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Compound Detail

CHEMBL688

FENTANYL CITRATE
💊 Approved Drug
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💊 Approved Drug
CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1.O=C(O)CC(O)(CC(=O)O)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL688
Name FENTANYL CITRATE
Phase Approved
Structure Type MOL
InChI Key IVLVTNPOHDFFCJ-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL596
Active Moiety CHEMBL596

Known Names

Abstral Actiq Effentora Fentanyl buccal Fentanyl citrate Fentanyl citrate cii Fentanyl citrate component of innovar Fentanyl citrate preservative free Fentora Instanyl Kw-2246 Lazanda +8 more
2
Targets
2
Activities
1
Assay Types
18
PK Parameters
9
Publications
20
Known Names
16
Indications
1
Mechanisms

Molecular Properties

336.5
MW (Da)
4.14
ALogP
2
HBA
0
HBD
23.6
PSA (Ų)
0.79
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1968
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning
USAN Year 1963

Extended Properties

Molecular Formula C28H36N2O8
MW 528.60
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -1.26

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mu opioid receptor agonist AGONIST Mu-type opioid receptor ✓ ✓

Indications

Breakthrough Pain Cancer Pain Cancer Pain Migraine Disorders Neoplasms Pain Chronic Pain Dyspnea Dyspnea Low Back Pain Lung Diseases, Interstitial Neuralgia Wounds and Injuries Pulmonary Disease, Chronic Obstructive Pulpitis Burns

Drug Warnings

Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
misuse
Country: United States

Activity Summary

IC50 2 meas. best 8.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL4354
 IC50 8.72 8.72 1.9 1
Delta-type opioid receptor
CHEMBL3222
 IC50 8.14 8.14 7.2 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1.7 ng.hr.mL-1 Homo sapiens
AUC 4.05 ng.hr.mL-1 Homo sapiens
AUC 9.55 ng.hr.mL-1 Homo sapiens
AUC 17.1 ng.hr.mL-1 Homo sapiens
Cmax 1.159 nM Homo sapiens
Cmax 2.229 nM Homo sapiens
Cmax 4.607 nM Homo sapiens
Cmax 7.46 nM Homo sapiens
PPB 80.0 % Homo sapiens
T1/2 3.217 hr Homo sapiens
T1/2 6.433 hr Homo sapiens
T1/2 6.35 hr Homo sapiens
T1/2 5.967 hr Homo sapiens
Tmax 0.6667 hr Homo sapiens
Tmax 0.4167 hr Homo sapiens
Tmax 0.4167 hr Homo sapiens
Tmax 0.3333 hr Homo sapiens
Vdss 4.0 L.kg-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor IC50 = 1.9 nM 8.72 Agonist activity at mu opioid receptor in Hartley guinea pig ileum/longitudinal ... 21925887
Delta-type opioid receptor IC50 = 7.2 nM 8.14 Agonist activity at delta opioid receptor in ICR mouse vas deferens assessed as ... 21925887

Literature References

PubMed DOI Target Context # Activities
25147603 10.1021/ml500117c Mus musculus 6
- 10.1007/s00044-012-0390-6 Mus musculus 3
11448232 10.1021/jm0100990 No relevant target 1
6481762 10.1021/jm00376a007 Mus musculus 1
6481762 10.1021/jm00376a007 No relevant target 1
21925887 10.1016/j.bmc.2011.08.027 Delta-type opioid receptor 1
21925887 10.1016/j.bmc.2011.08.027 Mu-type opioid receptor 1
513063 10.1021/jm00196a004 No relevant target 1
513063 10.1021/jm00196a004 Mus musculus 1

Data from ChEMBL 36 via Core Engine