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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 Duragesic-25 | Fentanyl HCl | Fentanyl-100 | Duragesic-100 | MCN-JR-4263-49 | Fentanyl citrate | Sublimaze Preservative Free | Fentanyl Citrate Preservative Free | Duragesic-50 | Duragesic-75 | Actiq | Ionsys | Oralet | R-4263 | Subsys | Abstral | Fentora | Innovar | Lazanda | Onsolis | Fentanyl | Leptanal | Duragesic | Sublimaze | Fentanyl-12 | Fentanyl-25 | Fentanyl-50 | Fentanyl-75 | Duragesic-12
Max Phase 4 (Approved)
Trade Names Fentanyl Citrate Preservative Free | Sublimaze | Fentanyl-50 | Actiq | Onsolis | Sublimaze Preservative Free | Duragesic-12 | Duragesic-25 | Fentanyl-12 | Fentora | Abstral | Lazanda | Duragesic-100 | Fentanyl | Ionsys | Duragesic | Fentanyl-100 | Fentanyl-75 | Leptanal | Fentanyl Citrate | Fentanyl-25 | Oralet | Duragesic-50 | Duragesic-75 | Subsys
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

Mechanism of Action

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

Indications for CHEMBL596

MESH Heading MESH ID EFO ID EFO Term Max phase for indication
ADENOMAD000236EFO:0000232ADENOMA3
DYSPNEAD004417HP:0002094DYSPNEA0
NEOPLASMSD009369EFO:0000311CANCER4
OBESITY, MORBIDD009767EFO:0001074MORBID OBESITY3
OTITIS MEDIAD010033EFO:0004992OTITIS MEDIA3
PAIND010146EFO:0003843PAIN4
SLEEP APNEA, OBSTRUCTIVED020181EFO:0003918OBSTRUCTIVE SLEEP APNEA3
SUBARACHNOID HEMORRHAGED013345EFO:0000713SUBARACHNOID HEMORRHAGE2

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

Clinical Data

Number of clinical trials registered at clinicaltrials.gov
Number of reviews at The Cochrane Collaboration
Number of entries at British National Formulary

Structural Alerts

There are no structural alerts for CHEMBL596

Alternate Forms of Compound in ChEMBL


CHEMBL596

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 0.986
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.986
CHEMBL233 Mu opioid receptor Homo sapiens 0.961
CHEMBL236 Delta opioid receptor Homo sapiens 0.955
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.648
CHEMBL3198 Acetylcholinesterase Mus musculus 0.569
CHEMBL1898 Serotonin 1b (5-HT1b) receptor Homo sapiens 0.539
CHEMBL240 HERG Homo sapiens 0.490
CHEMBL4641 Voltage-gated T-type calcium channel alpha-1G subunit Homo sapiens 0.343
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.334



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 0.999
CHEMBL269 Delta opioid receptor Rattus norvegicus 0.991
CHEMBL287 Sigma opioid receptor Homo sapiens 0.990
CHEMBL233 Mu opioid receptor Homo sapiens 0.983
CHEMBL3198 Acetylcholinesterase Mus musculus 0.856
CHEMBL240 HERG Homo sapiens 0.762
CHEMBL1898 Serotonin 1b (5-HT1b) receptor Homo sapiens 0.727
CHEMBL237 Kappa opioid receptor Homo sapiens 0.687
CHEMBL245 Muscarinic acetylcholine receptor M3 Homo sapiens 0.590
CHEMBL4018 Neuropeptide Y receptor type 2 Homo sapiens 0.421
CHEMBL4302 P-glycoprotein 1 Homo sapiens 0.401
CHEMBL3602 Sigma opioid receptor Rattus norvegicus 0.389
CHEMBL1983 Serotonin 1d (5-HT1d) receptor Homo sapiens 0.385
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.271
CHEMBL3473 C-C chemokine receptor type 3 Homo sapiens 0.247

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

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
N01AH01 - fentanyl

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

ChemSpider ChemSpider:PJMPHNIQZUBGLI-UHFFFAOYSA-N
DailyMed fentanyl fentanyl citrate
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
eMolecules 901881
EPA CompTox Dashboard DTXSID9023049
FDA SRS UF599785JZ
Guide to Pharmacology 1626
Human Metabolome Database HMDB14951
IBM Patent System D25A2962D3B78B7521ADF1FC519A5C29
Nikkaji J5.736C
PharmGKB PA449599
PubChem 3345
PubChem: Thomson Pharma 14753493
SureChEMBL SCHEMBL8804

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