acetaminophen cysteine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

acetaminophen cysteine: an acetaminophen metabolite [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	83997
CHEBI ID	177963
MeSH ID	M0190242

Synonyms (14)

Synonym
CHEBI:177963
64014-06-8
(2r)-3-(4-acetamidophenyl)sulanyl-2-aminopropanoic acid
acetaminophen cystein
aa-cysteine
acetaminophen cysteine
l-cysteine, s-(4-(acetylamino)phenyl)-
s-(4-(acetylamino)phenyl)-l-cysteine
(2r)-3-(4-acetamidophenyl)sulfanyl-2-aminopropanoic acid
acetaminophen-cysteine
DTXSID60214000
AKOS028112517
l-cysteine, s-[4-(acetylamino)phenyl]-
PS-12008

Research Excerpts

Toxicity

Excerpt	Reference	Relevance
" Indeed, pretreatment of male CD-1 mice with APAP-CYS before challenge with a threshold toxic dose of APAP resulted in significant enhancement of APAP-induced nephrotoxicity."	( Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity in CD-1 mice: I. Enhancement of acetaminophen nephrotoxicity by acetaminophen-cysteine. Bruno, MK; Cohen, SD; Hennig, GE; Horton, RA; Roberts, JC; Stern, ST, 2005)	0.33
" This APAP-CYS-induced renal GSH depletion could interfere with intrarenal detoxification of APAP or its toxic metabolite N-acetyl-p-benzoquinoneimine (NAPQI) and may be the mechanism responsible for the potentiation of APAP nephrotoxicity."	( Contribution of acetaminophen-cysteine to acetaminophen nephrotoxicity II. Possible involvement of the gamma-glutamyl cycle. Bruno, MK; Cohen, SD; Hill, DW; Horton, RA; Roberts, JC; Stern, ST, 2005)	0.33

Pharmacokinetics

Excerpt	Reference	Relevance
" However, a significantly shorter elimination half-life of PCM was observed in the thalassemic subjects (p<0."	( A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. Chantharaksri, U; Fucharoen, P; Fucharoen, S; Howard, TA; Morales, NP; Sanvarinda, Y; Sirankapracha, P; Tankanitlert, J; Temsakulphong, A; Ware, RE, 2006)	0.33
" Our pharmacokinetic data provide additional evidence that plasma PCM-G is higher in thalassemic patients with hyperbilirubinemia, which could be a casual relationship in regulating the UDP-glucuronosyltransferase expression."	( A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. Chantharaksri, U; Fucharoen, P; Fucharoen, S; Howard, TA; Morales, NP; Sanvarinda, Y; Sirankapracha, P; Tankanitlert, J; Temsakulphong, A; Ware, RE, 2006)	0.33
"The pharmacokinetic (PK) profile of a drug is influenced by several factors, which can lead to a suboptimal dosing regimen in specific patient populations."	( Application of a Volumetric Absorptive Microsampling (VAMS)-Based Method for the Determination of Paracetamol and Four of its Metabolites as a Tool for Pharmacokinetic Studies in Obese and Non-Obese Patients. Boffel, L; De Baerdemaeker, L; Delahaye, L; Stove, CP, 2022)	0.72

Dosage Studied

Excerpt	Relevance	Reference
" It is not clear why regular dosing with paracetamol in haemodialysis patients did not cause the accumulation of paracetamol glucuronide or sulphate as predicted."	( The disposition of paracetamol and its conjugates during multiple dosing in patients with end-stage renal failure maintained on haemodialysis. Martin, U; Prescott, LF; Temple, RM; Winney, RJ, 1993)	0.29
"5, 2, 3, 4, 5, 7, and 9 h after dosing for determination of the plasma levels of PCM and its metabolites by high-performance liquid chromatography."	( A pharmacokinetic study of paracetamol in Thai beta-thalassemia/HbE patients. Chantharaksri, U; Fucharoen, P; Fucharoen, S; Howard, TA; Morales, NP; Sanvarinda, Y; Sirankapracha, P; Tankanitlert, J; Temsakulphong, A; Ware, RE, 2006)	0.33
" However, the concentrations of APAP-CYS during therapeutic dosing, in cases of acetaminophen toxicity from repeated dosing and in cases of hepatic injury from non-acetaminophen hepatotoxins have not been well characterized."	( Acetaminophen-cysteine adducts during therapeutic dosing and following overdose. Dart, RC; Green, JL; Heard, KJ; James, LP; Judge, BS; Rhyee, S; Zolot, L, 2011)	0.37
" Trial 1 consisted of non-drinkers who received APAP for 10 days, Trial 2 consisted of moderate drinkers dosed for 10 days and Trial 3 included subjects who chronically abuse alcohol dosed for 5 days."	( Acetaminophen-cysteine adducts during therapeutic dosing and following overdose. Dart, RC; Green, JL; Heard, KJ; James, LP; Judge, BS; Rhyee, S; Zolot, L, 2011)	0.37
" Adducts are detectable after a few doses and can persist for over a week after dosing is stopped."	( Paracetamol (acetaminophen) protein adduct concentrations during therapeutic dosing. Anderson, V; Bucher-Bartelson, B; Dart, RC; Green, JL; Heard, K, 2016)	0.43
"The pharmacokinetic (PK) profile of a drug is influenced by several factors, which can lead to a suboptimal dosing regimen in specific patient populations."	( Application of a Volumetric Absorptive Microsampling (VAMS)-Based Method for the Determination of Paracetamol and Four of its Metabolites as a Tool for Pharmacokinetic Studies in Obese and Non-Obese Patients. Boffel, L; De Baerdemaeker, L; Delahaye, L; Stove, CP, 2022)	0.72

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
S-conjugate	A bioconjugate containing molecules covalently bonded by a sulphur linkage
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

Pathway	Proteins	Compounds
Acetaminophen Metabolism Pathway	30	16

Research

Studies (23)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	3 (13.04)	18.2507
2000's	8 (34.78)	29.6817
2010's	10 (43.48)	24.3611
2020's	2 (8.70)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.38

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	33.38 (24.57)
Research Supply Index	3.30 (2.92)
Research Growth Index	4.85 (4.65)
Search Engine Demand Index	40.31 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (33.38)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	3 (13.04%)	5.53%
Reviews	1 (4.35%)	6.00%
Case Studies	1 (4.35%)	4.05%
Observational	1 (4.35%)	0.25%
Other	17 (73.91%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
4-nitrophenol 4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.	2.05	1	0	4-nitrophenols	human xenobiotic metabolite; mouse metabolite
acetaminophen Acetaminophen: 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.. paracetamol : A member of the class of phenols that is 4-aminophenol in which one of the hydrogens attached to the amino group has been replaced by an acetyl group.	9.92	24	3	acetamides; phenols	antipyretic; cyclooxygenase 1 inhibitor; cyclooxygenase 2 inhibitor; cyclooxygenase 3 inhibitor; environmental contaminant; ferroptosis inducer; geroprotector; hepatotoxic agent; human blood serum metabolite; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
aminopyrine Aminopyrine: A pyrazolone with analgesic, anti-inflammatory, and antipyretic properties but has risk of AGRANULOCYTOSIS. A breath test with 13C-labeled aminopyrine has been used as a non-invasive measure of CYTOCHROME P-450 metabolic activity in LIVER FUNCTION TESTS.. aminophenazone : A pyrazolone that is 1,2-dihydro-3H-pyrazol-3-one substituted by a dimethylamino group at position 4, methyl groups at positions 1 and 5 and a phenyl group at position 2. It exhibits analgesic, anti-inflammatory, and antipyretic properties.	2.05	1	0	pyrazolone; tertiary amino compound	antipyretic; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
4-nitroanisole 4-nitroanisole: dye intermediate; organic synthesis; structure. 4-nitroanisole : A member of the class of 4-nitroanisoles that is anisole in which one the hydrogen meta to the methoxy group is replaced by a nitro group.	2.05	1	0	4-nitroanisoles
isoxazoles Isoxazoles: Azoles with an OXYGEN and a NITROGEN next to each other at the 1,2 positions, in contrast to OXAZOLES that have nitrogens at the 1,3 positions.. isoxazole : A monocyclic heteroarene with a structure consisting of a 5-membered ring containing three carbon atoms and an oxygen and nitrogen atom adjacent to each other. It is the parent of the class of isoxazoles.. isoxazoles : Oxazoles in which the N and O atoms are adjacent.	2.02	1	0	isoxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.21	1	0	dialdehyde	biomarker
pregnenolone carbonitrile Pregnenolone Carbonitrile: A catatoxic steroid and microsomal enzyme inducer having significant effects on the induction of cytochrome P450. It has also demonstrated the potential for protective capability against acetaminophen-induced liver damage.	1.97	1	0	aliphatic nitrile
n-acetyl-4-benzoquinoneimine N-acetyl-4-benzoquinoneimine: reactive arylating intermediate from acetaminophen & N-hydroxyacetaminophen; structure given in first source	3.42	1	1	ketoimine; quinone imine
acetaminophen sulfate ester acetaminophen sulfate ester: RN given refers to parent cpd; structure given in first source. paracetamol sulfate : An aryl sulfate that is paracetamol in which the hydroxy group has been replaced by a sulfooxy group.	4.91	8	1	acetamides; aryl sulfate	drug metabolite
acetaminophen glucuronide acetaminophen glucuronide: acetaminophen metabolite in rats. acetaminophen O-beta-D-glucosiduronic acid : A beta-D-glucosiduronic acid that is the O-glucuronide of paracetamol (acetaminophen).	4.79	7	1	beta-D-glucosiduronic acid	drug metabolite
acetaminophen mercapturate S-(5-acetamido-2-hydroxyphenyl)-N-acetyl-L-cysteine : An S-substituted N-acetyl-L-cysteine in which the S-substitutuent is specified as 5-acetamido-2-hydroxyphenyl.	4.34	4	1	acetamides; organic sulfide; phenols; S-substituted N-acetyl-L-cysteine	drug metabolite; human urinary metabolite; rat metabolite
acivicin [no description available]	2.02	1	0	isoxazoles; non-proteinogenic L-alpha-amino acid; organochlorine compound	antileishmanial agent; antimetabolite; antimicrobial agent; antineoplastic agent; EC 2.3.2.2 (gamma-glutamyltransferase) inhibitor; glutamine antagonist; metabolite
bilirubin [no description available]	2.03	1	0	biladienes; dicarboxylic acid	antioxidant; human metabolite; mouse metabolite
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.21	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
cysteine Cysteine: A thiol-containing non-essential amino acid that is oxidized to form CYSTINE.. L-cysteinium : The L-enantiomer of cysteinium.. cysteine : A sulfur-containing amino acid that is propanoic acid with an amino group at position 2 and a sulfanyl group at position 3.	9.96	25	3	cysteinium	fundamental metabolite
nitrophenols Nitrophenols: PHENOLS carrying nitro group substituents.	2.05	1	0
oxypurinol Oxypurinol: A xanthine oxidase inhibitor.. alloxanthine : A pyrazolopyrimidine that is 4,5,6,7-tetrahydro-H-pyrazolo[3,4-d]pyrimidine substituted by oxo groups at positions 4 and 6.	2.1	1	0	pyrazolopyrimidine	drug metabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.1	1	0	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger
metallothionein Metallothionein: A low-molecular-weight (approx. 10 kD) protein occurring in the cytoplasm of kidney cortex and liver. It is rich in cysteinyl residues and contains no aromatic amino acids. Metallothionein shows high affinity for bivalent heavy metals.	2.1	1	0

Condition	Relationship Strength	Studies	Trials
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	3.33	4	0
Acute Liver Injury, Drug-Induced [description not available]	4.88	7	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	4.88	7	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.21	1	0
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	4.57	5	1
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.11	1	0
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.11	1	0
Acute Hepatic Failure [description not available]	6.5	11	0
Liver Failure, Acute A form of rapid-onset LIVER FAILURE, also known as fulminant hepatic failure, caused by severe liver injury or massive loss of HEPATOCYTES. It is characterized by sudden development of liver dysfunction and JAUNDICE. Acute liver failure may progress to exhibit cerebral dysfunction even HEPATIC COMA depending on the etiology that includes hepatic ISCHEMIA, drug toxicity, malignant infiltration, and viral hepatitis such as post-transfusion HEPATITIS B and HEPATITIS C.	6.5	11	0
Ache [description not available]	2.48	2	0
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	2.48	2	0
Morbid Obesity [description not available]	3.04	1	0
Obesity, Morbid The condition of weighing two, three, or more times the ideal weight, so called because it is associated with many serious and life-threatening disorders. In the BODY MASS INDEX, morbid obesity is defined as having a BMI greater than 40.0 kg/m2.	3.04	1	0
Alcohol Abuse [description not available]	3.45	1	1
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking.	3.45	1	1
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4)	3.45	1	1
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.43	2	0
Anemia, Cooley's [description not available]	2.03	1	0
beta-Thalassemia A disorder characterized by reduced synthesis of the beta chains of hemoglobin. There is retardation of hemoglobin A synthesis in the heterozygous form (thalassemia minor), which is asymptomatic, while in the homozygous form (thalassemia major, Cooley's anemia, Mediterranean anemia, erythroblastic anemia), which can result in severe complications and even death, hemoglobin A synthesis is absent.	2.03	1	0
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	6.31	9	0
Benign Neoplasms [description not available]	3.42	1	1
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	3.42	1	1
Chronic Kidney Failure [description not available]	1.98	1	0
Kidney Failure, Chronic The end-stage of CHRONIC RENAL INSUFFICIENCY. It is characterized by the severe irreversible kidney damage (as measured by the level of PROTEINURIA) and the reduction in GLOMERULAR FILTRATION RATE to less than 15 ml per min (Kidney Foundation: Kidney Disease Outcome Quality Initiative, 2002). These patients generally require HEMODIALYSIS or KIDNEY TRANSPLANTATION.	1.98	1	0

chemdatabank.com