3-hydroxymethylantipyrine profile

3-hydroxymethylantipyrine : A pyrazolone that is antipyrine in which one of the hydrogens of the 5-methyl group is substituted by a hydroxymethyl group. It is a metabolite of the analgesic drug, antipyrene. [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]

ID Source	ID
PubMed CID	123963
CHEBI ID	145210
MeSH ID	M0099725

Synonym
3-hydroxymethylantipyrine
5-(hydroxymethyl)-1-methyl-2-phenylpyrazol-3-one
5-(hydroxymethyl)-1-methyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one
CHEBI:145210
1,2-dihydro-5-(hydroxymethyl)-1-methyl-2-phenyl-3h-pyrazol-3-one
2-methyl-3-(hydroxymethyl)-1-phenyl-3-pyrazolin-5-one
18125-49-0
5-(hydroxymethyl)-1-methyl-2-phenyl-1h-pyrazol-3(2h)-one
3-hmap
3h-pyrazol-3-one, 1,2-dihydro-5-(hydroxymethyl)-1-methyl-2-phenyl-
3f5ys569eb ,
unii-3f5ys569eb
DTXSID00171087
1-phenyl-3-hydroxymethyl-2-methyl-3-pyrazolin-5-one
3-(hydroxymethyl)-2-methyl-1-phenyl-3-pyrazolin-5-one
hydroxymethylantipyrine
CS-0246829
5-(hydroxymethyl)-1-methyl-2-phenyl-2,3-dihydro-1h-pyrazol-3-one
EN300-344575

Excerpt	Reference	Relevance
"01) by verapamil (80 mg three times daily for 2 days prior to antipyrine administration and 2 days following) while half-life was increased from 13."	( The effect of verapamil on antipyrine pharmacokinetics and metabolism in man. Bach, D; Blevins, R; Edwards, DJ; Kerner, N; Rubenfire, M, 1986)	0.27
" The first three months of life were characterised by a steady decrease in the apparent volume of distribution (aVd) and half-life (t0."	( Effect of age on the pharmacokinetics of antipyrine in calves. Janus, K; Suszycka, J, 1996)	0.29
" The plasma elimination half-life of antipyrine was significantly elevated by 23% at 11 weeks postinfection (p."	( Effect of experimental fasciolosis on antipyrine metabolism and clearance in water buffaloes. Bayón, JE; Ferre, I; González-Gallego, J; Jiang, SX; Mao, XZ, 2000)	0.31

Excerpt	Relevance	Reference
" Unknown additional peaks were detected in urine after NORA dosing but not after HMA or OHA administration."	( The pharmacokinetics of antipyrine and three of its metabolites in the rabbit: intravenous administration of pure metabolites. Abul-Hajj, Y; Awni, WM; St Peter, JV, 1991)	0.28
" Mefloquine (750 mg) had no significant effect on salivary kinetics of antipyrine or on the metabolic clearance of antipyrine to its three main metabolites, 3-hydroxymethylantipyrine, 4-hydroxyantipyrine and norantipyrine, when antipyrine was administered either 2 h or 2 weeks after dosing with mefloquine."	( The pharmacokinetics of mefloquine in man: lack of effect of mefloquine on antipyrine metabolism. Back, DJ; Breckenridge, AM; Howells, RE; Rivière, JH, 1985)	0.47

Role	Description
drug metabolite	null
human urinary metabolite	Any metabolite (endogenous or exogenous) found in human urine samples.
[role 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]

Class	Description
pyrazolone	A member of the class of pyrazoles in which one of the carbons of the pyrazole ring is substituted by an oxo group.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	28 (56.00)	18.7374
1990's	17 (34.00)	18.2507
2000's	3 (6.00)	29.6817
2010's	1 (2.00)	24.3611
2020's	1 (2.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (3.77%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	51 (96.23%)	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
3-methylcholanthrene Methylcholanthrene: A carcinogen that is often used in experimental cancer studies.. 3-methylcholanthrene : A pentacyclic ortho- and peri-fused polycyclic arene consisting of a dihydrocyclopenta[ij]tetraphene ring system with a methyl substituent at the 3-position.	1.96	1	0	ortho- and peri-fused polycyclic arene	aryl hydrocarbon receptor agonist; carcinogenic agent
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.	1.96	1	0	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
alaproclate alaproclate: specific 5-hydroxytryptamine uptake inhibitors; RN given refers to (DL)-isomer	1.96	1	0	alpha-amino acid ester
theophylline [no description available]	1.96	1	0	dimethylxanthine	adenosine receptor antagonist; anti-asthmatic drug; anti-inflammatory agent; bronchodilator agent; drug metabolite; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; fungal metabolite; human blood serum metabolite; immunomodulator; muscle relaxant; vasodilator agent
antipyrine Antipyrine: An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29). antipyrine : A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2.	7.16	50	2	pyrazolone	antipyretic; cyclooxygenase 3 inhibitor; environmental contaminant; non-narcotic analgesic; non-steroidal anti-inflammatory drug; xenobiotic
verapamil Verapamil: A calcium channel blocker that is a class IV anti-arrhythmia agent.. verapamil : A racemate comprising equimolar amounts of dexverapamil and (S)-verapamil. An L-type calcium channel blocker of the phenylalkylamine class, it is used (particularly as the hydrochloride salt) in the treatment of hypertension, angina pectoris and cardiac arrhythmia, and as a preventive medication for migraine.. 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile : A tertiary amino compound that is 3,4-dimethoxyphenylethylamine in which the hydrogens attached to the nitrogen are replaced by a methyl group and a 4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl group.	1.96	1	0	aromatic ether; nitrile; polyether; tertiary amino compound
cimetidine Cimetidine: A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.. cimetidine : A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H2-receptor antagonist that inhibits the production of acid in stomach.	2.38	2	0	aliphatic sulfide; guanidines; imidazoles; nitrile	adjuvant; analgesic; anti-ulcer drug; H2-receptor antagonist; P450 inhibitor
ciprofloxacin Ciprofloxacin: A broad-spectrum antimicrobial carboxyfluoroquinoline.. ciprofloxacin : A quinolone that is quinolin-4(1H)-one bearing cyclopropyl, carboxylic acid, fluoro and piperazin-1-yl substituents at positions 1, 3, 6 and 7, respectively.	3.36	1	1	aminoquinoline; cyclopropanes; fluoroquinolone antibiotic; N-arylpiperazine; quinolinemonocarboxylic acid; quinolone antibiotic; quinolone; zwitterion	antibacterial drug; antiinfective agent; antimicrobial agent; DNA synthesis inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; environmental contaminant; topoisomerase IV inhibitor; xenobiotic
edaravone [no description available]	6.72	32	2	pyrazolone	antioxidant; radical scavenger
phenobarbital Phenobarbital: A barbituric acid derivative that acts as a nonselective central nervous system depressant. It potentiates GAMMA-AMINOBUTYRIC ACID action on GABA-A RECEPTORS, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations.. phenobarbital : A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by ethyl and phenyl groups.	1.98	1	0	barbiturates	anticonvulsant; drug allergen; excitatory amino acid antagonist; sedative
proadifen Proadifen: An inhibitor of drug metabolism and CYTOCHROME P-450 ENZYME SYSTEM activity.	1.98	1	0	diarylmethane
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	1.96	1	0	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
chloramphenicol Amphenicol: Chloramphenicol and its derivatives.	1.97	1	0	C-nitro compound; carboxamide; diol; organochlorine compound	antibacterial drug; antimicrobial agent; Escherichia coli metabolite; geroprotector; Mycoplasma genitalium metabolite; protein synthesis inhibitor
chlorodiphenyl (54% chlorine) Chlorodiphenyl (54% Chlorine): A mixture of polychlorinated biphenyls that induces hepatic microsomal UDP-glucuronyl transferase activity towards thyroxine.. Aroclor 1254 : A mixture of polychlorobiphenyls of unspecified composition, containing 54% chlorine (X = Cl or H).	1.96	1	0
n-demethylantipyrine [no description available]	2.65	3	0	pyrazoles; ring assembly
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).	1.96	1	0	beta-D-glucosiduronic acid	drug metabolite
9-hydroxyellipticine 9-hydroxyellipticine: RN given refers to parent cpd. 9-hydroxyellipticine : A organic heterotetracyclic compound that is ellipticine in which the hydrogen at position 9 has been replaced by a hydroxy group.	1.96	1	0	organic heterotetracyclic compound; organonitrogen heterocyclic compound	antineoplastic agent
4-hydroxyantipyrine 4-hydroxyantipyrine: metabolite of antipyrine; structure in third source	6.98	42	2	pyrazoles; ring assembly
mefloquine Mefloquine: A phospholipid-interacting antimalarial drug (ANTIMALARIALS). It is very effective against PLASMODIUM FALCIPARUM with very few side effects.. mefloquine : A racemate composed of (+)-(11R,2'S)- and (-)-(11S,2'R)-enantiomers of mefloquine. An antimalarial agent which acts as a blood schizonticide; its mechanism of action is unknown.	1.96	1	0

Condition	Relationship Strength	Studies	Trials
Diseases, Occupational [description not available]	2.02	1	0
Alcoholic Cirrhosis [description not available]	1.96	1	0
Liver Cirrhosis, Alcoholic FIBROSIS of the hepatic parenchyma due to chronic excess ALCOHOL DRINKING.	1.96	1	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	1.96	1	0
Chronic Illness [description not available]	1.98	1	0
Hepatitis, Viral, Non-A, Non-B, Parenterally-Transmitted [description not available]	1.98	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	1.98	1	0
Hepatitis C INFLAMMATION of the LIVER in humans caused by HEPATITIS C VIRUS, a single-stranded RNA virus. Its incubation period is 30-90 days. Hepatitis C is transmitted primarily by contaminated blood parenterally and is often associated with transfusion and intravenous drug abuse. However, in a significant number of cases, the source of hepatitis C infection is unknown.	1.98	1	0
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time.	4.47	5	1
Blood Pressure, High [description not available]	1.99	1	0
Chronic Kidney Failure [description not available]	2.38	2	0
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	1.99	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.	2.38	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	1.99	1	0
Fasciola Infection [description not available]	2	1	0
Fascioliasis Liver disease caused by infections with parasitic flukes of the genus FASCIOLA, such as FASCIOLA HEPATICA.	2	1	0
Adenocarcinoma, Basal Cell [description not available]	1.98	1	0
Cancer of Liver [description not available]	2.38	2	0
Colorectal Cancer [description not available]	1.98	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	1.98	1	0
Liver Neoplasms Tumors or cancer of the LIVER.	2.38	2	0
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	1.98	1	0
Hepatocellular Carcinoma [description not available]	1.97	1	0
Cirrhosis, Liver [description not available]	1.97	1	0
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	1.97	1	0
Liver Cirrhosis Liver disease in which the normal microcirculation, the gross vascular anatomy, and the hepatic architecture have been variably destroyed and altered with fibrous septa surrounding regenerated or regenerating parenchymal nodules.	1.97	1	0
Palmoplantaris Pustulosis [description not available]	1.96	1	0
Psoriasis A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.	1.96	1	0
Liver Dysfunction [description not available]	1.96	1	0
Liver Diseases Pathological processes of the LIVER.	1.96	1	0

3-hydroxymethylantipyrine

Description

Cross-References

Synonyms (19)

Research Excerpts

Pharmacokinetics

Dosage Studied

Roles (2)

Drug Classes (1)

Research

Studies (50)

Market Indicators

Research Demand Index: 10.52

Study Types