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Compound Detail

CHEMBL658

SUFENTANIL
💊 Approved Drug
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💊 Approved Drug
CCC(=O)N(c1ccccc1)C1(COC)CCN(CCc2cccs2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL658
Name SUFENTANIL
Phase Approved
Structure Type MOL
InChI Key GGCSSNBKKAUURC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

IDS-NS-001 R 30,730 R-30730 Sufentanil Sufentanilo Sufentanyl
7
Targets
10
Activities
3
Assay Types
11
PK Parameters
20
Publications
6
Known Names
7
Indications

Molecular Properties

386.6
MW (Da)
4.21
ALogP
4
HBA
0
HBD
32.8
PSA (Ų)
0.68
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1984
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -fentanil
USAN Year 1976

Extended Properties

Molecular Formula C22H30N2O2S
MW 386.56
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -1.18

Indications

Back Pain Pain Pregnancy Wounds and Injuries Chronic Pain Pulpitis Delirium

ATC Classification

N01AH03
sufentanil
Level 1: NERVOUS SYSTEM
Level 2: ANESTHETICS

Activity Summary

IC50 5 meas. best 9.4
EC50 3 meas. best 8.89
Ki 2 meas. best 10.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Opioid receptor
CHEMBL2094129
 Ki 10.7 10.7 0.0 1
Mu-type opioid receptor
CHEMBL270
 Ki 9.66 9.66 0.2 1
Mu-type opioid receptor
CHEMBL270
 IC50 9.4 9.4 0.4 1
Mu-type opioid receptor
CHEMBL233
 EC50 8.89 8.855 1.3 2
Opioid receptor
CHEMBL2094129
 IC50 8.64 8.64 2.3 1
Cavia porcellus
CHEMBL369
 EC50 8.13 8.13 7.4 1
Sigma non-opioid intracellular receptor 1
CHEMBL4153
 IC50 5.68 5.68 2077.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.35 5.35 4500.0 1
Solute carrier family 22 member 1
CHEMBL5685
 IC50 4.71 4.71 19360.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 14.9 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
Cmax 0.7 nM Homo sapiens
Cmax 0.1 nM Homo sapiens
Fu 0.07 - Homo sapiens
Fu 0.075 - Homo sapiens
Fu 0.075 - Homo sapiens
MRT 10.0 hr Homo sapiens
T1/2 14.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Opioid receptor Ki = 0.02 nM 10.7 In vitro affinity to displace [3H]naloxone from opiate receptor in freshly prepa... 2709383
Mu-type opioid receptor Ki = 0.22 nM 9.66 Ability to displace [3H]naloxone from the Opioid receptor mu 1 isolated from the... 2170652
Mu-type opioid receptor IC50 = 0.4 nM 9.4 Displacement of [3H]DAMGO from rat brain mu opioid receptor incubated for 60 min... 31391893
Mu-type opioid receptor EC50 = 1.3 nM 8.89 Agonist activity at human mu opioid receptor expressed in CHO cell membranes aft... 29939744
Mu-type opioid receptor EC50 = 1.5 nM 8.82 Agonist activity at human mu opioid receptor expressed in human U2OS cells co-tr... 29939744
Opioid receptor IC50 = 2.3 nM 8.64 Displacement of [3H]nalotrexone from rat-brain Opioid receptors 6288945
Cavia porcellus EC50 = 7.43 nM 8.13 Inhibition of electrically evoked contraction in guinea pig ileum determined in ... 2066993
Sigma non-opioid intracellular receptor 1 IC50 = 2077.0 nM 5.68 Displacement of [3H]pentazocine from LAL/HA/BR guinea pig brain sigma1 receptor ... 31391893
ATP-dependent translocase ABCB1 IC50 = 4500.0 nM 5.35 TP_TRANSPORTER: inhibition of Digoxin transepithelial transport (basal to apical... 11964599
Solute carrier family 22 member 1 IC50 = 19360.0 nM 4.71 Inhibition of human OCT1 expressed in HEK293 cells assessed as reduction in ASP+... 31597043

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
31597043 10.1021/acs.jmedchem.9b01301 ADMET 6
29939744 10.1021/acs.jmedchem.8b00435 Mu-type opioid receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
31597043 10.1021/acs.jmedchem.9b01301 Unchecked 4
2709383 10.1021/jm00125a008 Mus musculus 4
31597043 10.1021/acs.jmedchem.9b01301 Solute carrier family 22 member 1 4
2066993 10.1021/jm00111a041 Rattus norvegicus 2
11964599 10.1097/00000542-200204000-00019 ATP-dependent translocase ABCB1 2
19445515 10.1021/jm900403j Homo sapiens 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
2878076 10.1021/jm00161a027 No relevant target 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
14971904 10.1021/jm030408h ADMET 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
2170652 10.1021/jm00172a032 Mus musculus 2
38781921 10.1016/j.ejmech.2024.116364 Mu-type opioid receptor 1

Data from ChEMBL 36 via Core Engine