-25 | Duragesic-12 | Sublimaze preservative free | ONSOLIS | LAZANDA | FENTORA | R-4263 | Sublimaze | Fentora | FENTANYL | Duragesic-100 | Fentanyl citrate preservative free | Fentanyl | SUBLIMAZE | Leptanal | Ionsys | Fentanyl-75 | Fentanyl-100 | IONSYS | MCN-JR-4263-49 | FENTANYL CITRATE | Oralet | Fentanyl-25 | Duragesic-75 | Duragesic-50 | DURAGESIC
Max Phase 4 (Approved)
Trade Names Fentanyl-50 | SUBSYS | Sublimaze | ACTIQ | Duragesic-12 | Duragesic-25 | Fentanyl-12 | FENTORA | LAZANDA | ONSOLIS | Sublimaze preservative free | Fentora | Duragesic-100 | Fentanyl | Fentanyl citrate preservative free | Fentanyl-100 | Fentanyl-75 | Leptanal | SUBLIMAZE | IONSYS | Fentanyl-25 | Oralet | DURAGESIC | Duragesic-50 | Duragesic-75 | ABSTRAL | Fentanyl citrate
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
ARTERIAL OCCLUSIVE DISEASESD001157HP:0005315OCCLUSIVE ARTERIAL DISEASE3ClinicalTrials
DYSPNEAD004417HP:0002094DYSPNEA0ClinicalTrials
OBESITY, MORBIDD009767EFO:0001074MORBID OBESITY3ClinicalTrials
OTITIS MEDIAD010033EFO:0004992OTITIS MEDIA2ClinicalTrials
ADENOMAD000236EFO:0000232ADENOMA3ClinicalTrials
PAIND010146EFO:0003843PAIN4ClinicalTrials
ATC
DailyMed
DailyMed
ClinicalTrials
SLEEP APNEA, OBSTRUCTIVED020181EFO:0003918OBSTRUCTIVE SLEEP APNEA3ClinicalTrials
SUBARACHNOID HEMORRHAGED013345EFO:0000713SUBARACHNOID HEMORRHAGE2ClinicalTrials
HYPOTENSIOND007022EFO:0005251HYPOTENSION2ClinicalTrials
IMMUNE SYSTEM DISEASESD007154EFO:0000540IMMUNE SYSTEM DISEASE1ClinicalTrials
NEOPLASMSD009369EFO:0000311CANCER4ClinicalTrials
ClinicalTrials
DailyMed
OPIOID-RELATED DISORDERSD009293EFO:0005611OPIOID DEPENDENCE1ClinicalTrials
BREAKTHROUGH PAIND0593904

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
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 1.000
CHEMBL287 Sigma opioid receptor Homo sapiens 0.999
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.999
CHEMBL236 Delta opioid receptor Homo sapiens 0.971
CHEMBL233 Mu opioid receptor Homo sapiens 0.954
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.921
CHEMBL240 HERG Homo sapiens 0.914
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.818
CHEMBL3198 Acetylcholinesterase Mus musculus 0.762
CHEMBL4641 Voltage-gated T-type calcium channel alpha-1G subunit Homo sapiens 0.582
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.559
CHEMBL1898 Serotonin 1b (5-HT1b) receptor Homo sapiens 0.485
CHEMBL3465 Sigma opioid receptor Mus musculus 0.423
CHEMBL228 Serotonin transporter Homo sapiens 0.416
CHEMBL4124 Histamine H3 receptor Rattus norvegicus 0.379
CHEMBL5857 Trace amine-associated receptor 1 Homo sapiens 0.311
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.234
CHEMBL264 Histamine H3 receptor Homo sapiens 0.228



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
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 1.000
CHEMBL236 Delta opioid receptor Homo sapiens 0.999
CHEMBL287 Sigma opioid receptor Homo sapiens 0.999
CHEMBL211 Muscarinic acetylcholine receptor M2 Homo sapiens 0.999
CHEMBL233 Mu opioid receptor Homo sapiens 0.969
CHEMBL3198 Acetylcholinesterase Mus musculus 0.903
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.856
CHEMBL240 HERG Homo sapiens 0.841
CHEMBL4354 Mu opioid receptor Cavia porcellus 0.710
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.691
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.662
CHEMBL344 Melanin-concentrating hormone receptor 1 Homo sapiens 0.612
CHEMBL1898 Serotonin 1b (5-HT1b) receptor Homo sapiens 0.594
CHEMBL4018 Neuropeptide Y receptor type 2 Homo sapiens 0.565
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.546
CHEMBL228 Serotonin transporter Homo sapiens 0.484
CHEMBL237 Kappa opioid receptor Homo sapiens 0.428
CHEMBL217 Dopamine D2 receptor Homo sapiens 0.324

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
336.5 336.2202 3.84 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 0.8

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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