G-29701 (BioDeep_00001867698)

Main id: BioDeep_00000001814

 

PANOMIX_OTCML-2023


代谢物信息卡片


oxyphenbutazone

化学式: C19H20N2O3 (324.147385)
中文名称: 羟保松
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCCCC1C(=O)N(N(C1=O)C2=CC=C(C=C2)O)C3=CC=CC=C3
InChI: InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3

描述信息

A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.
M - Musculo-skeletal system > M02 - Topical products for joint and muscular pain > M02A - Topical products for joint and muscular pain > M02AA - Antiinflammatory preparations, non-steroids for topical use
M - Musculo-skeletal system > M01 - Antiinflammatory and antirheumatic products > M01A - Antiinflammatory and antirheumatic products, non-steroids > M01AA - Butylpyrazolidines
S - Sensory organs > S01 - Ophthalmologicals > S01B - Antiinflammatory agents > S01BC - Antiinflammatory agents, non-steroids
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D000893 - Anti-Inflammatory Agents
D018501 - Antirheumatic Agents
Oxyphenbutazone is a Phenylbutazone (HY-B0230) metabolite, with anti-inflammatory effect. Oxyphenbutazone is an orally active non-selective COX inhibitor. Oxyphenbutazone selectively kills non-replicating Mycobaterium tuberculosis[1][2].

同义名列表

3 个代谢物同义名

oxyphenbutazone; G-29701; Oxyphenbutazone



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Corinne Vanucci-Bacqué, Florence Bedos-Belval. Anti-inflammatory activity of naturally occuring diarylheptanoids - A review. Bioorganic & medicinal chemistry. 2021 02; 31(?):115971. doi: 10.1016/j.bmc.2020.115971. [PMID: 33422907]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Shakir Saleem, Ruqaiyah Khan, Muhammad Afzal, Imran Kazmi. Oxyphenbutazone promotes cytotoxicity in rats and Hep3B cellsvia suppression of PGE2 and deactivation of Wnt/β-catenin signaling pathway. Molecular and cellular biochemistry. 2018 Jul; 444(1-2):187-196. doi: 10.1007/s11010-017-3243-2. [PMID: 29204817]
  • Joe O Boison, Patricia Dowling, Johanna L Matus, Jana Kinar, Ron Johnson. The Analysis of Phenylbutazone and Its Active Metabolite, Oxyphenbutazone, in Equine Tissues (Muscle, Kidney, and Liver), Urine, and Serum by LC-MS/MS. Journal of AOAC International. 2017 Jul; 100(4):1110-1122. doi: 10.5740/jaoacint.16-0127. [PMID: 28145218]
  • Joe O Boison, Trisha Dowling, Ron Johnson, Jana Kinar. Analysis of phenylbutazone residues in horse tissues with and without enzyme-hydrolysis by LC-MS/MS. Drug testing and analysis. 2016 May; 8(5-6):535-8. doi: 10.1002/dta.2020. [PMID: 27443208]
  • Youwen You, Cornelius E Uboh, Lawrence R Soma, Fuyu Guan, Xiaoqing Li, Jeffrey A Rudy, Jinwen Chen. Screening, quantification, and confirmation of phenylbutazone and oxyphenbutazone in equine plasma by liquid chromatography-tandem mass spectrometry. Journal of analytical toxicology. 2009 Jan; 33(1):41-50. doi: 10.1093/jat/33.1.41. [PMID: 19161668]
  • Takamitsu Kosa, Koji Nishi, Toru Maruyama, Norifumi Sakai, Naoko Yonemura, Hiroshi Watanabe, Ayaka Suenaga, Masaki Otagiri. Structural and ligand-binding properties of serum albumin species interacting with a biomembrane interface. Journal of pharmaceutical sciences. 2007 Nov; 96(11):3117-24. doi: 10.1002/jps.20887. [PMID: 17979211]
  • G Colmenarejo, A Alvarez-Pedraglio, J L Lavandera. Cheminformatic models to predict binding affinities to human serum albumin. Journal of medicinal chemistry. 2001 Dec; 44(25):4370-8. doi: 10.1021/jm010960b. [PMID: 11728183]
  • N S Matthews, K E Peck, T S Taylor, K L Mealey. Pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in miniature donkeys. American journal of veterinary research. 2001 May; 62(5):673-5. doi: 10.2460/ajvr.2001.62.673. [PMID: 11341383]
  • E Grippa, L Santini, G Castellano, M T Gatto, M G Leone, L Saso. Simultaneous determination of hydrocortisone, dexamethasone, indomethacin, phenylbutazone and oxyphenbutazone in equine serum by high-performance liquid chromatography. Journal of chromatography. B, Biomedical sciences and applications. 2000 Jan; 738(1):17-25. doi: 10.1016/s0378-4347(99)00478-8. [PMID: 10778922]
  • M V Jaraiz, C Rodriguez, M D San Andres, F Gonzalez, M I San Andres. Disposition and tolerance of suxibuzone in horses. Equine veterinary journal. 1999 Sep; 31(5):411-6. doi: 10.1111/j.2042-3306.1999.tb03841.x. [PMID: 10505957]
  • Z Cheng, Q McKeller, A Nolan. Pharmacokinetic studies of flunixin meglumine and phenylbutazone in plasma, exudate and transudate in sheep. Journal of veterinary pharmacology and therapeutics. 1998 Aug; 21(4):315-21. doi: 10.1046/j.1365-2885.1998.00144.x. [PMID: 9731955]
  • Y Matsushita, H Gouda, H Tsujishita, S Hirono. Determination of binding conformations of drugs to human serum albumin by transferred nuclear overhauser effect measurements and conformational analyses using high-temperature molecular dynamics calculations. Journal of pharmaceutical sciences. 1998 Mar; 87(3):379-86. doi: 10.1021/js970173v. [PMID: 9523993]
  • R A Sams, D F Gerken, T M Dyke, S M Reed, S M Ashcraft. Pharmacokinetics of intravenous and intragastric cimetidine in horses. I. Effects of intravenous cimetidine on pharmacokinetics of intravenous phenylbutazone. Journal of veterinary pharmacology and therapeutics. 1997 Oct; 20(5):355-61. doi: 10.1046/j.1365-2885.1997.00083.x. [PMID: 9350255]
  • A Haque, J T Stewart. Direct injection HPLC method for the determination of phenylbutazone and oxyphenylbutazone in serum using a semipermeable surface column. Journal of pharmaceutical and biomedical analysis. 1997 Oct; 16(2):287-93. doi: 10.1016/s0731-7085(97)00041-1. [PMID: 9408846]
  • I A Wasfi, A H Abdel Hadi, O Zorob, Osman M al-G, N S Boni. Pharmacokinetics of phenylbutazone in camels. American journal of veterinary research. 1997 Jun; 58(6):636-40. doi: NULL. [PMID: 9185972]
  • A Kadir, B H Ali, G al Hadrami, A K Bashir, M F Landoni, P Lees. Phenylbutazone pharmacokinetics and bioavailability in the dromedary camel (Camelus dromedarius). Journal of veterinary pharmacology and therapeutics. 1997 Feb; 20(1):54-60. doi: 10.1046/j.1365-2885.1997.04427.x. [PMID: 9049950]
  • Z Cheng, E Welsh, A Nolan, Q A McKellar. Pharmacokinetic and pharmacodynamic studies on phenylbutazone and oxyphenbutazone in goats. The Veterinary record. 1997 Jan; 140(2):40-3. doi: 10.1136/vr.140.2.40. [PMID: 9123796]
  • B C Sallustio, B A Fairchild, P R Pannall. Interaction of human serum albumin with the electrophilic metabolite 1-O-gemfibrozil-beta-D-glucuronide. Drug metabolism and disposition: the biological fate of chemicals. 1997 Jan; 25(1):55-60. doi: NULL. [PMID: 9010630]
  • K L Mealey, N S Matthews, K E Peck, A C Ray, T S Taylor. Comparative pharmacokinetics of phenylbutazone and its metabolite oxyphenbutazone in clinically normal horses and donkeys. American journal of veterinary research. 1997 Jan; 58(1):53-5. doi: NULL. [PMID: 8989496]
  • P C Mills, J C Ng, D E Auer. The effect of inflammation on the disposition of phenylbutazone in thoroughbred horses. Journal of veterinary pharmacology and therapeutics. 1996 Dec; 19(6):475-81. doi: 10.1111/j.1365-2885.1996.tb00085.x. [PMID: 8971677]
  • K E Peck, A C Ray, G Manuel, M M Rao, J Foos. Quantification of phenylbutazone in equine sera by use of high-performance liquid chromatography with a nonevaporative extraction technique. American journal of veterinary research. 1996 Nov; 57(11):1522-4. doi: NULL. [PMID: 8915422]
  • P Claeson, U Pongprayoon, T Sematong, P Tuchinada, V Reutrakul, P Soontornsaratune, W C Taylor. Non-phenolic linear diarylheptanoids from Curcuma xanthorrhiza: a novel type of topical anti-inflammatory agents: structure-activity relationship. Planta medica. 1996 Jun; 62(3):236-40. doi: 10.1055/s-2006-957867. [PMID: 8693036]
  • L M Neto, M H Andraus, M C Salvadori. Determination of phenylbutazone and oxyphenbutazone in plasma and urine samples of horses by high-performance liquid chromatography and gas chromatography-mass spectrometry. Journal of chromatography. B, Biomedical applications. 1996 Apr; 678(2):211-8. doi: 10.1016/0378-4347(95)00508-0. [PMID: 8738024]
  • P C Mills, J C Ng, J Hrdlicka, D E Auer. Disposition and urinary excretion of phenylbutazone in normal and febrile greyhounds. Research in veterinary science. 1995 Nov; 59(3):261-6. doi: 10.1016/0034-5288(95)90014-4. [PMID: 8588103]
  • P C Mills, J C Ng, K V Skelton, A A Seawright, D E Auer. Phenylbutazone in racing greyhounds: plasma and urinary residues 24 and 48 hours after a single intravenous administration. Australian veterinary journal. 1995 Aug; 72(8):304-8. doi: 10.1111/j.1751-0813.1995.tb03560.x. [PMID: 8579562]
  • B R Simmons, N K Jagota, J T Stewart. A supercritical fluid chromatographic method using packed columns for phenylbutazone and oxyphenbutazone in serum, and for phenylbutazone in a dosage form. Journal of pharmaceutical and biomedical analysis. 1995 Jan; 13(1):59-64. doi: 10.1016/0731-7085(95)90652-k. [PMID: 7718635]
  • J Landuyt, F T Delbeke, M Debackere. The intramuscular bioavailability of a phenylbutazone preparation in the horse. Journal of veterinary pharmacology and therapeutics. 1993 Dec; 16(4):494-500. doi: 10.1111/j.1365-2885.1993.tb00216.x. [PMID: 8126767]
  • J R Wilcke, M V Crisman, R A Sams, D F Gerken. Pharmacokinetics of phenylbutazone in neonatal foals. American journal of veterinary research. 1993 Dec; 54(12):2064-7. doi: NULL. [PMID: 8116939]
  • F T Delbeke, L Vynckier, M Debackere. The disposition of suxibuzone in the horse. Journal of veterinary pharmacology and therapeutics. 1993 Sep; 16(3):283-90. doi: 10.1111/j.1365-2885.1993.tb00175.x. [PMID: 8230399]
  • M C Caturla, E Cusido. Solid-phase extraction for the high-performance liquid chromatographic determination of indomethacin, suxibuzone, phenylbutazone and oxyphenbutazone in plasma, avoiding degradation of compounds. Journal of chromatography. 1992 Oct; 581(1):101-7. doi: 10.1016/0378-4347(92)80452-v. [PMID: 1429991]
  • B Desfosses, C Nicot, M Waks. A drug release-facilitating mechanism for human serum albumin in reverse micelles: requirement of a structural switch. Biochemistry international. 1992 Feb; 26(2):257-64. doi: NULL. [PMID: 1558538]
  • B Desfosses, N Cittanova, W Urbach, M Waks. Ligand binding at membrane mimetic interfaces. Human serum albumin in reverse micelles. European journal of biochemistry. 1991 Jul; 199(1):79-87. doi: 10.1111/j.1432-1033.1991.tb16094.x. [PMID: 1712302]
  • C D Gaitonde, P V Pathak. Estimation of the analgesic muscle relaxants chlorzoxazone and diazepam in human plasma by reversed-phase liquid chromatography. Journal of chromatography. 1990 Jun; 528(2):407-14. doi: 10.1016/s0378-4347(00)82398-1. [PMID: 2384578]
  • M Tariq, A M Ageel, M A al-Yahya, J S Mossa, M S al-Said. Anti-inflammatory activity of Teucrium polium. International journal of tissue reactions. 1989; 11(4):185-8. doi: ". [PMID: 2634627]
  • J H Dröge, L H Janssen, J Wilting. The fatty-acid-induced conformational states of human serum albumin investigated by means of multiple co-binding of protons and oleic acid. The Biochemical journal. 1988 Mar; 250(2):443-6. doi: 10.1042/bj2500443. [PMID: 2833243]
  • P Lees, T Ayliffe, T E Maitho, J B Taylor. Pharmacokinetics, metabolism and excretion of phenylbutazone in cattle following intravenous, intramuscular and oral administration. Research in veterinary science. 1988 Jan; 44(1):57-67. doi: 10.1016/0034-5288(88)90014-8. [PMID: 3375589]
  • J Dawson, P Lees, A D Sedgwick. Actions of non-steroidal anti-inflammatory drugs on equine leucocyte movement in vitro. Journal of veterinary pharmacology and therapeutics. 1987 Jun; 10(2):150-9. doi: 10.1111/j.1365-2885.1987.tb00092.x. [PMID: 3612943]
  • P Lees, J B Taylor, T E Maitho, J D Millar, A J Higgins. Metabolism, excretion, pharmacokinetics and tissue residues of phenylbutazone in the horse. The Cornell veterinarian. 1987 Apr; 77(2):192-211. doi: . [PMID: 3568689]
  • W E Woods, T Weckman, J W Blake, T Tobin. Effects of phenylbutazone and oxyphenbutazone on acidic drug detection in high performance thin layer chromatographic systems. Journal of pharmacological methods. 1986 Dec; 16(4):297-313. doi: 10.1016/0160-5402(86)90033-1. [PMID: 3784574]
  • T C Pinkerton, J A Perry, J D Rateike. Separation of furosemide, phenylbutazone and oxyphenbutazone in plasma by direct injection onto internal surface reversed-phase columns with systematic optimization of selectivity. Journal of chromatography. 1986 Oct; 367(2):412-8. doi: 10.1016/s0021-9673(00)94862-3. [PMID: 3782354]
  • P Lees, A J Higgins, I C Mawhinney, D S Reid. Absorption of phenylbutazone from a paste formulation administered orally to the horse. Research in veterinary science. 1986 Sep; 41(2):200-6. doi: 10.1016/s0034-5288(18)30599-x. [PMID: 3775111]
  • M J Franssen, Y Tan, I Freij, C A Van Ginneken, F W Gribnau. Specimen handling in an HPLC determination of phenylbutazone and its major metabolites in plasma, avoiding degradation of the compounds. Pharmaceutisch weekblad. Scientific edition. 1986 Aug; 8(4):229-33. doi: 10.1007/bf01957783. [PMID: 3763367]
  • P Lees, J B Taylor, A J Higgins, S C Sharma. Phenylbutazone and oxyphenbutazone distribution into tissue fluids in the horse. Journal of veterinary pharmacology and therapeutics. 1986 Jun; 9(2):204-12. doi: 10.1111/j.1365-2885.1986.tb00031.x. [PMID: 3723663]
  • J H Dröge, L H Janssen, J Wilting. Evidence for the fatty acid-induced heterogeneity of the N and B conformations of human serum albumin. Biochemical pharmacology. 1985 Sep; 34(18):3299-304. doi: 10.1016/0006-2952(85)90349-1. [PMID: 4038338]
  • V K Deshmukh, P H Raman, J N Dhuley, S R Naik. Role of ceruloplasmin in inflammation: increased serum ceruloplasmin levels during inflammatory conditions and its possible relationship with anti-inflammatory agents. Pharmacological research communications. 1985 Jul; 17(7):633-42. doi: 10.1016/0031-6989(85)90070-0. [PMID: 4048245]
  • W E Woods, S Chay, T Houston, J W Blake, T Tobin. Effects of phenylbutazone and oxyphenbutazone on basic drug detection in high performance thin layer chromatographic systems. Journal of veterinary pharmacology and therapeutics. 1985 Jun; 8(2):181-9. doi: 10.1111/j.1365-2885.1985.tb00942.x. [PMID: 2862290]
  • T Houston, S Chay, W E Woods, G Combs, S Kamerling, J W Blake, A G Edmundson, R Vessiney, T Tobin. Phenylbutazone and its metabolites in plasma and urine of thoroughbred horses: population distributions and effects of urinary pH. Journal of veterinary pharmacology and therapeutics. 1985 Jun; 8(2):136-49. doi: 10.1111/j.1365-2885.1985.tb00937.x. [PMID: 4020945]
  • R Gronwall, G Price. Estimation of urine flow rate in mares. American journal of veterinary research. 1985 May; 46(5):1107-10. doi: NULL. [PMID: 4003886]
  • L R Soma, R Sams, W Duer, T Tobin, C Woodward, J McDonald. Plasma and serum concentrations of phenylbutazone and oxyphenbutazone in racing Thoroughbreds 24 hours after treatment with various dosage regimens. American journal of veterinary research. 1985 Apr; 46(4):932-8. doi: NULL. [PMID: 4014842]
  • P Lees, T E Maitho, J B Taylor. Pharmacokinetics of phenylbutazone in two age groups of ponies: a preliminary study. The Veterinary record. 1985 Mar; 116(9):229-32. doi: 10.1136/vr.116.9.229. [PMID: 4002593]
  • J H Dröge, L H Janssen, J Wilting. A study on the allosteric interaction between the major binding sites of human serum albumin using microcalorimetry. Biochimica et biophysica acta. 1985 Mar; 827(3):396-402. doi: 10.1016/0167-4838(85)90224-9. [PMID: 3970944]
  • J M Bailey, J Butler. Anti-inflammatory drugs in experimental atherosclerosis. Part 6. Combination therapy with steroid and non-steroid agents. Atherosclerosis. 1985 Feb; 54(2):205-12. doi: 10.1016/0021-9150(85)90179-0. [PMID: 3986018]
  • S Chay, W E Woods, T E Nugent, T Weckman, T Houston, F Sprinkle, J W Blake, T Tobin, L R Soma, J Yocum. Population distributions of phenylbutazone and oxyphenbutazone after oral and i.v. dosing in horses. Journal of veterinary pharmacology and therapeutics. 1984 Dec; 7(4):265-76. doi: 10.1111/j.1365-2885.1984.tb00911.x. [PMID: 6512917]
  • S Cronberg, E Wallmark, I Söderberg. Effect on platelet aggregation of oral administration of 10 non-steroidal analgesics to humans. Scandinavian journal of haematology. 1984 Aug; 33(2):155-9. doi: 10.1111/j.1600-0609.1984.tb02390.x. [PMID: 6474093]
  • A J Higgins, P Lees, J B Taylor. Influence of phenylbutazone on eicosanoid levels in equine acute inflammatory exudate. The Cornell veterinarian. 1984 Jul; 74(3):198-207. doi: NULL. [PMID: 6587959]
  • N Loubaris, A Michel, G Cros, J J Serrano, S Katz, M Boucard. Circadian changes in carrageenin-induced edema: the anti-inflammatory effect and bioavailability of phenylbutazone in rats. Life sciences. 1984 Jun; 34(24):2379-84. doi: 10.1016/0024-3205(84)90425-9. [PMID: 6727571]
  • S Okonek, H J Reinecke. Acute toxicity of pyrazolones. The American journal of medicine. 1983 Nov; 75(5A):94-8. doi: 10.1016/0002-9343(83)90238-3. [PMID: 6359872]
  • L R Soma, D E Gallis, W L Davis, T A Cochran, C B Woodward. Phenylbutazone kinetics and metabolite concentrations in the horse after five days of administration. American journal of veterinary research. 1983 Nov; 44(11):2104-9. doi: NULL. [PMID: 6650958]
  • T Houston, T Tobin, J W Blake. Effect of urine pH on urine levels of oxyphenbutazone in racing horses. Drug metabolism and disposition: the biological fate of chemicals. 1983 Nov; 11(6):617-9. doi: NULL. [PMID: 6140151]
  • J H Dröge, L H Janssen, J Wilting. Allosteric properties of the oxyphenbutazone--human serum albumin complex. Pharmaceutisch weekblad. Scientific edition. 1983 Oct; 5(5):228-33. doi: 10.1007/bf02332949. [PMID: 6646989]
  • J O Minta, M B Urowitz, H A Smythe, D E Isenman. Effect on the human complement system of the major non-steroidal anti-inflammatory drugs: aspirin, indomethacin, phenylbutazone, oxyphenbutazone and sulindac. Clinical and experimental immunology. 1983 Sep; 53(3):555-61. doi: . [PMID: 6616956]
  • A Sioufi, D Colussi, P Mangoni. Determination of oxyphenbutazone in human plasma by high-performance liquid chromatography. Journal of chromatography. 1983 Jun; 275(1):201-5. doi: 10.1016/s0378-4347(00)84362-5. [PMID: 6874865]
  • P Queneau, M Ollagnier, H Decousus, B Perpoint, J L Brazier, L Faucon. [Influence of tobacco on the serum levels and pharmacokinetics of phenylbutazone and oxyphenbutazone]. Revue du rhumatisme et des maladies osteo-articulaires. 1983 Apr; 50(4):293-7. doi: . [PMID: 6879097]
  • W Pruzanski, S Saito, G DeBoer. Modulation of phagocytosis and bactericidal activity of human polymorphonuclear and mononuclear phagocytes by antiarthritic agents. The Journal of rheumatology. 1983 Apr; 10(2):197-203. doi: NULL. [PMID: 6864673]
  • S Somasundaram, J Sadique, A Subramoniam. Influence of extra-intestinal inflammation on the in vitro absorption of 14C-glucose and the effects of anti-inflammatory drugs in the jejunum of rats. Clinical and experimental pharmacology & physiology. 1983 Mar; 10(2):147-52. doi: 10.1111/j.1440-1681.1983.tb00180.x. [PMID: 6872332]
  • P G Milhaud, T Faure, J Chaintreuil, J M Cathala, B Lebleu. Responses to interferon of LM cells growing continuously in the absence of serum and exogenous lipids. The Journal of general virology. 1983 Feb; 64 (Pt 2)(?):485-9. doi: 10.1099/0022-1317-64-2-485. [PMID: 6187895]
  • A Gaucher, P Netter, G Faure, J P Schoeller, A Gerardin. Diffusion of oxyphenbutazone into synovial fluid, synovial tissue, joint cartilage and cerebrospinal fluid. European journal of clinical pharmacology. 1983; 25(1):107-12. doi: 10.1007/bf00544025. [PMID: 6617711]
  • M Ollagnier, P Queneau, J F Latour, J L Brazier, H Decousus, G Faucon. [Reduction of plasma concentrations of phenylbutazone and oxyphenbutazone in smokers]. Therapie. 1982 Sep; 37(5):549-56. doi: NULL. [PMID: 7179323]
  • A Abd Elbary, J J Vallner, C W Whitworth. Effect of albumin conformation on binding of phenylbutazone and oxyphenbutazone to human serum albumin. Journal of pharmaceutical sciences. 1982 Feb; 71(2):241-4. doi: 10.1002/jps.2600710225. [PMID: 7062254]
  • E L Gerring, P Lees, J B Taylor. Pharmacokinetics of phenylbutazone and its metabolites in the horse. Equine veterinary journal. 1981 Jul; 13(3):152-7. doi: 10.1111/j.2042-3306.1981.tb03472.x. [PMID: 7297544]
  • W Lehmann, H J Wintzer, H H Frey. [Kinetics of anti-inflammatory drugs in serum and synovia of horses (author's transl)]. DTW. Deutsche tierarztliche Wochenschrift. 1981 Jun; 88(6):218-20. doi: NULL. [PMID: 7026207]
  • J L Vila-Jato, J Areses, A Concheiro. [Determination of paracetamol and oxyphenbutazone in plasma by high pressure liquid chromatography]. Bollettino chimico farmaceutico. 1981 Mar; 120(3):165-71. doi: NULL. [PMID: 7272020]
  • H Spahn, E Mutschler. [Determination of bumadizone, phenylbutazone and oxyphenbutazone in human plasma by high-performance liquid chromatography (author's transl)]. Arzneimittel-Forschung. 1981; 31(3):495-9. doi: NULL. [PMID: 6894379]
  • H Spahn, E Mutschler, H E Geissler, G Faust-Tinnefeldt. [Comparison of bumadizone-, phenylbutazone- and oxyphenbutazone-plasma levels after a single oral dose of phenylbutazone and of bumadizone, respectively (author's transl)]. Arzneimittel-Forschung. 1981; 31(3):499-503. doi: NULL. [PMID: 6894380]
  • M Held, G Scheible. [Interactions of phenylbutazone and oxyphenbutazone with glymidine (author's transl)]. Arzneimittel-Forschung. 1981; 31(6):1036-8. doi: NULL. [PMID: 6455124]
  • L F Prescott, J A Critchley, M Balali-Mood. Phenylbutazone overdosage: abnormal metabolism associated with hepatic and renal damage. British medical journal. 1980 Oct; 281(6248):1106-7. doi: 10.1136/bmj.281.6248.1106. [PMID: 7427601]
  • R Dugal, C Dupuis, M Bertrand, M A Gagnon. The effect of buffering on oxyphenbutazone absorption kinetics and systemic availability. Biopharmaceutics & drug disposition. 1980 Oct; 1(6):307-21. doi: 10.1002/bdd.2510010603. [PMID: 7459426]
  • T Marunaka, T Shibata, Y Minami, Y Umeno. Simultaneous determination of phenylbutazone and its metabolites in plasma and urine by high-performance liquid chromatography. Journal of chromatography. 1980 Sep; 183(3):331-8. doi: 10.1016/s0378-4347(00)81713-2. [PMID: 7419650]
  • D R Varma. Influence of dietary portein on the disposition and metabolism of phenylbutazone in rats. Canadian journal of physiology and pharmacology. 1980 Mar; 58(3):231-6. doi: 10.1139/y80-040. [PMID: 7378926]
  • I Sjöholm, B Ekman, A Kober, I Ljungstedt-Påhlman, B Seiving, T Sjödin. Binding of drugs to human serum albumin:XI. The specificity of three binding sites as studied with albumin immobilized in microparticles. Molecular pharmacology. 1979 Nov; 16(3):767-77. doi: NULL. [PMID: 530258]
  • H E Williamson, G R Gaffney, W A Bourland. Renal actions of oxyphenbutazone. Journal of pharmaceutical sciences. 1979 Sep; 68(9):1178-9. doi: 10.1002/jps.2600680933. [PMID: 501546]
  • W D Wosilait, M P Ryan. The effects of oleic acid, tolbutamide, and oxyphenbutazone on the binding of warfarin by human serum albumin. Research communications in chemical pathology and pharmacology. 1979 Sep; 25(3):577-84. doi: NULL. [PMID: 504792]
  • M Bertrand, C Dupuis, M A Gagnon, R Dugal. Quantitative determination of plasma oxyphenbutazone by gas-liquid chromatography with selective nitrogen detection. Journal of chromatography. 1979 Apr; 171(?):377-83. doi: 10.1016/s0021-9673(01)95318-x. [PMID: 546857]
  • G Raymond, J Toubol, P Pastorini, Y Kermarec, J P Varini, Y Lefichoux, P Dellamonica. [Eosinophilic prostatitis with Oxyuris eggs in the urine (proceedings)]. Journal d'urologie et de nephrologie. 1979 Mar; 85(3):228-30. doi: NULL. [PMID: 573336]
  • U Langness, E Löwensprung. [Proliferation of L 929 mouse fibroblasts and synthesis of active peptidyl prolyl hydroxylase in these cells in monolayer culture under the influence of D-penicillamine, azathioprine, aurothiopolypeptide, oxyphenbutazone and prednisolone (author's transl)]. Research in experimental medicine. Zeitschrift fur die gesamte experimentelle Medizin einschliesslich experimenteller Chirurgie. 1978 Mar; 172(2):193-201. doi: 10.1007/bf01851411. [PMID: 205931]
  • K Raman, S S Parmar, S Kumar, S J Brumleve. Anti-inflammatory and antiproteolytic properties of 2-[acyl-N-(substituted benzylidene)hydrazino]5-phenyltetrazoles. Pharmacology. 1978; 17(1):56-60. doi: 10.1159/000136835. [PMID: 684074]
  • E S Pepper, W D Wosilait. Multiple factors affecting excretion of warfarin in rats. Research communications in chemical pathology and pharmacology. 1977 Oct; 18(2):275-81. doi: . [PMID: 918347]
  • R J Ancill. Plasma exchange in severe rhesus disease. British medical journal. 1977 Jun; 1(6074):1469-70. doi: 10.1136/bmj.1.6074.1469-b. [PMID: 861696]
  • B Album, I Olsen, P Lokken. Bilateral surgical removal of impacted mandibular third molar teeth as a model for drug evaluation: a test with oxyphenbutazone (Tanderil). International journal of oral surgery. 1977 Jun; 6(3):177-89. doi: 10.1016/s0300-9785(77)80051-3. [PMID: 408287]
  • M S Moss. A review of drug 'clearance times' in racehorses. Equine veterinary journal. 1977 Apr; 9(2):53-6. doi: 10.1111/j.2042-3306.1977.tb03978.x. [PMID: 324761]
  • G Baur, H Kurz, H Trunk. Alteration of protein-binding during storage of human plasma preparations. Der Anaesthesist. 1977 Mar; 26(3):148-50. doi: NULL. [PMID: 857693]
  • T Tobin, J W Blake, R Valentine. Drug interactions in the horse: effects of chloramphenicol, quinidine, and oxyphenbutazone on phenylbutazone metabolism. American journal of veterinary research. 1977 Jan; 38(1):123-7. doi: . [PMID: 835859]
  • J Aarbakke, O M Bakke, E J Milde, D S Davies. Disposition and oxidative metabolism of phenylbutazone in man. European journal of clinical pharmacology. 1977; 11(5):359-66. doi: 10.1007/bf00566533. [PMID: 880975]
  • L Arnold, C Collins, G A Starmer. Studies on the modification of renal lesions due to aspirin and oxyphenbutazone in the rat and the effects on the kidney of 2:4 dinitrophenol. Pathology. 1976 Jul; 8(3):179-84. doi: 10.3109/00313027609058995. [PMID: 1004943]
  • J Williamson, A K Sim, J C Chawla, H M Tham, J V Forrester, N V Mammo. Estimation of oxyphenbutazone concentrations in human serum and aqueous humor. Eye, ear, nose & throat monthly. 1976 May; 55(5):176-9. doi: NULL. [PMID: 1269678]
  • J Villiaumey, B Larget-Piet. [Frequency of side effects of pyrazoles]. Therapie. 1976 May; 31(3):299-311. doi: NULL. [PMID: 136763]
  • L Arnold, C Collins, G A Starmer. Further studies of the acute effects of phenylbutazone, oxyphenbutazone and indomethacin on the rat kidney. Pathology. 1976 Apr; 8(2):135-41. doi: 10.3109/00313027609094439. [PMID: 972771]