Page last updated: 2024-09-03

3-hydroxymethylantipyrine and 4-hydroxyantipyrine

3-hydroxymethylantipyrine has been researched along with 4-hydroxyantipyrine in 42 studies

Compound Research Comparison

Studies
(3-hydroxymethylantipyrine)
Trials
(3-hydroxymethylantipyrine)
Recent Studies (post-2010)
(3-hydroxymethylantipyrine)
Studies
(4-hydroxyantipyrine)
Trials
(4-hydroxyantipyrine)
Recent Studies (post-2010) (4-hydroxyantipyrine)
53226623

Research

Studies (42)

TimeframeStudies, this research(%)All Research%
pre-199025 (59.52)18.7374
1990's15 (35.71)18.2507
2000's2 (4.76)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80

Authors

AuthorsStudies
Belwon, S; Dengler, HJ; Edeki, T; Funke, C; Lindecken, KD; Robertz-Vaupel, GM1
Kolker, HJ; Lohuis, JA; Nijmeijer, SM; Noordhoek, J; van Miert, AS; Witkamp, RF1
Abul-Hajj, Y; Awni, WM; St Peter, JV1
Edwards, DJ; Krakovsky, DJ; Rybak, MJ; Steinberg, JD; Waite, NM; Warbasse, LH1
Van Bezooijen, CF; Van Geel, CA1
Shrewsbury, RP; White, LG3
Brendel, E; de Mey, C; Meineke, I1
Awni, WM; St Peter, JV1
Imai, Y; Inada, M; Inui, Y; Ito, N; Kawata, S; Matsuda, Y; Miyoshi, S; Noda, S; Saitoh, R; Tamura, S1
Houston, JB; Shaw, PN1
Breimer, DD; Janssens, AR; Koch, CW; Spoelstra, P; Teunissen, MW; van Duijn, W; Weeda, B1
Bässmann, H; Böttcher, J; Lehmann, WD; Schiebel, HM; Schüppel, R1
Browne, TR; Greenblatt, DJ; LeDuc, BW; Mikati, MA; Pylilo, RJ; Szabo, GK1
Chenery, RJ; Jennings, P; Mason, PA; Norman, SJ; Oldham, HG; Standring, P1
Bach, D; Blevins, R; Edwards, DJ; Kerner, N; Rubenfire, M1
Chiba, K; Ishizaki, T; Kubota, K; Nakagawa, A; Nakamura, K; Takagi, A1
Back, DJ; Breckenridge, AM; Howells, RE; Rivière, JH1
Boeijinga, JK; Breimer, DD; De Leede, LG; Teunissen, MW1
Breimer, DD; Kampf, D; Roots, I; Teunissen, MW; Vermeulen, NP1
Pilsgaard, H; Poulsen, HE1
Bässmann, H; Böttcher, J; Schüppel, R1
Breimer, DD; Teunissen, MW; Vinnars, E; Wahlén, A1
Nash, RM; Passananti, GT; Penno, MB; Stein, L; Vesell, ES1
Breimer, DD; Joeres, RP; Teunissen, MW; Vermeulen, NP1
Slusher, LB; Vesell, ES1
Penno, MB; Vesell, ES1
Chiba, K; Ishizaki, T; Nakagawa, A; Nakamura, K1
Inaba, T; Kalow, W; Tang, BK; Uchino, H1
Blair, IA; Boobis, AR; Brodie, MJ; Davies, DS; Kahn, GC1
Ali, HA; Ali, MA; Døssing, M; el-Yazigi, A; Ernst, P; Khan, B; Raines, DA; Saour, J; Sieck, JO1
Ali, HA; Døssing, M; el-Yazigi, A; Ernst, P; Raines, DA; Saour, J; Sieck, JO1
Cosme, J; Eichelbaum, M; Engel, G; Heidemann, H; Hofmann, U1
Janus, K; Suszycka, J2
Sharer, JE; Wrighton, SA1
Janus, K; Muszczynski, Z; Suszycka, J1
Lanchote, VL; Ping, WC; Santos, SR1
Almar, M; González-Gallego, J; González-Sastre, M; Jorquera, F; Pozuelo, M; Sansegundo, D1
García-López, J; González-Gallego, J; Jorquera, F; Mauriz, JL; Tabernero, B; Villa, JG1
Bayón, JE; Ferre, I; González-Gallego, J; Jiang, SX; Mao, XZ1

Trials

2 trial(s) available for 3-hydroxymethylantipyrine and 4-hydroxyantipyrine

ArticleYear
Influence of subject age on the inhibition of oxidative metabolism by ciprofloxacin.
    Antimicrobial agents and chemotherapy, 1991, Volume: 35, Issue:1

    Topics: Adult; Aged; Aged, 80 and over; Aging; Antipyrine; Ciprofloxacin; Edaravone; Female; Humans; Male; Oxidation-Reduction; Prospective Studies

1991
Elimination studies of antipyrine and its metabolites in healthy Saudi Arabians.
    Human & experimental toxicology, 1994, Volume: 13, Issue:10

    Topics: Administration, Oral; Adolescent; Adult; Antipyrine; Asian People; Black People; Chromatography, High Pressure Liquid; Edaravone; Female; Humans; Male; Metabolic Clearance Rate; Saudi Arabia; White People

1994

Other Studies

40 other study(ies) available for 3-hydroxymethylantipyrine and 4-hydroxyantipyrine

ArticleYear
Disposition of antipyrine in patients with extensive metastatic liver disease.
    European journal of clinical pharmacology, 1992, Volume: 42, Issue:5

    Topics: Adenocarcinoma; Aged; Antipyrine; Colorectal Neoplasms; Edaravone; Female; Humans; Liver Neoplasms; Male; Middle Aged

1992
Species- and sex-related differences in the plasma clearance and metabolite formation of antipyrine. A comparative study in four animal species: cattle, goat, rat and rabbit.
    Xenobiotica; the fate of foreign compounds in biological systems, 1991, Volume: 21, Issue:11

    Topics: Animals; Antipyrine; Cattle; Female; Goats; Half-Life; Male; Rabbits; Rats; Rats, Inbred Strains; Sex Characteristics; Species Specificity

1991
The pharmacokinetics of antipyrine and three of its metabolites in the rabbit: intravenous administration of pure metabolites.
    Pharmaceutical research, 1991, Volume: 8, Issue:12

    Topics: Animals; Antipyrine; Chromatography, High Pressure Liquid; Edaravone; Injections, Intravenous; Male; Mass Spectrometry; Rabbits

1991
The effect of age on the oxidative metabolism of antipyrine by uninduced microsomal fractions of rat liver.
    Mechanisms of ageing and development, 1990, Apr-09, Volume: 53, Issue:2

    Topics: Aging; Animals; Antipyrine; Cytochrome P-450 Enzyme System; Edaravone; In Vitro Techniques; Isoenzymes; Kinetics; Male; Microsomes, Liver; Oxidation-Reduction; Rats; Rats, Inbred BN

1990
Evaluation of cytochrome P-450 mediated metabolism of antipyrine in the rat at different extents of fluosol-DA hemodilution.
    Research communications in chemical pathology and pharmacology, 1990, Volume: 67, Issue:3

    Topics: Animals; Antipyrine; Blood Substitutes; Cytochrome P-450 Enzyme System; Drug Combinations; Fluorocarbons; Hemodilution; Hydroxyethyl Starch Derivatives; Metabolic Clearance Rate; Rats

1990
Assay of antipyrine and its main metabolites 3-hydroxymethylantipyrine, norantipyrine and 4-hydroxyantipyrine in urine.
    Journal of pharmaceutical and biomedical analysis, 1989, Volume: 7, Issue:12

    Topics: Antipyrine; Chromatography, High Pressure Liquid; Edaravone; Glucuronidase; Humans; Hydrogen-Ion Concentration; Indicators and Reagents; Spectrophotometry, Ultraviolet

1989
Modified high-performance liquid chromatographic assay for antipyrine and its three major metabolites in urine.
    Journal of chromatography, 1989, Sep-29, Volume: 494

    Topics: Antipyrine; Chromatography, High Pressure Liquid; Edaravone; Humans

1989
The effect of moderate fluosol-DA hemodilution on gender specific metabolism of antipyrine.
    Research communications in chemical pathology and pharmacology, 1989, Volume: 64, Issue:3

    Topics: Animals; Antipyrine; Drug Combinations; Female; Fluorocarbons; Half-Life; Hemodilution; Hydroxyethyl Starch Derivatives; Injections, Intravenous; Male; Rats; Rats, Inbred Strains; Sex Factors

1989
[Alterations of urinary excretion of antipyrine metabolites in patients with cirrhosis of the liver].
    Nihon Shokakibyo Gakkai zasshi = The Japanese journal of gastro-enterology, 1987, Volume: 84, Issue:11

    Topics: Antipyrine; Carcinoma, Hepatocellular; Edaravone; Female; Humans; Liver Cirrhosis; Liver Neoplasms; Male; Middle Aged

1987
Temporal effects on antipyrine metabolite kinetics in Aroclor 1254-treated rats.
    Toxicology and applied pharmacology, 1986, Jun-30, Volume: 84, Issue:2

    Topics: Animals; Antipyrine; Aroclors; Breath Tests; Carbon Dioxide; Carbon Radioisotopes; Chlorodiphenyl (54% Chlorine); Chromatography, High Pressure Liquid; Cytochrome P-450 Enzyme System; Edaravone; Enzyme Induction; Half-Life; Injections, Intraperitoneal; Kinetics; Liver; Male; Rats; Rats, Inbred Strains

1986
Antipyrine clearance and metabolite formation: the influence of liver volume and smoking.
    European journal of clinical investigation, 1986, Volume: 16, Issue:4

    Topics: Adult; Antipyrine; Cytochrome P-450 Enzyme System; Edaravone; Female; Humans; Kinetics; Liver; Male; Middle Aged; Organ Size; Smoking

1986
Investigations on antipyrine metabolism V. Differentiation of two isomeric hydroxyantipyrine glucuronides by field desorption and fast atom bombardment mass spectrometry.
    Biomedical mass spectrometry, 1985, Volume: 12, Issue:5

    Topics: Antipyrine; Chemical Phenomena; Chemistry, Physical; Glucuronates; Humans; Isomerism; Male; Mass Spectrometry

1985
Some insights into the variations in antipyrine pharmacokinetics in the rat.
    Research communications in chemical pathology and pharmacology, 1988, Volume: 62, Issue:1

    Topics: Animals; Antipyrine; Injections, Intravenous; Kinetics; Rats; Rats, Inbred Strains

1988
Improved high-performance liquid chromatographic assay of antipyrine, hydroxymethylantipyrine, 4-hydroxyantipyrine and norantipyrine in urine.
    Journal of chromatography, 1988, Dec-09, Volume: 433

    Topics: Antipyrine; Chromatography, High Pressure Liquid; Edaravone; Reference Standards

1988
Antipyrine metabolism in cultured rat hepatocytes.
    Biochemical pharmacology, 1987, Sep-15, Volume: 36, Issue:18

    Topics: Animals; Antipyrine; Cells, Cultured; Chloramphenicol; Cytochrome P-450 Enzyme Inhibitors; Cytochrome P-450 Enzyme System; Edaravone; Isoenzymes; Kinetics; Liver; Male; Rats; Rats, Inbred Strains

1987
The effect of verapamil on antipyrine pharmacokinetics and metabolism in man.
    British journal of clinical pharmacology, 1986, Volume: 21, Issue:6

    Topics: Adult; Antipyrine; Drug Interactions; Edaravone; Half-Life; Humans; Kinetics; Male; Metabolic Clearance Rate; Verapamil

1986
Antipyrine clearance and metabolism in patients with psoriasis.
    British journal of clinical pharmacology, 1986, Volume: 22, Issue:4

    Topics: Aged; Aged, 80 and over; Antipyrine; Aryl Hydrocarbon Hydroxylases; Edaravone; Female; Half-Life; Humans; Male; Middle Aged; Psoriasis; Saliva; Smoking

1986
The pharmacokinetics of mefloquine in man: lack of effect of mefloquine on antipyrine metabolism.
    British journal of clinical pharmacology, 1985, Volume: 20, Issue:5

    Topics: Adult; Antimalarials; Antipyrine; Chromatography, High Pressure Liquid; Drug Interactions; Edaravone; Humans; Kinetics; Male; Mefloquine; Metabolic Clearance Rate; Quinolines; Saliva

1985
Correlation between antipyrine metabolite formation and theophylline metabolism in humans after simultaneous single-dose administration and at steady state.
    The Journal of pharmacology and experimental therapeutics, 1985, Volume: 233, Issue:3

    Topics: Adult; Antipyrine; Half-Life; Humans; Kinetics; Male; Metabolic Clearance Rate; Theophylline

1985
Antipyrine metabolite formation and excretion in patients with chronic renal failure.
    European journal of clinical pharmacology, 1985, Volume: 28, Issue:5

    Topics: Adult; Aged; Antipyrine; Edaravone; Female; Half-Life; Humans; Kidney Failure, Chronic; Kinetics; Male; Middle Aged; Time Factors

1985
Antipyrine metabolism during hepatic regeneration in the rat.
    Liver, 1985, Volume: 5, Issue:4

    Topics: Animals; Antipyrine; Edaravone; Female; Liver Diseases; Liver Regeneration; Organ Size; Rats; Rats, Inbred Strains; Time Factors

1985
Quantitation and urinary pattern of 4,4'-dihydroxy-antipyrine, 4-hydroxy-antipyrine and 3-hydroxymethyl-antipyrine, as main metabolites of antipyrine in man and rat.
    The Journal of pharmacy and pharmacology, 1982, Volume: 34, Issue:3

    Topics: Adult; Animals; Antipyrine; Biotransformation; Chromatography, Thin Layer; Drug Stability; Glucuronates; Humans; Hydroxylation; Kinetics; Male; Rats; Rats, Inbred Strains

1982
Influence of alaproclate on antipyrine metabolite formation in man.
    European journal of clinical pharmacology, 1984, Volume: 27, Issue:4

    Topics: Adult; Alanine; Antipyrine; Biotransformation; Cytochrome P-450 Enzyme System; Edaravone; Half-Life; Humans; Liver; Male; Oxidation-Reduction

1984
Sources of interindividual variations in acetaminophen and antipyrine metabolism.
    Clinical pharmacology and therapeutics, 1984, Volume: 36, Issue:4

    Topics: Acetaminophen; Administration, Oral; Adolescent; Adult; Antipyrine; Biotransformation; Chromatography, High Pressure Liquid; Environment; Female; Half-Life; Humans; Kinetics; Male; Pregnancy; Twins; Twins, Dizygotic; Twins, Monozygotic

1984
Influence of 9-hydroxyellipticine and 3-methylcholanthrene treatment on antipyrine metabolite formation in rats in vivo.
    Xenobiotica; the fate of foreign compounds in biological systems, 1983, Volume: 13, Issue:4

    Topics: Alkaloids; Animals; Antipyrine; Edaravone; Ellipticines; Kinetics; Methylcholanthrene; Rats; Rats, Inbred Strains

1983
Cimetidine-induced reduction in gastrointestinal absorption of antipyrine and rate constants for formation of its metabolites.
    Clinical pharmacology and therapeutics, 1984, Volume: 35, Issue:5

    Topics: Adult; Antipyrine; Cimetidine; Drug Interactions; Humans; Intestinal Absorption; Kinetics; Male

1984
Monogenic control of variations in antipyrine metabolite formation. New polymorphism of hepatic drug oxidation.
    The Journal of clinical investigation, 1983, Volume: 71, Issue:6

    Topics: Adolescent; Adult; Antipyrine; Genotype; Humans; Kinetics; Liver; Middle Aged; Pedigree; Phenotype; Polymorphism, Genetic; Statistics as Topic

1983
Automated high-performance liqiud chromatographic method for the determination of antipyrine and its metabolites in urine. Some preliminary results obtained from smokers and non-smokers.
    Journal of chromatography, 1982, Sep-10, Volume: 231, Issue:2

    Topics: Adult; Antipyrine; Autoanalysis; Chromatography, High Pressure Liquid; Edaravone; Female; Humans; Male; Smoking

1982
Simultaneous determination of antipyrine, 4-hydroxyantipyrine, 3-hydroxymethylantipyrine and norantipyrine in urine by gas chromatography chemical ionization mass spectrometry.
    Biomedical mass spectrometry, 1982, Volume: 9, Issue:10

    Topics: Antipyrine; Edaravone; Gas Chromatography-Mass Spectrometry; Humans; Reference Standards; Time Factors

1982
A radiometric high-pressure liquid chromatography assay for the simultaneous determination of the three main oxidative metabolites of antipyrine in studies in vitro.
    Analytical biochemistry, 1981, May-15, Volume: 113, Issue:2

    Topics: Animals; Antipyrine; Chromatography, High Pressure Liquid; Edaravone; Gas Chromatography-Mass Spectrometry; Humans; Male; Microsomes, Liver; Rats

1981
Antipyrine clearance and metabolite excretion in patients with chronic hepatitis C.
    Journal of hepatology, 1995, Volume: 22, Issue:1

    Topics: Adult; Antipyrine; Chronic Disease; Edaravone; Female; Hepatitis C; Humans; Male; Middle Aged; Reference Values

1995
Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation.
    Clinical pharmacology and therapeutics, 1996, Volume: 59, Issue:6

    Topics: Anti-Inflammatory Agents, Non-Steroidal; Antipyrine; Autoantibodies; Biotransformation; Catalysis; Cytochrome P-450 Enzyme Inhibitors; Cytochrome P-450 Enzyme System; Edaravone; Gas Chromatography-Mass Spectrometry; Humans; Microsomes, Liver

1996
Effect of age on the pharmacokinetics of antipyrine in calves.
    Research in veterinary science, 1996, Volume: 60, Issue:3

    Topics: Aging; Animals; Antipyrine; Cattle; Edaravone; Female; Half-Life; Metabolic Clearance Rate; Time Factors

1996
Identification of the human hepatic cytochromes P450 involved in the in vitro oxidation of antipyrine.
    Drug metabolism and disposition: the biological fate of chemicals, 1996, Volume: 24, Issue:4

    Topics: Antipyrine; Cytochrome P-450 CYP1A2; Cytochrome P-450 Enzyme Inhibitors; Cytochrome P-450 Enzyme System; Edaravone; Enzyme Inhibitors; Humans; Isoenzymes; Microsomes, Liver; Oxidoreductases; Regression Analysis

1996
Pharmacokinetics of antipyrine in calves after intravenous and oral administration.
    Journal of veterinary pharmacology and therapeutics, 1996, Volume: 19, Issue:5

    Topics: Administration, Oral; Animals; Anti-Inflammatory Agents, Non-Steroidal; Antipyrine; Cattle; Chromatography, High Pressure Liquid; Dose-Response Relationship, Drug; Edaravone; Female; Free Radical Scavengers; Half-Life; Injections, Intravenous; Regression Analysis

1996
The effect of cimetidine on antipyrine metabolism in calves.
    Journal of veterinary pharmacology and therapeutics, 1997, Volume: 20, Issue:1

    Topics: Administration, Oral; Animals; Animals, Newborn; Anti-Inflammatory Agents, Non-Steroidal; Anti-Ulcer Agents; Antipyrine; Cattle; Chromatography, High Pressure Liquid; Cimetidine; Drug Interactions; Edaravone; Female; Free Radical Scavengers; Histamine H2 Antagonists; Software

1997
Determination of antipyrine and metabolites in plasma of a patient with mild renal failure.
    Therapeutic drug monitoring, 1997, Volume: 19, Issue:6

    Topics: Adult; Anti-Inflammatory Agents, Non-Steroidal; Antipyrine; Chromatography, High Pressure Liquid; Edaravone; Female; Humans; Hypertension; Kidney Failure, Chronic; Metabolic Clearance Rate; Reference Values

1997
The effect of age and sex on metabolism and urinary excretion of antipyrine.
    The journals of gerontology. Series A, Biological sciences and medical sciences, 1998, Volume: 53, Issue:1

    Topics: Administration, Oral; Adult; Aged; Aged, 80 and over; Aging; Anti-Inflammatory Agents, Non-Steroidal; Antipyrine; Body Weight; Edaravone; Female; Free Radical Scavengers; Half-Life; Humans; Kidney; Male; Metabolic Clearance Rate; Saliva; Sex Characteristics

1998
Physical exercise and improvement of liver oxidative metabolism in the elderly.
    European journal of applied physiology, 2000, Volume: 81, Issue:1-2

    Topics: Aged; Aging; Antipyrine; Female; Half-Life; Humans; Kidney; Liver; Middle Aged; Oxidation-Reduction; Physical Exertion; Saliva

2000
Effect of experimental fasciolosis on antipyrine metabolism and clearance in water buffaloes.
    Veterinary parasitology, 2000, Mar-01, Volume: 88, Issue:3-4

    Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Antibodies, Helminth; Antipyrine; Aspartate Aminotransferases; Buffaloes; Chromatography, High Pressure Liquid; Edaravone; Enzyme-Linked Immunosorbent Assay; Fascioliasis; Feces; gamma-Glutamyltransferase; Half-Life; Male; Parasite Egg Count

2000