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paracetamol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
	52	103-90-2

Description:

Molecule	Description
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 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

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

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
3	g	O
3	g	P
3	g	R

ADMET properties:

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Property	Value	Reference
BA (Bioavailability)	88 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance)	5 mL/min/kg	Lombardo F, Berellini G, Obach RS
MRTD (Maximum Recommended Therapeutic Daily Dose)	330.76 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	23.70 mg/mL	Benet LZ, Broccatelli F, Oprea TI
t_half (Half-life)	2.50 hours	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	1 L/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.52 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Feb. 24, 2023	PMDA	AYUMI PHARMACEUTICAL CORPORATION
Nov. 7, 1968	FDA	POLYMEDICA

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	2741.57	11.19	9119	955176	238131	62286596
Intentional overdose	1466.76	11.19	3383	960912	70769	62453958
Completed suicide	1320.18	11.19	5033	959262	140640	62384087
Acute hepatic failure	1187.64	11.19	1429	962866	16898	62507829
Overdose	1043.09	11.19	3977	960318	111101	62413626
Analgesic drug level increased	960.81	11.19	541	963754	1831	62522896
Drug ineffective	850.06	11.19	11000	953295	1033765	61490962
Hepatocellular injury	706.07	11.19	1392	962903	25989	62498738
Poisoning deliberate	565.01	11.19	772	963523	10446	62514281
Suicide attempt	563.71	11.19	2120	962175	58798	62465929

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FDA Adverse Event Reporting System (Male)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	1113.55	11.72	5286	441593	195076	34314976
Drug ineffective	717.51	11.72	3208	443671	453543	34056509
Intentional overdose	603.40	11.72	1561	445318	42113	34467939
Overdose	579.30	11.72	2503	444376	88556	34421496
Infusion related reaction	565.62	11.72	1726	445153	51331	34458721
Acute hepatic failure	550.30	11.72	784	446095	13290	34496762
Completed suicide	453.00	11.72	2461	444418	95707	34414345
Hepatocellular injury	395.24	11.72	876	446003	21335	34488717
Analgesic drug level increased	392.11	11.72	200	446679	656	34509396
Exposure to toxic agent	299.57	11.72	298	446581	3377	34506675

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FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Toxicity to various agents	3526.35	11.21	13875	1159126	407665	78163722
Intentional overdose	2042.78	11.21	4693	1168308	101267	78470120
Completed suicide	1900.29	11.21	7902	1165099	237865	78333522
Acute hepatic failure	1654.46	11.21	2127	1170874	27986	78543401
Overdose	1408.19	11.21	5904	1167097	178302	78393085
Analgesic drug level increased	1317.71	11.21	728	1172273	2450	78568937
Hepatocellular injury	1043.12	11.21	2220	1170781	45373	78526014
Drug ineffective	984.01	11.21	10674	1162327	1070239	77501148
Exposure to toxic agent	830.53	11.21	839	1172162	8319	78563068
Poisoning deliberate	713.80	11.21	1114	1171887	17714	78553673

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FDA Adverse Event Reporting System (Pediatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Accidental overdose	30.99	13.82	17	894	90	88791
Analgesic drug level increased	25.23	13.82	7	904	0	88881
Overdose	16.94	13.82	9	902	44	88837
Incorrect dosage administered	15.15	13.82	6	905	12	88869

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Pharmacologic Action:

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Source	Code	Description
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	N02BE01	NERVOUS SYSTEM ANALGESICS OTHER ANALGESICS AND ANTIPYRETICS Anilides
ATC	N02BE51	NERVOUS SYSTEM ANALGESICS OTHER ANALGESICS AND ANTIPYRETICS Anilides
ATC	N02BE71	NERVOUS SYSTEM ANALGESICS OTHER ANALGESICS AND ANTIPYRETICS Anilides
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory agent
CHEBI has role	CHEBI:35493	anti-pyretic
CHEBI has role	CHEBI:35703	Xenobiotic

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
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

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.69	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
1GM/100ML (10MG/ML)	OFIRMEV	MALLINCKRODT HOSP	N022450	Nov. 2, 2010	DISCN	SOLUTION	INTRAVENOUS	10383834	Nov. 13, 2028	MODIFIED DOSING REGIMEN FOR THE MANAGEMENT OF MILD TO MODERATE PAIN
1GM/100ML (10MG/ML)	OFIRMEV	MALLINCKRODT HOSP	N022450	Nov. 2, 2010	DISCN	SOLUTION	INTRAVENOUS	10383834	Nov. 13, 2028	MODIFIED DOSING REGIMEN FOR THE REDUCTION OF FEVER
1GM/100ML (10MG/ML)	OFIRMEV	MALLINCKRODT HOSP	N022450	Nov. 2, 2010	DISCN	SOLUTION	INTRAVENOUS	9610265	Nov. 13, 2028	MODIFIED DOSING REGIMEN FOR THE MANAGEMENT OF MODERATE TO SEVERE PAIN WITH ADJUNCTIVE OPIOID ANALGESICS
1GM/100ML (10MG/ML)	OFIRMEV	MALLINCKRODT HOSP	N022450	Nov. 2, 2010	DISCN	SOLUTION	INTRAVENOUS	9987238	Nov. 13, 2028	MODIFIED DOSING REGIMEN FOR THE MANAGEMENT OF MILD TO MODERATE PAIN OR MANAGEMENT OF MODERATE TO SEVERE PAIN AS AN ADJUNCT TO OPIOID ANALGESICS
1GM/100ML (10MG/ML)	OFIRMEV	MALLINCKRODT HOSP	N022450	Nov. 2, 2010	DISCN	SOLUTION	INTRAVENOUS	9399012	Sept. 11, 2031	MODIFIED DOSING REGIMEN FOR THE MANAGEMENT OF MILD TO MODERATE PAIN OR MANAGEMENT OF MODERATE TO SEVERE PAIN AS AN ADJUNCT TO OPIOID ANALGESICS
1GM/100ML (10MG/ML)	OFIRMEV	MALLINCKRODT HOSP	N022450	Nov. 2, 2010	DISCN	SOLUTION	INTRAVENOUS	9399012	Sept. 11, 2031	MODIFIED DOSING REGIMEN FOR THE REDUCTION OF FEVER
325MG;7.5MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	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
325MG;7.5MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	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;7.5MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	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;7.5MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons	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

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
250MG;125MG	ADVIL DUAL ACTION WITH ACETAMINOPHEN	GLAXOSMITHKLINE	N211733	Feb. 28, 2020	OTC	TABLET	ORAL	Feb. 28, 2023	NEW PRODUCT
325MG;97.5MG	COMBOGESIC	AFT PHARMS LTD	N209471	March 1, 2023	RX	TABLET	ORAL	March 1, 2026	NEW PRODUCT

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Prostaglandin G/H synthase 2	Enzyme	P35354	PGH2_HUMAN	INHIBITOR	IC50	4.31	WOMBAT-PK	CHEMBL
Transient receptor potential cation channel subfamily V member 1	Ion channel	Q8NER1	TRPV1_HUMAN	OPENER			WOMBAT-PK	CHEMBL
Cannabinoid receptor 1	GPCR	P21554	CNR1_HUMAN	AGONIST			WOMBAT-PK	SCIENTIFIC LITERATURE
Carbonic anhydrase 2	Enzyme	P00918	CAH2_HUMAN		Ki	5.21	CHEMBL
Carbonic anhydrase 1	Enzyme	P00915	CAH1_HUMAN		Ki	5	CHEMBL
Carbonic anhydrase 4	Enzyme	P22748	CAH4_HUMAN		Ki	4.94	CHEMBL
Carbonic anhydrase 9	Enzyme	Q16790	CAH9_HUMAN		Ki	4.15	CHEMBL
Carbonic anhydrase 12	Enzyme	O43570	CAH12_HUMAN		Ki	5.39	CHEMBL
Carbonic anhydrase 7	Enzyme	P43166	CAH7_HUMAN		Ki	5.04	CHEMBL
Carbonic anhydrase 3	Enzyme	P07451	CAH3_HUMAN		Ki	5.15	CHEMBL

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External reference:

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ID	Source
NNS	PDB_CHEM_ID
001605	NDDF
161	RXNORM
1983	PUBCHEM_CID
362O9ITL9D	UNII
387517004	SNOMEDCT_US
4017513	VUID
4017513	VANDF
4119	MMSL
4973	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Butalbital, Acetaminophen, Caffeine and Codeine Phosphate	HUMAN PRESCRIPTION DRUG LABEL	4	0054-0650	CAPSULE	300 mg	ORAL	ANDA	33 sections
Butalbital, Acetaminophen, Caffeine and Codeine Phosphate	HUMAN PRESCRIPTION DRUG LABEL	4	0054-0650	CAPSULE	300 mg	ORAL	ANDA	33 sections
Butalbital, Acetaminophen, Caffeine and Codeine Phosphate	HUMAN PRESCRIPTION DRUG LABEL	4	0054-3000	CAPSULE	325 mg	ORAL	ANDA	33 sections
Butalbital, Acetaminophen, Caffeine and Codeine Phosphate	HUMAN PRESCRIPTION DRUG LABEL	4	0054-3000	CAPSULE	325 mg	ORAL	ANDA	33 sections
Childrens Dimetapp Multi-Symptom Cold and Flu	HUMAN OTC DRUG LABEL	3	0031-2249	LIQUID	320 mg	ORAL	Unapproved drug other	17 sections
ExcedrinExtra Strength Geltabs	HUMAN OTC DRUG LABEL	3	0067-2021	TABLET, COATED	250 mg	ORAL	OTC monograph not final	14 sections
ExcedrinExtra Strength Pain Reliever	HUMAN OTC DRUG LABEL	3	0067-2000	TABLET, FILM COATED	250 mg	ORAL	OTC monograph not final	13 sections
ExcedrinExtra Strength Pain Reliever	HUMAN OTC DRUG LABEL	3	0067-2000	TABLET, FILM COATED	250 mg	ORAL	OTC monograph not final	13 sections
ExcedrinExtra Strength Pain Reliever	HUMAN OTC DRUG LABEL	3	0067-2001	TABLET, FILM COATED	250 mg	ORAL	OTC monograph not final	15 sections
ExcedrinExtra Strength Pain Reliever	HUMAN OTC DRUG LABEL	3	0067-2001	TABLET, FILM COATED	250 mg	ORAL	OTC monograph not final	15 sections

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