acetohexamide (BioDeep_00000413078)

Volatile Flavor Compounds

代谢物信息卡片

acetohexamide

化学式: C15H20N2O4S (324.11437200000006)
中文名称: 乙酰己酰胺
谱图信息: 最多检出来源 Homo sapiens(urine) 35.29%

分子结构信息

SMILES: CC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1
InChI: InChI=1S/C15H20N2O4S/c1-11(18)12-7-9-14(10-8-12)22(20,21)17-15(19)16-13-5-3-2-4-6-13/h7-10,13H,2-6H2,1H3,(H2,16,17,19)

描述信息

A - Alimentary tract and metabolism > A10 - Drugs used in diabetes > A10B - Blood glucose lowering drugs, excl. insulins > A10BB - Sulfonylureas
C78276 - Agent Affecting Digestive System or Metabolism > C29711 - Anti-diabetic Agent > C97936 - Sulfonylurea Antidiabetic Agent
D007004 - Hypoglycemic Agents
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4168; ORIGINAL_PRECURSOR_SCAN_NO 4165
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4170; ORIGINAL_PRECURSOR_SCAN_NO 4165
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4125; ORIGINAL_PRECURSOR_SCAN_NO 4121
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4143; ORIGINAL_PRECURSOR_SCAN_NO 4140
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX506; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4151; ORIGINAL_PRECURSOR_SCAN_NO 4150
ORIGINAL_PRECURSOR_SCAN_NO 4163; CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4165
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4165; ORIGINAL_PRECURSOR_SCAN_NO 4163
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8394; ORIGINAL_PRECURSOR_SCAN_NO 8389
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8413; ORIGINAL_PRECURSOR_SCAN_NO 8409
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8458; ORIGINAL_PRECURSOR_SCAN_NO 8454
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8489; ORIGINAL_PRECURSOR_SCAN_NO 8485
CONFIDENCE standard compound; INTERNAL_ID 894; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8471; ORIGINAL_PRECURSOR_SCAN_NO 8468

同义名列表

2 个代谢物同义名

acetohexamide; Acetohexamide

数据库引用编号

24 个数据库交叉引用编号

ChEBI: CHEBI:28052
KEGG: C06806
KEGGdrug: D00219
PubChem: 1989
DrugBank: DB00414
ChEMBL: CHEMBL1589
MeSH: Acetohexamide
CAS: 968-81-0
MoNA: LU089456
MoNA: LU089455
MoNA: LU089454
MoNA: LU089453
MoNA: LU089452
MoNA: LU089451
MoNA: LU089406
MoNA: LU089405
MoNA: LU089403
MoNA: LU089402
MoNA: LU089401
PubChem: 9025
PDB-CCD: TF9
NIKKAJI: J3.355C
RefMet: Acetohexamide
KNApSAcK: 28052

分类词条

Benzenesulfonyl compounds

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]
Agnieszka Szkudlarek, Michał Wilk, Małgorzata Maciążek-Jurczyk. In Vitro Investigations of Acetohexamide Binding to Glycated Serum Albumin in the Presence of Fatty Acid. Molecules (Basel, Switzerland). 2020 May; 25(10):. doi: 10.3390/molecules25102340. [PMID: 32429512]
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]
Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11. Chemico-biological interactions. 2019 May; 305(?):12-20. doi: 10.1016/j.cbi.2019.03.026. [PMID: 30926317]
Holger Rehmann. Epac2: a sulfonylurea receptor?. Biochemical Society transactions. 2012 Feb; 40(1):6-10. doi: 10.1042/bst20110640. [PMID: 22260657]
Man-Wo Tsang. The management of type 2 diabetic patients with hypoglycaemic agents. ISRN endocrinology. 2012; 2012(?):478120. doi: 10.5402/2012/478120. [PMID: 22645689]
Zenghan Tong, K S Joseph, David S Hage. Detection of heterogeneous drug-protein binding by frontal analysis and high-performance affinity chromatography. Journal of chromatography. A. 2011 Dec; 1218(49):8915-24. doi: 10.1016/j.chroma.2011.04.078. [PMID: 21612784]
Michelle J Yoo, David S Hage. Use of peak decay analysis and affinity microcolumns containing silica monoliths for rapid determination of drug-protein dissociation rates. Journal of chromatography. A. 2011 Apr; 1218(15):2072-8. doi: 10.1016/j.chroma.2010.09.070. [PMID: 20956006]
Sara B G Basiaga, David S Hage. Chromatographic studies of changes in binding of sulfonylurea drugs to human serum albumin due to glycation and fatty acids. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Nov; 878(30):3193-7. doi: 10.1016/j.jchromb.2010.09.033. [PMID: 20974553]
K S Joseph, Jeanethe Anguizola, Abby J Jackson, David S Hage. Chromatographic analysis of acetohexamide binding to glycated human serum albumin. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Oct; 878(28):2775-81. doi: 10.1016/j.jchromb.2010.08.021. [PMID: 20829128]
K S Joseph, David S Hage. Characterization of the binding of sulfonylurea drugs to HSA by high-performance affinity chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jun; 878(19):1590-8. doi: 10.1016/j.jchromb.2010.04.019. [PMID: 20435530]
Yorishige Imamura, Hideaki Shimada. Differential pharmacokinetics of acetohexamide in male Wistar-Imamichi and Sprague-Dawley rats: role of microsomal carbonyl reductase. Biological & pharmaceutical bulletin. 2005 Jan; 28(1):185-7. doi: 10.1248/bpb.28.185. [PMID: 15635190]
Yorishige Imamura, Hideaki Shimada. Strain- and sex-related differences of carbonyl reductase activities in kidney microsomes and cytosol of rats. Journal of applied toxicology : JAT. 2004 Nov; 24(6):437-41. doi: 10.1002/jat.996. [PMID: 15558648]
Yoe-Ray Ku, Li-Yun Chag, Li-Kang Ho, Jer-Huei Lin. Analysis of synthetic anti-diabetic drugs in adulterated traditional Chinese medicines by high-performance capillary electrophoresis. Journal of pharmaceutical and biomedical analysis. 2003 Sep; 33(2):329-34. doi: 10.1016/s0731-7085(03)00287-5. [PMID: 12972099]
Yorishige Imamura, Miho Kaneko, Hidenori Takada, Masaki Otagiri, Hideaki Shimada, Hiroyuki Akita. Sex-dependent pharmacokinetics of S(-)-hydroxyhexamide, a pharmacologically active metabolite of acetohexamide, in rats. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2002 Dec; 133(4):587-92. doi: 10.1016/s1532-0456(02)00177-1. [PMID: 12458186]
Hideaki Shimada, Shizuka Yamaguchi, Hideyuki Murata, Masaki Otagiri, Yorishige Imamura. Cadmium exposure decreases androgen-dependent metabolism of acetohexamide in liver microsomes of male rats through its testicular toxicity. Archives of toxicology. 2002 Feb; 76(1):8-12. doi: 10.1007/s00204-001-0313-7. [PMID: 11875619]
Y Imamura, H Takada, R Kamizono, M Otagiri. Hormonal regulation of male-specific 20beta-hydroxysteroid dehydrogenase with carbonyl reductase-like activity present in kidney microsomes of rats. The Journal of steroid biochemistry and molecular biology. 2001 Oct; 78(4):373-8. doi: 10.1016/s0960-0760(01)00110-8. [PMID: 11717008]
Y Imamura, K Sanai, K Seri, H Akita. Hypoglycemic effect of S(-)-hydroxyhexamide, a major metabolite of acetohexamide, and its enantiomer R(+)-hydroxyhexamide. Life sciences. 2001 Sep; 69(16):1947-55. doi: 10.1016/s0024-3205(01)01284-x. [PMID: 11693275]
K Seri, K Sanai, K Kurashima, Y Imamura, H Akita. (R)-ACX is a novel sufonylurea compound with potent, quick and short-lasting hypoglycemic activity. European journal of pharmacology. 2000 Feb; 389(2-3):253-6. doi: 10.1016/s0014-2999(99)00922-x. [PMID: 10688991]
Y Imamura, M Kaneko, Y Mori, M Otagiri. Sex-dependent pharmacokinetics and in vitro reductive metabolism of acetohexamide in Wistar-Imamichi rats. Biological & pharmaceutical bulletin. 1999 Apr; 22(4):435-8. doi: 10.1248/bpb.22.435. [PMID: 10328570]
H Koyama, N Sugioka, A Uno, S Mori, K Nakajima. Effects of glycosylation of hypoglycaemic drug binding to serum albumin. Biopharmaceutics & drug disposition. 1997 Dec; 18(9):791-801. doi: 10.1002/(sici)1099-081x(199712)18:9<791::aid-bdd66>3.0.co;2-1. [PMID: 9429743]
Y Imamura, T Koga, T Migita, A Ryu, M Otagiri, M Nozawa, H Akita. Characterization of acetohexamide reductases purified from rabbit liver, kidney, and heart: structural requirements for substrates and inhibitors. Journal of biochemistry. 1997 Apr; 121(4):705-10. doi: 10.1093/oxfordjournals.jbchem.a021643. [PMID: 9163521]
Y Imamura, T Koga, T Higuchi, M Otagiri, E Sugino, S Hibino. Inhibitory effect of drugs with a ketone group on reduction of acetohexamide catalyzed by carbonyl reductase from rabbit kidney. Journal of enzyme inhibition. 1997 Feb; 11(4):285-92. doi: 10.3109/14756369709027657. [PMID: 9208371]
T Higuchi, Y Imamura, M Otagiri. Kinetic studies on the reduction of acetohexamide catalyzed by carbonyl reductase from rabbit kidney. Biochimica et biophysica acta. 1993 Aug; 1158(1):23-8. doi: 10.1016/0304-4165(93)90091-l. [PMID: 8353128]
Y Shibutani, T Yokota. A case of acetohexamide-induced hypoglycemia: the influence of hypothyroidism on the metabolism of acetohexamide. Nihon Naibunpi Gakkai zasshi. 1991 Jan; 67(1):42-9. doi: 10.1507/endocrine1927.67.1_42. [PMID: 2013345]
M L Chen, A J Jackson. The role of metabolites in bioequivalency assessment. I. Linear pharmacokinetics without first-pass effect. Pharmaceutical research. 1991 Jan; 8(1):25-32. doi: 10.1023/a:1015865920043. [PMID: 2014204]
Y Imamura, T Nomura, Y Katsuki, Y Kojima, M Otagiri. Mechanism of pharmacodynamic and pharmacokinetic interactions between acetohexamide and phenylbutazone in rabbits. Pharmacology & toxicology. 1990 Nov; 67(5):415-9. doi: 10.1111/j.1600-0773.1990.tb00855.x. [PMID: 2096386]
R Kawamori, K Bando, Y Yamasaki, M Kubota, T Watarai, N Iwama, M Shichiri, T Kamada. Fasting plus prandial insulin supplements improve insulin secretory ability in NIDDM subjects. Diabetes care. 1989 Nov; 12(10):680-5. doi: 10.2337/diacare.12.10.680. [PMID: 2515048]
Y Imamura, H Abe, Y Kojima, M Otagiri. In vivo and in vitro binding of (-)-hydroxyhexamide, a major metabolite of acetohexamide, to rabbit serum. Journal of pharmacobio-dynamics. 1989 Aug; 12(8):503-7. doi: 10.1248/bpb1978.12.503. [PMID: 2614641]
Y Imamura, Y Kojima, M Otagiri. [Metabolic reduction of acetohexamide in rat liver and kidney]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1988 Aug; 108(8):758-62. doi: 10.1248/yakushi1947.108.8_758. [PMID: 3246646]
Y Kojima, Y Imamura, M Otagiri. Metabolic reduction of acetohexamide in rat kidney: sex difference and effect of streptozotocin-induced diabetes. Journal of pharmacobio-dynamics. 1988 May; 11(5):309-13. doi: 10.1248/bpb1978.11.309. [PMID: 2971793]
Y Kojima, Y Imamura, M Otagiri. [Effect of various drugs on the in vitro metabolic reduction of acetohexamide]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1988 Jan; 108(1):66-70. doi: 10.1248/yakushi1947.108.1_66. [PMID: 3385610]
Y Imamura, Y Kojima, M Otagiri. Reduction of acetohexamide by rabbit heart cytosol. Journal of pharmacobio-dynamics. 1986 Jan; 9(1):110-1. doi: 10.1248/bpb1978.9.110. [PMID: 3519920]
Y Imamura, Y Kojima, H Ichibagase. Effect of simultaneous administration of drugs on absorption and excretion. XIX. Binding of acetohexamide and its major metabolite, (-)-hydroxyhexamide, to human serum albumin. Chemical & pharmaceutical bulletin. 1985 Mar; 33(3):1281-4. doi: 10.1248/cpb.33.1281. [PMID: 4028305]
T G Skillman, J M Feldman. The pharmacology of sulfonylureas. The American journal of medicine. 1981 Feb; 70(2):361-72. doi: 10.1016/0002-9343(81)90773-7. [PMID: 6781341]
H A Milman, J C Peckham, J M Ward, R E Tarone. Reduction of the severity of nephropathy in aging Fischer 344 rats treated with analogs of arylsulfonyluria. Toxicology and applied pharmacology. 1979 Jul; 49(3):425-30. doi: 10.1016/0041-008x(79)90442-3. [PMID: 473209]
P Girgis-Takla, I Chroneos. Fluorimetric determination of acetohexamide in plasma and tablet formulations using 1-methylnicotinamide. The Analyst. 1979 Feb; 104(1235):117-23. doi: 10.1039/an9790400117. [PMID: 474978]
S Baba, T Baba, T Iwanaga. Effect of acetohexamide (a sulfonylurea hypoglycemic agent) in blood plasma on creatinine assay in clinical laboratory tests. Chemical & pharmaceutical bulletin. 1979 Jan; 27(1):139-43. doi: 10.1248/cpb.27.139. [PMID: 428022]
W D Black, S R Acchiardo. Acetohexamide hypoglycemia: treatment by peritoneal dialysis. Southern medical journal. 1977 Oct; 70(10):1240-1. doi: . [PMID: 910178]
M H Tan, C A Graham, R F Bradley, R E Gleason, J S Soeldner. The effects of long-term therapy with oral hypoglycemic agents on the oral glucose tolerance test dynamics in male chemical diabetics. Diabetes. 1977 Jun; 26(6):561-70. doi: 10.2337/diab.26.6.561. [PMID: 324835]
J W Kleber, J A Galloway, B E Rodda. GLC determination of acetohexamide and hydroxyhexamide in biological fluids. Journal of pharmaceutical sciences. 1977 May; 66(5):635-8. doi: 10.1002/jps.2600660507. [PMID: 874743]
E Tsalikian, T W Dunphy, N V Bohannon, M Lorenzi, J E Gerich, P H Forsham, J P Kane, J H Karam. The effect of chronic oral antidiabetic therapy on insulin and glucagon responses to a meal. Diabetes. 1977 Apr; 26(4):314-21. doi: 10.2337/diab.26.4.314. [PMID: 849812]
S W Shen, R Bressler. Clinical pharmacology of oral antidiabetic agents (first of two parts). The New England journal of medicine. 1977 Mar; 296(9):493-7. doi: 10.1056/nejm197703032960906. [PMID: 319363]
V A Skoutakis, W D Black, S R Acchiardo, G C Wood. Peritoneal dialysis in the treatment of acetohexamide-induced hypoglycemia. American journal of hospital pharmacy. 1977 Jan; 34(1):68-70. doi: . [PMID: 831475]
G M Fanelli. Urate excretion. Annual review of medicine. 1977; 28(?):349-54. doi: 10.1146/annurev.me.28.020177.002025. [PMID: 324366]
D E Drayer. Pharmacologically active drug metabolites: therapeutic and toxic activities, plasma and urine data in man, accumulation in renal failure. Clinical pharmacokinetics. 1976 Nov; 1(6):426-43. doi: 10.2165/00003088-197601060-00003. [PMID: 799549]
M M Reidenberg. Drug metabolism in uremia. Clinical nephrology. 1975; 4(3):83-5. doi: ". [PMID: 1102176]
Y Maruhama, A Yanbe, R Abe, A Oneda, S Yamagata. Effect of clofibrate administration on plasma post-heparin lipolytic activity in man. The Tohoku journal of experimental medicine. 1974 Aug; 113(4):343-9. doi: 10.1620/tjem.113.343. [PMID: 4446025]
P L Hsu, J K Ma, L A Luzzi. Interactions of sulfonylureas with plasma proteins. Journal of pharmaceutical sciences. 1974 Apr; 63(4):570-3. doi: 10.1002/jps.2600630416. [PMID: 4208196]
R B Tattersall. Mild familial diabetes with dominant inheritance. The Quarterly journal of medicine. 1974 Apr; 43(170):339-57. doi: NULL. [PMID: 4212169]
K Emerson, B N Saxena, S K Varma, E L Poindexter. The caloric cost and sources of energy in diabetic pregnancy. Obstetrics and gynecology. 1974 Mar; 43(3):354-62. doi: NULL. [PMID: 4814453]
A M Moses, J Howanitz, M Miller. Diuretic action of three sulfonylurea drugs. Annals of internal medicine. 1973 Apr; 78(4):541-4. doi: 10.7326/0003-4819-78-4-541. [PMID: 4632790]
J Judis. Displacement of sulfonylureas from human serum proteins by coumarin derivatives and cortical steroids. Journal of pharmaceutical sciences. 1973 Feb; 62(2):232-7. doi: 10.1002/jps.2600620210. [PMID: 4119680]
G D Molnar, W F Taylor, A L Langworthy. Plasma immunoreactive insulin patterns in insulin-treated diabetics. Studies during continuous blood glucose monitoring. Mayo Clinic proceedings. 1972 Oct; 47(10):709-19. doi: NULL. [PMID: 4635563]
J Judis. Binding of sulfonylureas to serum proteins. Journal of pharmaceutical sciences. 1972 Jan; 61(1):89-93. doi: 10.1002/jps.2600610116. [PMID: 5058652]
W Berger, P Spring. [Changes of pharmacokinetics of oral antidiabetics from drug interference and renal insufficiency]. Deutsche medizinische Wochenschrift (1946). 1970 Dec; 95(50):2525-7. doi: 10.1055/s-0028-1108869. [PMID: 5488752]
E J Ariëns. [Oral antidiabetics. Dose, plasma concentration and effect]. Acta diabetologica latina. 1969 Sep; 6 Suppl 1(?):143-76. doi: NULL. [PMID: 4392071]
R Helmi, S A el-Mahdy, H Ali, M A Khayyal. Preliminary report on the hypoglycaemic effect of Trifolium alexandrinum and Lupinus termis in animal and man. The Journal of the Egyptian Medical Association. 1969; 52(7):538-51. doi: ". [PMID: 5365916]
J M Hershman, K Konerding. Effects of sulfonylurea drugs on the thyroid and serum protein binding of thyroxine in the rat. Endocrinology. 1968 Jul; 83(1):74-8. doi: 10.1210/endo-83-1-74. [PMID: 5659433]
T F Yu, L Berger, A B Gutman. Hypoglycemic and uricosuric properties of acetohexamide and hydroxyhexamide. Metabolism: clinical and experimental. 1968 Apr; 17(4):309-16. doi: 10.1016/0026-0495(68)90099-1. [PMID: 5646202]
J Reforzo-Membrives, L I Moledo, A E Lanaro, A Megías. Antidiuretic effect of 1-propyl-3-p-chlorobenzene-sulfonylurea (chlorpropamide). The Journal of clinical endocrinology and metabolism. 1968 Mar; 28(3):332-6. doi: 10.1210/jcem-28-3-332. [PMID: 5644194]
J A Galloway, R E McMahon, H W Culp, F J Marshall, E C Young. Metabolism, blood levels and rate of excretion of acetohexamide in human subjects. Diabetes. 1967 Feb; 16(2):118-27. doi: 10.2337/diab.16.2.118. [PMID: 5334897]
R W Alexander. Prolonged hypoglycemia following acetohexamide administration. Report of two cases with impaired renal function. Diabetes. 1966 May; 15(5):362-4. doi: 10.2337/diab.15.5.362. [PMID: 5936465]
D B Stone, J D Brown. Effect of sulfonylurea drugs on plasma free fatty acid and blood glucose concentrations in man. Diabetes. 1966 May; 15(5):314-8. doi: 10.2337/diab.15.5.314. [PMID: 5936457]
R E McMahon, F J Marshall, H W Culp. The nature of the metabolites of acetohexamide in the rat and in the human. The Journal of pharmacology and experimental therapeutics. 1965 Aug; 149(2):272-9. doi: NULL. [PMID: 5831048]
J SHELDON, J ANDERSON, L STONER. SERUM CONCENTRATION AND URINARY EXCRETION OF ORAL SULFONYLUREA COMPOUNDS: RELATION TO DIABETIC CONTROL. Diabetes. 1965 Jun; 14(?):362-7. doi: 10.2337/diab.14.6.362. [PMID: 14298920]
H G BAUER. SEVERE AND PROLONGED HYPOGLYCEMIC SHOCK DURING SULFONYLUREA TREATMENT. Metabolism: clinical and experimental. 1965 Mar; 14(?):220-8. doi: 10.1016/0026-0495(65)90062-4. [PMID: 14261406]
D L SMITH, T J VECCHIO, A A FORIST. METABOLISM OF ANTIDIABETIC SULFONYLUREAS IN MAN. I. BIOLOGICAL HALF-LIVES OF THE P-ACETYLBENZENESULFONYLUREAS, U-18536 AND ACETOHEXAMIDE AND THEIR METABOLITES. Metabolism: clinical and experimental. 1965 Mar; 14(?):229-40. doi: 10.1016/0026-0495(65)90063-6. [PMID: 14261407]
O LOZANO CASTANEDA, R A CAMERINI D AVALOS, L P KRALL, A MARBLE. TWO YEARS' EXPERIENCE WITH ACETOHEXAMIDE. Metabolism: clinical and experimental. 1964 Feb; 13(?):99-106. doi: 10.1016/0026-0495(64)90123-4. [PMID: 14127093]