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Compound Detail

CHEMBL112

ACETAMINOPHEN
💊 Approved Drug
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💊 Approved Drug
CC(=O)Nc1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL112
Name ACETAMINOPHEN
Phase Approved
Structure Type MOL
InChI Key RZVAJINKPMORJF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Abdine Acephen Acetaminophen Acetaminophen component of allay Acetaminophen component of anexsia Acetaminophen component of anoquan Acetaminophen component of apadaz Acetaminophen component of bancap Acetaminophen component of bancap hc Acetaminophen component of bucet Acetaminophen component of butapap Acetaminophen component of co-gesic +18 more
18
Targets
40
Activities
4
Assay Types
30
PK Parameters
20
Publications
30
Known Names
20
Indications
3
Mechanisms

Molecular Properties

151.2
MW (Da)
1.35
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.60
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1968
Availability OTC
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Black Box Warning

Extended Properties

Molecular Formula C8H9NO2
MW 151.16
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness -0.64

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cyclooxygenase inhibitor INHIBITOR Cyclooxygenase ✓ ✓
Anandamide amidohydrolase inhibitor INHIBITOR Fatty-acid amide hydrolase 1 ✓ ✓
Vanilloid receptor opener OPENER Transient receptor potential cation channel subfamily V member 1 ✓ ✓

Indications

Acute Pain Arthritis Back Pain Common Cold Dysmenorrhea Fever Headache Influenza, Human Migraine Disorders Muscle Cramp Pain Pharyngitis Toothache Abdominal Pain Cancer Pain Chronic Pain Delirium Diabetic Neuropathies Ductus Arteriosus, Patent Hemorrhage

ATC Classification

N02BE01
paracetamol
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02BE51
paracetamol, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02BE71
paracetamol, combinations with psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Drug Warnings

Black Box Warning
misuse
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
nephrotoxicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States

Activity Summary

Ki 22 meas. best 5.6
IC50 12 meas. best 5.64
Kd 5 meas. best 5.24
EC50 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Myoglobin
CHEMBL2406892
 IC50 5.64 5.64 2300.0 1
Unchecked
CHEMBL612545
 Ki 5.6 5.6 2500.0 1
Carbonic anhydrase 12
CHEMBL3242
 Ki 5.39 5.39 4100.0 1
Unchecked
CHEMBL612545
 Kd 5.24 5.21 5790.0 2
Carbonic anhydrase 2
CHEMBL205
 Ki 5.21 5.21 6200.0 3
Unchecked
CHEMBL612545
 IC50 5.19 5.19 6520.0 1
Carbonic anhydrase 3
CHEMBL2885
 Ki 5.15 5.15 7100.0 1
Carbonic anhydrase 7
CHEMBL2326
 Ki 5.04 5.04 9100.0 1
Carbonic anhydrase 15
CHEMBL5973
 Ki 5.04 5.04 9230.0 1
Carbonic anhydrase 1
CHEMBL261
 Ki 5.0 5.0 10000.0 3
Carbonic anhydrase 14
CHEMBL3510
 Ki 4.97 4.97 10600.0 1
Carbonic anhydrase 4
CHEMBL3729
 Ki 4.94 4.94 11400.0 1
Cytochrome P450 1A1
CHEMBL2231
 Kd 4.72 4.72 19100.0 1
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL4358
 IC50 4.55 4.55 28380.0 1
Carbonic anhydrase 13
CHEMBL2186
 Ki 4.52 4.52 30300.0 1
Blood
CHEMBL613416
 IC50 4.36 4.195 44000.0 2
Arachidonate 5-lipoxygenase-activating protein
CHEMBL4550
 IC50 4.36 4.36 44000.0 1
Carbonic anhydrase 9
CHEMBL3594
 Ki 4.15 4.15 70700.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.06 4.06 86700.0 1
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 3.6 3.6 250000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 77800.0 ng.hr.mL-1 Homo sapiens
AUC 3700.0 ng.hr.mL-1 Homo sapiens
AUC 66000.0 ng.hr.mL-1 Homo sapiens
AUC 21000.0 ng.hr.mL-1 Homo sapiens
AUC 28000.0 ng.hr.mL-1 Homo sapiens
AUC 36700.0 ng.hr.mL-1 Homo sapiens
CL 4.0 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 4.9 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 5.0 mL.min-1.kg-1 Homo sapiens
CL 3.0 mL.min-1.g-1 Homo sapiens
CL 6.31 uL.min-1.(10^6cells)-1 Homo sapiens
CL 10.8 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 0.000198 mL.min-1.g-1 Homo sapiens
CL - - Homo sapiens
CL 0.198 uL/min Homo sapiens
CL 5.45 mL.min-1.kg-1 Homo sapiens
CL 380.0 ml/min Homo sapiens
CL 13.0 ml/min Homo sapiens
CL 12.2 mL.min-1.kg-1 Mus musculus
CL/F 365.0 mL/min Homo sapiens
Cmax 117094.47 nM Homo sapiens
Cmax 27785.13 nM Homo sapiens
F 79.0 % Homo sapiens
F 88.0 % Homo sapiens
F 85.0 % Homo sapiens
F 76.0 % Homo sapiens
F 75.0 % Homo sapiens
F 27.6 % Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Myoglobin IC50 = 2300.0 nM 5.64 Inhibition of myoglobin (unknown origin)-mediated arachidonic acid oxidation usi... 24482730
Unchecked Ki = 2500.0 nM 5.6 Inhibition of Malassezia globosa recombinant beta-carbonic anhydrase preincubate... 28343756
Carbonic anhydrase 12 Ki = 4100.0 nM 5.39 Inhibition of human carbonic anhydrase 12 catalytic domain by stopped-flow CO2 h... 18579385
Unchecked Kd = 5790.0 nM 5.24 Binding affinity to human CYP1A1-heme complex 20813430
Carbonic anhydrase 2 Ki = 6200.0 nM 5.21 Inhibition of human carbonic anhydrase 2 incubated for 15 mins prior to testing ... 26520662
Carbonic anhydrase 2 Ki = 6200.0 nM 5.21 Inhibition of human carbonic anhydrase 2 by stopped-flow CO2 hydration assay 18579385
Carbonic anhydrase 2 Ki = 6200.0 nM 5.21 Inhibition of human carbonic anhydrase 2 by stopped-flow CO2 hydrase assay 18501600
Unchecked IC50 = 6520.0 nM 5.19 Inhibition of soybean 15-LOX 37862815
Unchecked Kd = 6640.0 nM 5.18 Binding affinity to rat CYP2B1-heme complex 20813430
Carbonic anhydrase 3 Ki = 7100.0 nM 5.15 Inhibition of human carbonic anhydrase 3 by stopped-flow CO2 hydration assay 18579385
Carbonic anhydrase 7 Ki = 9100.0 nM 5.04 Inhibition of human carbonic anhydrase 7 by stopped-flow CO2 hydration assay 18579385
Carbonic anhydrase 15 Ki = 9230.0 nM 5.04 Inhibition of mouse recombinant carbonic anhydrase 15 by stopped-flow CO2 hydras... 18501600
Carbonic anhydrase 1 Ki = 10000.0 nM 5.0 Inhibition of human carbonic anhydrase 1 incubated for 15 mins prior to testing ... 26520662
Carbonic anhydrase 1 Ki = 10000.0 nM 5.0 Inhibition of human carbonic anhydrase 1 by stopped-flow CO2 hydration assay 18579385
Carbonic anhydrase 1 Ki = 10000.0 nM 5.0 Inhibition of human carbonic anhydrase 1 by stopped-flow CO2 hydrase assay 18501600
Carbonic anhydrase 14 Ki = 10600.0 nM 4.97 Inhibition of human carbonic anhydrase 14 by stopped-flow CO2 hydration assay 18579385
Carbonic anhydrase 4 Ki = 11400.0 nM 4.94 Inhibition of human carbonic anhydrase 4 by stopped-flow CO2 hydration assay 18579385
Cytochrome P450 1A1 Kd = 19100.0 nM 4.72 Binding affinity to human CYP1A1 20813430
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 28380.0 nM 4.55 DRUGMATRIX: Lipoxygenase 15-LO enzyme inhibition (substrate: Linoleic acid) -
Carbonic anhydrase 13 Ki = 30300.0 nM 4.52 Inhibition of mouse carbonic anhydrase 13 by stopped-flow CO2 hydration assay 18579385

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1404
- 10.6019/CHEMBL3885881 Rattus norvegicus 648
7002186 10.1111/j.1365-2125.1980.tb01812.x Homo sapiens 58
3746820 10.1021/jm00159a029 Mus musculus 43
- 10.1039/C5MD00551E No relevant target 28
17202677 10.1248/bpb.30.157 Homo sapiens 24
7452663 10.1021/jm00185a001 Rattus norvegicus 24
7328601 10.1021/jm00140a014 ADMET 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
7452663 10.1021/jm00185a001 Mus musculus 16
16919959 10.1016/j.bmc.2006.07.054 Mus musculus 15
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
32629335 10.1016/j.ejmech.2020.112600 ADMET 11
19327871 10.1016/j.ejmech.2009.02.026 Mus musculus 9
20070106 10.1021/jm901371v Homo sapiens 8
33257173 10.1016/j.ejmech.2020.113042 Unchecked 8
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 8
7002186 10.1111/j.1365-2125.1980.tb01812.x ADMET 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
7365746 10.1021/jm00177a019 ADMET 7

Data from ChEMBL 36 via Core Engine