Compound Detail

CHEMBL596

FENTANYL

💊 Approved Drug

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💊 Approved Drug

CCC(=O)N(c1ccccc1)C1CCN(CCc2ccccc2)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL596
Name	FENTANYL
Phase	Approved
Structure Type	MOL
InChI Key	PJMPHNIQZUBGLI-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

AD 923 AD-923 Breakyl Duragesic Duragesic-100 Duragesic-12 Duragesic-25 Duragesic-37 Duragesic-50 Duragesic-75 Durogesic Durogesic d-trans +18 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

336.5

MW (Da)

4.14

ALogP

HBA

HBD

23.6

PSA (Å²)

0.79

QED

Ro5 Violations

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 Natural Product

USAN Year

1963

Extended Properties

Molecular Formula	C22H28N2O
MW	336.48
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

Acute Pain Cancer Pain Cancer Pain Chronic Pain Neoplasms Neoplasms Pain Abscess Adenoma Aortic Coarctation Diabetic Neuropathies Liver Diseases Low Back Pain Lung Diseases Migraine Disorders Neoplasm Metastasis Obesity Obesity, Morbid Osteoarthritis Pancreatic Neoplasms

ATC Classification

N01AH01

fentanyl

Level 1: NERVOUS SYSTEM

Level 2: ANESTHETICS

N01AH51

fentanyl, combinations

Level 1: NERVOUS SYSTEM

Level 2: ANESTHETICS

N02AB03

fentanyl

Level 1: NERVOUS SYSTEM

Level 2: ANALGESICS

Drug Warnings

Black Box Warning

respiratory toxicity

Country: United States

Black Box Warning

misuse

Country: United States

Activity Summary

IC50 40 meas. best 8.94

Ki 37 meas. best 10.29

EC50 20 meas. best 9.68

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mu-type opioid receptor CHEMBL233	Ki	10.29	8.9875	0.1	8
Mu-type opioid receptor CHEMBL233	EC50	9.68	8.1627	0.2	11
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	9.41	9.41	0.4	1
Opioid receptor CHEMBL2094129	IC50	8.94	8.208	1.1	5
Mu-type opioid receptor CHEMBL270	IC50	8.91	7.405	1.2	2
Mu-type opioid receptor CHEMBL233	IC50	8.89	8.3733	1.3	3
Mu-type opioid receptor CHEMBL270	Ki	8.82	8.18	1.5	7
Cavia porcellus CHEMBL369	EC50	8.75	8.55	1.8	2
Opioid receptor CHEMBL2094129	Ki	8.67	8.67	2.2	1
Mu-type opioid receptor CHEMBL4354	IC50	8.51	8.4083	3.1	6
Cavia porcellus CHEMBL369	IC50	8.46	8.46	3.5	1
Delta-type opioid receptor CHEMBL3222	IC50	8.46	8.135	3.5	4
Mu-type opioid receptor CHEMBL2858	Ki	8.23	8.23	5.9	1
Mu-type opioid receptor CHEMBL4354	Ki	8.07	8.07	8.4	1
Mus musculus CHEMBL375	IC50	8.03	8.03	9.4	1
Mu-type opioid receptor CHEMBL270	EC50	7.49	7.49	32.4	1
Mu-type opioid receptor CHEMBL2858	EC50	6.88	6.88	133.0	1
Delta-type opioid receptor CHEMBL236	IC50	6.82	6.6625	150.0	4
Kappa-type opioid receptor CHEMBL3952	Ki	6.71	6.3967	196.5	3
Kappa-type opioid receptor CHEMBL237	Ki	6.71	6.71	196.5	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	IC50	6.45	6.45	354.0	1
Delta-type opioid receptor CHEMBL269	Ki	6.4	6.2133	400.0	3
Mus musculus CHEMBL375	EC50	6.31	6.31	490.0	1
D(4) dopamine receptor CHEMBL219	Ki	6.26	6.26	554.0	1
Delta-type opioid receptor CHEMBL3222	Ki	6.25	6.25	568.0	1
Delta-type opioid receptor CHEMBL236	Ki	6.24	6.1333	570.0	3
Kappa-type opioid receptor CHEMBL237	EC50	6.01	6.01	987.4	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	5.96	5.96	1100.0	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	5.85	5.85	1407.0	1
Kappa-type opioid receptor CHEMBL237	IC50	5.8	5.8	1580.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.74	5.74	1819.7	1
Sigma non-opioid intracellular receptor 1 CHEMBL4153	Ki	5.61	5.61	2474.3	1
Alpha-1A adrenergic receptor CHEMBL229	IC50	5.44	5.44	3660.0	1
Alpha-1B adrenergic receptor CHEMBL232	IC50	5.43	5.43	3690.0	1
Sigma non-opioid intracellular receptor 1 CHEMBL4153	IC50	5.3	5.3	4973.0	1
Monoamine oxidase CHEMBL2095205	Ki	5.26	5.26	5462.0	1
Kappa-type opioid receptor CHEMBL3952	IC50	5.23	5.23	5893.0	2
ATP-dependent translocase ABCB1 CHEMBL4302	IC50	5.19	5.19	6500.0	1
Histamine H1 receptor CHEMBL4701	IC50	4.7	4.7	19952.6	1
D(2) dopamine receptor CHEMBL217	Ki	4.68	4.68	21000.0	1
D(3) dopamine receptor CHEMBL234	Ki	4.58	4.58	26200.0	1
Nuclear receptor subfamily 1 group I member 2 CHEMBL3401	EC50	4.5	4.5	31600.0	3
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.34	4.34	46170.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	4.7	mL.min-1.kg-1	Homo sapiens
CL	39.0	mL.min-1.kg-1	Rattus norvegicus
CL	4.7	mL.min-1.kg-1	Homo sapiens
CL	13.0	mL.min-1.kg-1	Homo sapiens
CL	33.0	mL.min-1.kg-1	Macaca
CL	36.0	mL.min-1.kg-1	Canis lupus familiaris
CL	32.3	mL.min-1.g-1	Homo sapiens
CL	27.0	L/hr	Homo sapiens
CL	3.0	L/hr	Homo sapiens
CL	30.0	L/hr	Homo sapiens
Cmax	2.526	nM	Homo sapiens
Cmax	5.112	nM	Homo sapiens
Cmax	6.895	nM	Homo sapiens
Cmax	9.986	nM	Homo sapiens
Cmax	1.783	nM	Homo sapiens
Cmax	4.161	nM	Homo sapiens
Cmax	5.052	nM	Homo sapiens
Cmax	7.43	nM	Homo sapiens
Cmax	4.0	nM	Homo sapiens
Cmax	2.0	nM	Homo sapiens
Fu	0.16	-	-
Fu	0.016	-	-
Fu	0.16	-	Homo sapiens
Fu	0.16	-	Homo sapiens
MRT	3.2	hr	Homo sapiens
T1/2	3.0	hr	Homo sapiens
T1/2	0.65	hr	Mus musculus
T1/2	3.0	hr	Homo sapiens
T1/2	4.0	hr	Homo sapiens
Tmax	31.7	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mu-type opioid receptor	Ki	=	0.051	nM	10.29	Binding affinity to mu-opioid receptor (unknown origin) assessed as inhibition c...	37145921
Mu-type opioid receptor	Ki	=	0.083	nM	10.08	Binding affinity to MOR (unknown origin) assessed as inhibition constant	38156970
Mu-type opioid receptor	EC50	=	0.21	nM	9.68	Agonist activity at human MOR expressed in CHO-K1 cells assessed as decrease in ...	38810170
Sigma non-opioid intracellular receptor 1	Ki	=	0.39	nM	9.41	Inhibition of sigma 1 receptor (unknown origin)	32087465
Mu-type opioid receptor	EC50	=	0.51	nM	9.29	Agonist activity at human MOR expressed in CHO-K1 cells assessed as cAMP accumul...	31749912
Mu-type opioid receptor	Ki	=	1.1	nM	8.96	Binding affinity to mu opioid receptor (unknown origin) expressed in HEK cells a...	29400967
Opioid receptor	IC50	=	1.14	nM	8.94	Binding affinity to opioid receptors by the displacement of [3H]fentanyl in rat ...	6268786
Mu-type opioid receptor	IC50	=	1.23	nM	8.91	Displacement of [3H]DAMGO from rat brain mu opioid receptor incubated for 60 min...	31391893
Mu-type opioid receptor	IC50	=	1.3	nM	8.89	Binding affinity against mu-opiate receptor (human) using [3H]DAMGO radioligand	11585443
Mu-type opioid receptor	Ki	=	1.35	nM	8.87	Displacement of [3H]DAMGO from human mu opioid receptor measured after 2 hrs by ...	36206553
Mu-type opioid receptor	Ki	=	1.5	nM	8.82	Inhibition of [3H]DAMGO binding to mu opioid receptor of rat brain membranes	12570383
Opioid receptor	IC50	=	1.6	nM	8.8	Displacement [3H]naloxone from rat-brain Opioid receptors	6288945
Cavia porcellus	EC50	=	1.76	nM	8.75	Inhibition of electrically evoked contraction in guinea pig ileum determined in ...	2066993
Mu-type opioid receptor	EC50	=	1.9	nM	8.72	Agonist activity at mu-opioid receptor (unknown origin) expressed in CHO cells a...	38015878
Mu-type opioid receptor	EC50	=	1.9	nM	8.72	Agonist activity at mu-opioid receptor (unknown origin)	38015878
Mu-type opioid receptor	Ki	=	2.16	nM	8.67	Ability to displace [3H]naloxone from the Opioid receptor mu 1 isolated from the...	2170652
Opioid receptor	Ki	=	2.16	nM	8.67	In vitro affinity to displace [3H]naloxone from opiate receptor in freshly prepa...	2709383
Mu-type opioid receptor	Ki	=	2.16	nM	8.67	Displacement [3H]-naloxone from the Opioid receptor mu 1 isolated from rat brain...	2563773
Mu-type opioid receptor	Ki	=	2.9	nM	8.54	Displacement of [3H]DAMGO (2 nM ) from opioid receptor mu 1 in human brain	14698188
Mu-type opioid receptor	IC50	=	3.1	nM	8.51	Compound was tested in vitro for binding affinity towards mu opioid receptor by ...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.1007/s00044-012-0390-6	Mus musculus	28
16472241	10.2174/1570163043334794	Hepatotoxicity	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
33271020	10.1021/acs.jmedchem.0c01367	Mus musculus	12
38118143	10.1021/acs.jmedchem.3c01347	Mus musculus	12
27721146	10.1016/j.ejmech.2016.09.077	Mus musculus	9
2170652	10.1021/jm00172a032	Rattus norvegicus	9
37678143	10.1016/j.ejmech.2023.115783	Mus musculus	8
1847432	10.1021/jm00106a051	Rattus norvegicus	8
38810170	10.1021/acs.jmedchem.4c00333	Mu-type opioid receptor	8
15920768	10.1002/jps.20373	ADMET	8
2878076	10.1021/jm00161a027	Rattus norvegicus	7
20966043	10.1124/dmd.110.035105	Nuclear receptor subfamily 1 group I member 2	7
31597043	10.1021/acs.jmedchem.9b01301	ADMET	6
35961067	10.1016/j.ejmech.2022.114649	ADMET	6
12061889	10.1021/jm0200409	ADMET	5
6259354	10.1021/jm00133a017	Rattus norvegicus	5
2709383	10.1021/jm00125a008	Mus musculus	4
31391893	10.1039/C9MD00222G	Sigma non-opioid intracellular receptor 1	4
26706111	10.1016/j.bmc.2015.11.041	ADMET	4

Data from ChEMBL 36 via Core Engine