ACETAMINOPHEN

Search structure
Trade Names:
Synonyms:
Status: Approved (1968)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
UNII: 362O9ITL9D

Structure
InChI Key RZVAJINKPMORJF-UHFFFAOYSA-N
Smile CC(=O)Nc1ccc(O)cc1
InChI
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)

Physicochemical Descriptors

Property Name Value
Molecular Formula C8H9NO2
Molecular Weight 151.16
AlogP 1.35
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 1.0
Polar Surface Area 49.33
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 11.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 0.46 - EXP
pKa Dissociation Constant 9.38 - EXP
Henry's Law Constant 6.42E-13 atm-m3/mole EST
Atmospheric OH Rate Constant 1.77E-11 cm3/molecule-sec EST
Melting Point 170 deg C EXP
Water Solubility 1.40E+04 mg/L EXP
Vapor Pressure 7.00E-06 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Anandamide amidohydrolase inhibitor Wikipedia PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A1
- - 19100 - -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2E Cytochrome P450 2E1
- - - - 50
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 50
Enzyme Hydrolase
- 300000 - 245000 20-34
Enzyme Lyase
- - - 10000-10000 -
Enzyme Oxidoreductase
- 141000-141253.75 - - 8
Enzyme Transferase
- - - - 16.03
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -27.16--2.28
Epigenetic regulator Reader Bromodomain
- - 250000-250000 - 12
Other cytosolic protein
- 44000 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 96.68
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - 2099000
Unclassified protein
- 2300 - - -

Metabolites

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Indications

Mesh Heading Maximum Phase Mesh ID Reference
Dysmenorrhea 4 D004412 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Chronic Pain 3 D059350 ClinicalTrials
Respiratory Tract Infections 3 D012141 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Malaria 3 D008288 ClinicalTrials
Pemphigus 3 D010392 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Hypospadias 3 D007021 ClinicalTrials
Lupus Erythematosus, Systemic 3 D008180 ClinicalTrials
Kidney Diseases 3 D007674 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Abdominal Pain 3 D015746 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Lupus Nephritis 3 D008181 ClinicalTrials
Meningitis, Bacterial 3 D016920 ClinicalTrials
Streptococcal Infections 3 D013290 ClinicalTrials
Obesity 3 D009765 ClinicalTrials
Paget Disease, Extramammary 3 D010145 ClinicalTrials
Diabetic Neuropathies 3 D003929 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Myopia 3 D009216 ClinicalTrials
Sepsis 3 D018805 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Osteoarthritis, Hip 3 D015207 ClinicalTrials
Osteoarthritis 3 D010003 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Nausea 3 D009325 ClinicalTrials
Kidney Calculi 3 D007669 ClinicalTrials
Scoliosis 3 D012600 ClinicalTrials
Vomiting 3 D014839 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Ductus Arteriosus, Patent 3 D004374 ClinicalTrials
Immunoglobulin G4-Related Disease 2 D000077733 ClinicalTrials
Cleft Palate 2 D002972 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Fractures, Bone 2 D050723 ClinicalTrials
Pulpitis 2 D011671 ClinicalTrials
Diabetes Mellitus, Type 1 2 D003922 ClinicalTrials
Renal Colic 2 D056844 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Leukemia, Mast-Cell 2 D007946 ClinicalTrials
Sinusitis 2 D012852 ClinicalTrials
Mucositis 2 D052016 ClinicalTrials
Borderline Personality Disorder 2 D001883 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Pre-Eclampsia 2 D011225 ClinicalTrials
Hypertrophy 2 D006984 ClinicalTrials
Rotator Cuff Injuries 2 D000070636 ClinicalTrials
Tonsillitis 2 D014069 ClinicalTrials
Neck Pain 2 D019547 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Leukemia, T-Cell 2 D015458 ClinicalTrials
Digestive System Diseases 2 D004066 ClinicalTrials
Tension-Type Headache 2 D018781 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Brain Injuries 2 D001930 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 2 D054218 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Anxiety 2 D001007 ClinicalTrials
Hepatitis B, Chronic 1 D019694 ClinicalTrials
Intervertebral Disc Degeneration 1 D055959 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 1 D015464 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Anemia, Hemolytic, Autoimmune 1 D000744 ClinicalTrials
Pruritus 1 D011537 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Glycogen Storage Disease Type II 1 D006009 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Obesity, Morbid 1 D009767 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Nervous System Diseases 1 D009422 ClinicalTrials
Arrhythmias, Cardiac 1 D001145 ClinicalTrials
Parkinson Disease 1 D010300 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 1 D016553 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Immune System Diseases 1 D007154 ClinicalTrials
Tooth Diseases 0 D014076 ClinicalTrials
Glaucoma 0 D005901 ClinicalTrials
Ankle Fractures 0 D064386 ClinicalTrials
Brain Concussion 0 D001924 ClinicalTrials
Delirium 0 D003693 ClinicalTrials

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Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Injection site pain 14.7
General disorders and administration site conditions Injection site reaction 14.7
Investigations Body temperature increased
Gastrointestinal disorders Constipation
Gastrointestinal disorders Nausea 10.0
Nervous system disorders Headache 9.7
Nervous system disorders Nervous system disorder 9.7
Gastrointestinal disorders Nausea
Nervous system disorders Headache
Nervous system disorders Nervous system disorder
Nervous system disorders Insomnia 7.46
Psychiatric disorders Mental disorder 7.46
Blood and lymphatic system disorders Anaemia
Gastrointestinal disorders Constipation 6.7
Investigations Body temperature increased
Nervous system disorders Insomnia
Psychiatric disorders Mental disorder
Investigations Body temperature increased 5.47
Gastrointestinal disorders Vomiting 5.26
Nervous system disorders Headache
Skin and subcutaneous tissue disorders Pruritus
Gastrointestinal disorders Vomiting 4.0
Skin and subcutaneous tissue disorders Pruritus 3.3
Respiratory, thoracic and mediastinal disorders Alveolitis
Cardiac disorders Dizziness
Gastrointestinal disorders Vomiting
Blood and lymphatic system disorders Anaemia 2.7
Cardiac disorders Dizziness 2.7
General disorders and administration site conditions Injection site reaction 2.67
Gastrointestinal disorders Abdominal distension 2.0
Respiratory, thoracic and mediastinal disorders Cough 2.0
Gastrointestinal disorders Gastrointestinal disorder 2.0
General disorders and administration site conditions Injection site pain 2.0
Injury, poisoning and procedural complications Post procedural haemorrhage 2.0
Nervous system disorders Insomnia
General disorders and administration site conditions Asthenia 1.59
General disorders and administration site conditions Fatigue 1.59
Cardiac disorders Chest pain 1.33
Respiratory, thoracic and mediastinal disorders Alveolitis 1.3
Gastrointestinal disorders Diarrhoea 1.3
Gastrointestinal disorders Dyspepsia 1.3
Nervous system disorders Headache 1.3
Endocrine disorders Hyperglycaemia 1.3
Metabolism and nutrition disorders Hypokalaemia 1.3
Investigations Body temperature increased 1.05
Musculoskeletal and connective tissue disorders Hypotonia 1.05
Surgical and medical procedures Muscle relaxant therapy 1.05
Gastrointestinal disorders Nausea 1.05

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
27.64
General disorders and administration site conditions
12.75
Gastrointestinal disorders
6.79
Nervous system disorders
6.43
Hepatobiliary disorders
5.61
Psychiatric disorders
5.44
Investigations
4.38
Vascular disorders
4.12
Skin and subcutaneous tissue disorders
3.73
Respiratory, thoracic and mediastinal disorders
3.5
Immune system disorders
3.06
Cardiac disorders
2.55
Metabolism and nutrition disorders
2.09
Product issues
2.01

Cross References

Resources Reference
CAS NUMBER 103-90-2
ChEBI 46195
ChEMBL CHEMBL112
DrugBank DB00316
DrugCentral 52
EPA CompTox DTXSID2020006
FDA SRS 362O9ITL9D
Human Metabolome Database HMDB0001859
Guide to Pharmacology 5239
KEGG C06804
PDB TYL
PharmGKB PA448015
PubChem 1983
SureChEMBL SCHEMBL3480
ZINC ZINC000013550868
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