paracetamol indications/contra

Stem definitionDrug idCAS RN
52 103-90-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • acetaminophen
  • acetaminofen
  • aminofen
  • panadol
  • paracetamol
  • neopap
Analgesic antipyretic derivative of acetanilide. It has weak anti-inflammatory properties and is used as a common analgesic, but may cause liver, blood cell, and kidney damage.
  • Molecular weight: 151.17
  • Formula: C8H9NO2
  • CLOGP: 0.49
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 2
  • TPSA: 49.33
  • ALOGS: -1.56
  • ROTB: 1

Drug dosage:

DoseUnitRoute
3 g O
3 g P
3 g R

Approvals:

DateAgencyCompanyOrphan
Nov. 7, 1968 FDA POLYMEDICA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Completed suicide 18417.75 26.03 4866 27523 26248 3327222
Toxicity to various agents 16078.34 26.03 4788 27601 42266 3311204
Overdose 13183.52 26.03 3829 28560 30149 3323321
Intentional overdose 7181.20 26.03 2011 30378 13214 3340256
Acute hepatic failure 5275.52 26.03 1212 31177 2911 3350559
Drug hypersensitivity 3544.06 26.03 1466 30923 34214 3319256
Suicide attempt 3297.58 26.03 1121 31268 14726 3338744
Intentional product misuse 3223.76 26.03 1044 31345 11657 3341813
Drug abuse 3221.50 26.03 1143 31246 17187 3336283
Cardio-respiratory arrest 2571.61 26.03 926 31463 14514 3338956
Death 2454.67 26.03 1887 30502 150437 3203033
Respiratory arrest 2435.95 26.03 823 31566 10545 3342925
Cardiac arrest 2421.12 26.03 1037 31352 26282 3327188
Accidental overdose 2260.18 26.03 695 31694 6423 3347047
Hepatic failure 2108.72 26.03 727 31662 9925 3343545
Vomiting 2077.30 26.03 1388 31001 88143 3265327
Hepatotoxicity 2047.53 26.03 608 31781 4923 3348547
Liver injury 1947.29 26.03 531 31858 3033 3350437
Metabolic acidosis 1881.16 26.03 636 31753 8142 3345328
Coma 1513.16 26.03 595 31794 11957 3341513
Alanine aminotransferase increased 1488.76 26.03 708 31681 22932 3330538
Hepatic necrosis 1460.03 26.03 365 32024 1382 3352088
Poisoning 1349.92 26.03 434 31955 4678 3348792
Hypotension 1332.85 26.03 845 31544 48669 3304801
Somnolence 1259.82 26.03 700 31689 31504 3321966
Aspartate aminotransferase increased 1251.88 26.03 607 31782 20506 3332964
Drug-induced liver injury 1128.02 26.03 379 32010 4734 3348736
Acute kidney injury 1074.32 26.03 740 31649 48943 3304527
Nausea 1071.13 26.03 1106 31283 128539 3224931
Transaminases increased 1069.02 26.03 392 31997 6432 3347038

Pharmacologic Action:

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SourceCodeDescription
ATC N02BE01 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Anilides
ATC N02AJ01 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02AJ06 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02AJ13 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02AJ17 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with non-opioid analgesics
ATC N02BE51 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Anilides
ATC N02BE71 NERVOUS SYSTEM
ANALGESICS
OTHER ANALGESICS AND ANTIPYRETICS
Anilides
CHEBI has role CHEBI:35481 non-narcotic analgesic
CHEBI has role CHEBI:35493 antipyretic
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D058633 Antipyretics
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Sinus headache indication 4969004
Pain indication 22253000
Toothache indication 27355003
Migraine indication 37796009 DOID:6364
Joint pain indication 57676002
Allergic rhinitis indication 61582004
Common cold indication 82272006 DOID:10459
Backache indication 161891005
Headache disorder indication 230461009
Influenza-like symptoms indication 315642008
Fever indication 386661006
Tension-type headache indication 398057008
Arthritic Pain indication
Pain Treatment Adjunct indication
Hepatic encephalopathy contraindication 13920009 DOID:13413
Cirrhosis of liver contraindication 19943007 DOID:5082
Hepatic failure contraindication 59927004
Disease of liver contraindication 235856003 DOID:409
Vascular headache off-label use 128187005
Fibromyalgia off-label use 203082005 DOID:631

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.69 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
325MG XARTEMIS XR MALLINCKRODT INC N204031 March 11, 2014 DISCN TABLET, EXTENDED RELEASE ORAL 7976870 June 1, 2027 METHOD OF TREATING PATIENTS WITH GASTRIC RETENTIVE DOSAGE FORM
1GM/100ML (10MG/ML) OFIRMEV MALLINCKRODT IP N022450 Nov. 2, 2010 RX SOLUTION IV (INFUSION) 9610265 Nov. 13, 2028 MANAGEMENT OF MODERATE TO SEVERE PAIN AS AN ADJUNCT TO OPIOID ANALGESICS
325MG XARTEMIS XR MALLINCKRODT INC N204031 March 11, 2014 DISCN TABLET, EXTENDED RELEASE ORAL 8372432 March 11, 2029 MANAGEMENT OF ACUTE PAIN IN PATIENTS REQUIRING OPIOID ANALGESIA
325MG XARTEMIS XR MALLINCKRODT INC N204031 March 11, 2014 DISCN TABLET, EXTENDED RELEASE ORAL 8668929 March 11, 2029 MANAGEMENT OF ACUTE PAIN IN PATIENTS REQUIRING OPIOID ANALGESIA
325MG XARTEMIS XR MALLINCKRODT INC N204031 March 11, 2014 DISCN TABLET, EXTENDED RELEASE ORAL 8377453 Nov. 19, 2029 MANAGEMENT OF ACUTE PAIN IN PATIENTS REQUIRING OPIOID ANALGESIA
1GM/100ML (10MG/ML) OFIRMEV MALLINCKRODT IP N022450 Nov. 2, 2010 RX SOLUTION IV (INFUSION) 9399012 Sept. 11, 2031 MANAGEMENT OF MILD TO MODERATE PAIN, MANAGEMENT OF MODERATE TO SEVERE PAIN AS AN ADJUNCT TO OPIOID ANALGESICS, REDUCTION IN FEVER THROUGH ANALGESIC AND ANTIPYRETIC ACTIVITY
325MG XARTEMIS XR MALLINCKRODT INC N204031 March 11, 2014 DISCN TABLET, EXTENDED RELEASE ORAL 8741885 May 16, 2032 MANAGEMENT OF ACUTE PAIN IN PATIENTS REQUIRING OPIOID ANALGESIA
325MG XARTEMIS XR MALLINCKRODT INC N204031 March 11, 2014 DISCN TABLET, EXTENDED RELEASE ORAL 9468636 May 16, 2032 MANAGEMENT OF ACUTE PAIN IN PATIENTS REQUIRING OPIOID ANALGESIA

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
1GM/100ML (10MG/ML) OFIRMEV MALLINCKRODT IP N022450 Nov. 2, 2010 RX SOLUTION IV (INFUSION) Jan. 27, 2020 REVISIONS TO THE PACKAGE INSERT BASED ON DATA FROM A RANDOMIZED, PLACEBO CONTROLLED, MULTICENTER STUDY OF INTRAVENOUS ACETAMINOPHEN FOR THE TREATMENT OF ACUTE PAIN IN PEDIATRIC PATIENTS TO FULFILL THE POST-MARKETING REQUIREMENT 1704-1
1GM/100ML (10MG/ML) OFIRMEV MALLINCKRODT IP N022450 Nov. 2, 2010 RX SOLUTION IV (INFUSION) July 27, 2020 PEDIATRIC EXCLUSIVITY

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Transient receptor potential cation channel subfamily V member 1 Ion channel OPENER WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 4.31 WOMBAT-PK CHEMBL
Cannabinoid receptor 1 GPCR AGONIST WOMBAT-PK SCIENTIFIC LITERATURE
Carbonic anhydrase 3 Enzyme Ki 5.15 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 5.21 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 4.97 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 5.04 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 4.15 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 5.39 CHEMBL
Myoglobin Unclassified IC50 5.64 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 4.94 CHEMBL
Nuclear receptor subfamily 1 group I member 3 Nuclear hormone receptor WOMBAT-PK
Carbonic anhydrase 1 Enzyme Ki 5 CHEMBL
Arachidonate 5-lipoxygenase-activating protein Cytosolic other IC50 4.36 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 4.52 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 5.03 CHEMBL
Arachidonate 15-lipoxygenase Enzyme IC50 4.55 DRUG MATRIX

External reference:

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IDSource
CHEBI:46195 CHEBI
DB00316 DRUGBANK_ID
4017513 VUID
N0000145898 NUI
C0000970 UMLSCUI
D00217 KEGG_DRUG
CHEMBL112 ChEMBL_ID
362O9ITL9D UNII
626 INN_ID
5005 MMSL
161 RXNORM
387517004 SNOMEDCT_US
90332006 SNOMEDCT_US
4119 MMSL
d00049 MMSL
4992 MMSL
4017513 VANDF
52845 MMSL
N0000145898 NDFRT
N0000007359 NDFRT
001605 NDDF
D000082 MESH_DESCRIPTOR_UI
1983 PUBCHEM_CID
TYL PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Norco HUMAN PRESCRIPTION DRUG LABEL 2 0023-6002 TABLET 325 mg ORAL ANDA 14 sections
Norco HUMAN PRESCRIPTION DRUG LABEL 2 0023-6021 TABLET 325 mg ORAL ANDA 14 sections
Norco HUMAN PRESCRIPTION DRUG LABEL 2 0023-6022 TABLET 325 mg ORAL ANDA 14 sections
Childrens Dimetapp Multi-Symptom Cold and Flu HUMAN OTC DRUG LABEL 3 0031-2249 LIQUID 320 mg ORAL OTC MONOGRAPH FINAL 9 sections
ROBITUSSIN PEAK COLD DAYTIME COLD PLUS FLU HUMAN OTC DRUG LABEL 3 0031-8721 CAPSULE, LIQUID FILLED 325 mg ORAL OTC MONOGRAPH FINAL 9 sections
ROBITUSSIN PEAK COLD NIGHTTIME COLD PLUS FLU HUMAN OTC DRUG LABEL 3 0031-8722 CAPSULE, LIQUID FILLED 325 mg ORAL OTC MONOGRAPH FINAL 9 sections
ROBITUSSIN PEAK COLD NASAL RELIEF HUMAN OTC DRUG LABEL 2 0031-8731 TABLET 325 mg ORAL OTC monograph final 9 sections
ROBITUSSIN PEAK COLD NIGHTTIME NASAL RELIEF HUMAN OTC DRUG LABEL 3 0031-8732 TABLET 325 mg ORAL OTC monograph final 9 sections
ROBITUSSIN PEAK COLD NIGHTTIME MULTI-SYMPTOM COLD HUMAN OTC DRUG LABEL 3 0031-8735 LIQUID 160 mg ORAL OTC monograph final 9 sections
Robitussin Maximum Strength Severe Cough Plus Sore Throat HUMAN OTC DRUG LABEL 2 0031-8750 LIQUID 650 mg ORAL OTC Monograph Final 9 sections
Robitussin Severe Multi-Symptom Cough Cold Flu HUMAN OTC DRUG LABEL 4 0031-8751 LIQUID 650 mg ORAL OTC monograph final 9 sections
Robitussin Severe Multi-Symptom Cough Cold Flu Nighttime HUMAN OTC DRUG LABEL 3 0031-8752 SOLUTION 650 mg ORAL OTC MONOGRAPH FINAL 9 sections
Oxycodone and Acetaminophen HUMAN PRESCRIPTION DRUG LABEL 2 0054-0551 TABLET 325 mg ORAL ANDA 14 sections
Roxicet HUMAN PRESCRIPTION DRUG LABEL 2 0054-3686 SOLUTION 325 mg ORAL ANDA 13 sections
Roxicet HUMAN PRESCRIPTION DRUG LABEL 2 0054-4650 TABLET 325 mg ORAL ANDA 13 sections
Roxicet HUMAN PRESCRIPTION DRUG LABEL 2 0054-8648 SOLUTION 325 mg ORAL ANDA 13 sections
Roxicet HUMAN PRESCRIPTION DRUG LABEL 2 0054-8650 TABLET 325 mg ORAL ANDA 13 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2000 TABLET, FILM COATED 250 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2021 TABLET, COATED 250 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2035 TABLET, COATED 250 mg ORAL NDA 10 sections
EXCEDRIN HUMAN OTC DRUG LABEL 3 0067-2039 TABLET, FILM COATED 250 mg ORAL NDA 9 sections
Excedrin PM Triple Action Caplets HUMAN OTC DRUG LABEL 3 0067-2056 TABLET, COATED 250 mg ORAL OTC monograph not final 9 sections
COMTREX HUMAN OTC DRUG LABEL 3 0067-2077 TABLET, COATED 325 mg ORAL OTC monograph final 16 sections
COMTREX HUMAN OTC DRUG LABEL 5 0067-2083 KIT 325 mg None OTC monograph final 15 sections
COMTREX HUMAN OTC DRUG LABEL 5 0067-2083 KIT 325 mg None OTC monograph final 15 sections
THERAFLU HUMAN OTC DRUG LABEL 3 0067-6426 POWDER, FOR SOLUTION 500 mg ORAL OTC monograph final 9 sections
Theraflu HUMAN OTC DRUG LABEL 3 0067-7916 POWDER, FOR SOLUTION 650 mg ORAL OTC monograph final 16 sections
Theraflu HUMAN OTC DRUG LABEL 3 0067-7917 POWDER, FOR SOLUTION 650 mg ORAL OTC monograph final 9 sections
THERAFLU HUMAN OTC DRUG LABEL 3 0067-7918 POWDER, FOR SOLUTION 650 mg ORAL OTC monograph final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-8103 TABLET, FILM COATED 250 mg ORAL ANDA 9 sections