Compound Detail
CHEMBL16073
PHENACETIN 💊 Approved Drug
Enter ChEMBL ID:
Free Research Context
This compound will appear in recent viewed items on the research home for this browser.
Research home
View demo workspace
💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL16073 |
| Name | PHENACETIN |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | CPJSUEIXXCENMM-UHFFFAOYSA-N |
1
Targets
7
Activities
2
Assay Types
30
PK Parameters
20
Publications
11
Known Names
2
Indications
1
Mechanisms
Molecular Properties
179.2
MW (Da)
2.04
ALogP
2
HBA
1
HBD
38.3
PSA (Ų)
0.77
QED
0
Ro5 Violations
3
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| Availability | Withdrawn |
| Chirality | Achiral |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Unknown | - | - | ✓ | ✓ |
Indications
Fever Pain
ATC Classification
N02BE03
phenacetin
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02BE53
phenacetin, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02BE73
phenacetin, combinations with psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
Drug Warnings
Withdrawn
hematological toxicity
nephropathy; liver and kidney toxicity; carcinogenicity; haemolytic anaemia and methaemoglobinaemia
Withdrawn
nephrotoxicity
nephropathy; liver and kidney toxicity; carcinogenicity; haemolytic anaemia and methaemoglobinaemia
Withdrawn
nephrotoxicity
Nephropathy
Withdrawn
carcinogenicity
nephropathy; liver and kidney toxicity; carcinogenicity; haemolytic anaemia and methaemoglobinaemia
Withdrawn
carcinogenicity
renal damage and its carcinogenicity.
Withdrawn
hepatotoxicity
nephropathy; liver and kidney toxicity; carcinogenicity; haemolytic anaemia and methaemoglobinaemia
Withdrawn
hematological toxicity
high potential for harm to the kidneys and the possibility of hemolytic anemia and methemoglobinemia resulting from abuse
Withdrawn
hematological toxicity
high potential for harm to the kidneys and the possibility of hemolytic anemia and methemoglobinemia resulting from abuse
Withdrawn
nephrotoxicity
risk of nephropathy from long-term use
Withdrawn
hematological toxicity
nephropathy; liver and kidney toxicity; carcinogenicity; haemolytic anaemia and methaemoglobinaemia
Activity Summary
IC50 6 meas. best 8.31
Ki 1 meas.
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Cytochrome P450 1A2 CHEMBL3356 | IC50 | 8.31 | 7.84 | 4.9 | 5 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 19.2 | mL.min-1.kg-1 | Homo sapiens |
| CL | 21.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 24.55 | mL.min-1.g-1 | Homo sapiens |
| CL | 26.92 | uL.min-1.(10^6cells)-1 | Rattus norvegicus |
| CL | 933.0 | L/hr | Homo sapiens |
| CL | - | mL.min-1.g-1 | Mus musculus |
| CL | 0.4 | mL.min-1.g-1 | Mus musculus |
| CL | 0.1 | mL.min-1.g-1 | Mus musculus |
| CL | 1.3 | mL.min-1.g-1 | Mus musculus |
| CL | 0.1 | mL.min-1.g-1 | Rattus norvegicus |
| CL | 0.1 | mL.min-1.g-1 | Rattus norvegicus |
| CL | 0.1 | mL.min-1.g-1 | Rattus norvegicus |
| CL | 0.2 | mL.min-1.g-1 | Rattus norvegicus |
| CL | 0.4 | mL.min-1.g-1 | Homo sapiens |
| CL | 0.2 | mL.min-1.g-1 | Homo sapiens |
| CL | 4.0 | mL.min-1.g-1 | Homo sapiens |
| CL | 1.1 | mL.min-1.g-1 | Homo sapiens |
| CL | 615.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 8.94 | uL.min-1.(10^6cells)-1 | Homo sapiens |
| CL | 13.7 | uL.min-1.(10^6cells)-1 | Homo sapiens |
| CL | 19.6 | mL.min-1.kg-1 | Homo sapiens |
| CL | 0.0146 | mL.min-1.g-1 | Homo sapiens |
| CL | 0.0504 | mL.min-1.g-1 | Homo sapiens |
| CL | 0.0395 | mL.min-1.g-1 | Homo sapiens |
| CL | 23.6 | mL.min-1.kg-1 | Homo sapiens |
| CL | 1588.8 | mL.min-1.kg-1 | Mus musculus |
| Fu | 0.47 | - | Homo sapiens |
| Fu | 0.78 | - | Homo sapiens |
| Fu | 0.98 | - | Homo sapiens |
| Fu | 0.8 | - | Rattus norvegicus |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| Cytochrome P450 1A2 | IC50 | = | 4.9 | nM | 8.31 | Inhibition of CYP1A2 in human liver microsomes incubated for 15 to 40 mins in pr... | 35679690 |
| Cytochrome P450 1A2 | IC50 | = | 5.0 | nM | 8.3 | Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate mea... | 36577220 |
| Cytochrome P450 1A2 | IC50 | = | 12.0 | nM | 7.92 | Inhibition of CYP1A2 (unknown origin) | 38996652 |
| Cytochrome P450 1A2 | IC50 | = | 41.0 | nM | 7.39 | Inhibition of CYP1A2 (unknown origin) | 36442370 |
| Cytochrome P450 1A2 | IC50 | = | 52.4 | nM | 7.28 | Inhibition of CYP1A2 (unknown origin) | 35797898 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL3885861 | Rattus norvegicus | 1404 |
| - | 10.6019/CHEMBL3885881 | Rattus norvegicus | 301 |
| - | 10.5281/zenodo.13943903 | ADMET | 89 |
| 31158845 | 10.1038/s41586-019-1291-3 | ADMET | 68 |
| 22207054 | 10.1124/dmd.111.043067 | Arylacetamide deacetylase | 33 |
| 22331994 | 10.1124/dmd.111.044057 | Liver microsome | 11 |
| 15646539 | 10.1016/s0399-8320(04)95062-2 | Unchecked | 11 |
| 22331994 | 10.1124/dmd.111.044057 | Cytochrome P450 1A2 | 10 |
| 15646539 | 10.1016/s0399-8320(04)95062-2 | NON-PROTEIN TARGET | 8 |
| 22942316 | 10.1124/dmd.112.047373 | Liver microsome | 6 |
| 22207054 | 10.1124/dmd.111.043067 | ADMET | 6 |
| 33515864 | 10.1016/j.ejmech.2021.113174 | ADMET | 4 |
| 18426954 | 10.1124/dmd.108.020479 | ADMET | 4 |
| 37706660 | 10.1021/acs.jmedchem.3c00835 | ADMET | 4 |
| 21998403 | 10.1124/dmd.111.042309 | ADMET | 3 |
| 22942316 | 10.1124/dmd.112.047373 | Cytochrome P450 1A2 | 3 |
| 20014752 | 10.1021/tx900326k | Hepatotoxicity | 3 |
| - | 10.6019/CHEMBL3301361 | ADMET | 3 |
| 18834112 | 10.1021/jm800656v | Amine oxidase [flavin-containing] A | 2 |
| 22207054 | 10.1124/dmd.111.043067 | Liver microsome | 2 |
Data from ChEMBL 36 via Core Engine