WordNet
- a drug (trade name Tolinase) used in treating stable adult-onset diabetes mellitus (同)Tolinase
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/09/09 11:33:09」(JST)
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Tolazamide
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Systematic (IUPAC) name |
N-[(azepan-1-ylamino)carbonyl]-4-methylbenzenesulfonamide |
Clinical data |
AHFS/Drugs.com |
monograph |
MedlinePlus |
a682482 |
Licence data |
US FDA:link |
Pregnancy cat. |
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Legal status |
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Routes |
Oral |
Pharmacokinetic data |
Bioavailability |
? |
Metabolism |
metabolized in the liver to active metabolites |
Half-life |
7 hours |
Excretion |
Renal (85%) and fecal (7%) |
Identifiers |
CAS number |
1156-19-0 |
ATC code |
A10BB05 |
PubChem |
CID 5503 |
DrugBank |
DB00839 |
ChemSpider |
5302 Y |
UNII |
9LT1BRO48Q Y |
KEGG |
D00379 Y |
ChEBI |
CHEBI:9613 |
ChEMBL |
CHEMBL817 Y |
Chemical data |
Formula |
C14H21N3O3S |
Mol. mass |
311.401 g/mol |
SMILES
- O=S(=O)(c1ccc(cc1)C)NC(=O)NN2CCCCCC2
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InChI
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InChI=1S/C14H21N3O3S/c1-12-6-8-13(9-7-12)21(19,20)16-14(18)15-17-10-4-2-3-5-11-17/h6-9H,2-5,10-11H2,1H3,(H2,15,16,18) Y
Key:OUDSBRTVNLOZBN-UHFFFAOYSA-N Y
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Y (what is this?) (verify) |
Tolazamide is an oral blood glucose lowering drug used for people with Type 2 diabetes. It is part of the sulfonylurea family (ATC A10BB).
Synthesis
para-Toluenesulfonamide is converted to its carbamate with ethyl chloroformate in the presence of a base. Heating that intermediate with azepane leads to the displacement of the ethoxy group and the formation of tolazemide:[1]
References
- ^ Wright, J. B.; Willette, R. E. (1962). J. Med. Chem. 5 (4): 815–822. doi:10.1021/jm01239a016.
External links
Oral anti-diabetic drugs and Insulin analogs (A10)
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Insulin |
Sensitizers
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Biguanides
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- Metformin#
- Buformin‡
- Phenformin‡
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TZDs/"glitazones" (PPAR)
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- Pioglitazone
- Rivoglitazone†
- Rosiglitazone
- Troglitazone‡
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Dual PPAR agonists
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- Aleglitazar†
- Muraglitazar§
- Saroglitazar
- Tesaglitazar§
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Secretagogues
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K+ ATP
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Sulfonylureas
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- 1st generation: Acetohexamide
- Carbutamide
- Chlorpropamide
- Metahexamide
- Tolbutamide
- Tolazamide
2nd generation: Glibenclamide (Glyburide)#
- Glibornuride
- Glipizide
- Gliquidone
- Glisoxepide
- Glyclopyramide
- Glimepiride
- Gliclazide
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Meglitinides/"glinides"
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- Nateglinide
- Repaglinide
- Mitiglinide
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GLP-1 agonists
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- Exenatide
- Liraglutide
- Taspoglutide†
- Albiglutide†
- Lixisenatide
- Dulaglutide†
- Semaglutide
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DPP-4 inhibitors
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- Alogliptin
- Anagliptin
- Gemigliptin
- Linagliptin
- Saxagliptin
- Sitagliptin
- Teneligliptin
- Vildagliptin
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GPR40 Free fatty acid receptor 1
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Analogs/other insulins
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- fast-acting (Insulin lispro
- Insulin aspart
- Insulin glulisine)
- short-acting (Regular insulin)
- long-acting (Insulin glargine
- Insulin detemir
- NPH insulin)
- ultra-long-acting (Insulin degludec†)
- inhalable Exubera
- Afrezza
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Other |
Alpha-glucosidase inhibitors
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- Acarbose
- Miglitol
- Voglibose
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Amylin analog
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SGLT2 inhibitors
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- Canagliflozin
- Dapagliflozin
- Empagliflozin†
- Remogliflozin§
- Sergliflozin§
- Tofogliflozin†
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Other
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- Bromocriptine
- Benfluorex‡
- Tolrestat‡
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (d)/cong/tumr, sysi/epon
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proc, drug (A10/H1/H2/H3/H5)
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UpToDate Contents
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English Journal
- Effects of sulfonylureas, alpha-endosulfine counterparts, on glomerulosclerosis in type 1 and type 2 models of diabetes.
- Biederman JI1, Vera E, Rankhaniya R, Hassett C, Giannico G, Yee J, Cortes P.
- Kidney international.Kidney Int.2005 Feb;67(2):554-65.
- BACKGROUND: Previously, we showed the expression of a unique sulfonylurea receptor (SUR) and its putative endogenous ligand, alpha-endosulfine, in mesangial cells and isolated glomeruli. Further, this ligand was up-regulated by high glucose concentration. To investigate the possible role of alpha-en
- PMID 15673303
- Cardiovascular risk factors associated with insulin resistance: effects of oral antidiabetic agents.
- Granberry MC1, Fonseca VA.
- American journal of cardiovascular drugs : drugs, devices, and other interventions.Am J Cardiovasc Drugs.2005;5(3):201-9.
- Patients with type 2 diabetes mellitus have a greater risk of cardiovascular disease than nondiabetic individuals. These patients are often insulin resistant and have an associated clustering of risk factors that contribute to cardiovascular disease. The risk factors include dyslipidemia, hypertensi
- PMID 15901207
- Detection of anti-diabetics in equine plasma and urine by liquid chromatography-tandem mass spectrometry.
- Ho EN1, Yiu KC, Wan TS, Stewart BD, Watkins KL.
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.J Chromatogr B Analyt Technol Biomed Life Sci.2004 Nov 5;811(1):65-73.
- AIM: Anti-diabetics such as sulfonylurea and thiazolidinedione derivatives are hypoglycemic drugs used for the treatment of diabetes. However, they can also be used as a stopper in horseracing. This paper describes a convenient method for the separation and simultaneous detection of 10 anti-diabetic
- PMID 15458724
Japanese Journal
- Influence of Blood Proteins on Biomedical Analysis. IX. : Protective Effects of Human Serum Proteins on Anion-Induced Degradation of Gliclazide
- 小林 邦夫,井垣 歩,木村 正子,迫口 孝文,下沢 充子,松岡 瑛
- Chemical & pharmaceutical bulletin 34(7), 2957-2962, 1986-07-25
- … Other sulfonylureas, tolazamide and glycopyramide, were also degraded in the presence of chloride ion, but tolbutamide, acetohexamide, chlorpropamide and glibenclamide were not. …
- NAID 110003626488
- Influence of Blood Proteins on Biomedical Analysis. V. Effect of Ethyl Alcohol on Gliclazide-binding with Bovine Serum Albumin
- 小林 邦夫,木村 正子,迫口 孝文,長谷 歩,松岡 瑛
- Chemical & pharmaceutical bulletin 30(3), 1077-1080, 1982-03-25
- … The ratio of D_f/D_t of tolubutamide, glyclazide, acetohexamide and glycopyramide with BSA was raised (+Δ2.1-19.8%) in each case, whereas that of chlorpropamide or tolazamide was lowered (-Δ2.9-6.2%) by the addition of ethyl alcohol. …
- NAID 110003634399
- Permeation of Sulfonylureas through Cellulose and Dimethylpolysiloxane Membranes
- 上田 晴久,南部 直樹,永井 恒司
- Chemical & pharmaceutical bulletin 29(4), 1140-1146, 1981-04-25
- … In the case of dimethylpolysiloxane membrane, at pH 2,the permeability constants, P, of tolbutamide, chlorpropamide, glyclopyramide and tolazamide were 16.15,5.13,2.33 and 0.95×10^<-8> …
- NAID 110003633791
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