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トラザミド

Tolazamide

HCID 5503
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
1156-19-0
標準SMILES
Cc1ccc(S(=O)(=O)NC(=O)NN2CCCCCC2)cc1
InChIKey
OUDSBRTVNLOZBN-UHFFFAOYSA-N
分子式
C14H21N3O3S
平均分子量
311.4 g/mol
単同位体質量
311.13036271

概要

Tolazamide appears as white to off-white crystalline powder. Odorless or with a slight odor. (NTP, 1992)

名称と識別子

優先名称
Tolazamide
IUPAC
1-(azepan-1-yl)-3-(4-methylphenyl)sulfonylurea
現地名
トラザミド
英語名
Tolazamide
分子式
C14H21N3O3S
分子量
311.4

名称と別名

tolazamide1156-19-0TolinaseNorglycinTolanaseTolazolamideDiabewasTolazamidaTolazamidum1-(Hexahydro-1-azepinyl)-3-p-tolylsulfonylureaNSC-707621-(Hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea
名称をさらに表示
トルアザミドトリナーゼトリナースノルグリシン1-(ヘキサヒドロ-1H-アゼピン-1-イル)-3-(p-トリルスルホニル)尿素トロナーゼトラゾラミドN-[[(ヘキサヒドロ-1H-アゼピン-1-イル)アミノ]カルボニル]-4-メチルベンゼンスルホンアミドジアベワストラザミドトラザミド (JP17)1-(アゼパン-1-イル)-3-(4-メチルベンゼンスルホニル)尿素Tolonaseolazamide
U-17835N-(p-Toluenesulfonyl)-N'-hexamethyleniminoureaNCI-C033274-(p-Tolylsulfonyl)-1,1-hexamethylenesemicarbazideU 17835N-(azepan-1-ylcarbamoyl)-4-methylbenzenesulfonamideCCRIS 591DTXSID3021358

データベース識別子

CAS
1156-19-0
PubChem CID
5503

物性

構造計算による物性

XLogP
1.5
極性表面積
86.9 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
3
重原子数
21
形式電荷
0
複雑度
431

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 3 件

log Kow= 2.69

2.5

2.34

OdorODORLESS OR HAS SLIGHT ODOR
Color/Form · 2 件

Crystals

WHITE TO OFF-WHITE, CRYSTALLINE POWDER

Solubility · 4 件

less than 1 mg/mL at 77 °F (NTP, 1992)

VERY SLIGHTLY SOL IN WATER; FREELY SOL IN CHLOROFORM; SOL IN ACETONE; SIGHTLY SOL IN ALCOHOL

In water, 65.4 mg/l @ 30 °C

3.08e-01 g/L

Human Drugs · 3 件

Breast Feeding; Lactation; Milk, Human; Hypoglycemic Agents; Sulfonylurea Compounds

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Melting Point · 4 件

322 to 336 °F (with decomposition) (NTP, 1992)

170-173 °C

170-173 °C

170 - 173 °C

Physical Description · 2 件

Tolazamide appears as white to off-white crystalline powder. Odorless or with a slight odor. (NTP, 1992)

Solid

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Danger

H370 (50%): Causes damage to organs [Danger Specific target organ toxicity, single exposure]

P260, P264, P270, P308+P316, P321, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.

危険有害性情報

Other Safety InformationIMAP assessments - Benzenesulfonamide, N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methyl-: Human health tier I assessment
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health Hazards · 1 件

SYMPTOMS: Symptoms of exposure to this compound may include nausea, vomiting, epigastric pain, dizziness, weakness, paresthesia, sensitivity reactions such as fever, eosinophilia, jaundice and skin rashes, blood disorders such as leukopenia, thrombocytopenia, aplastic anemia and agranulocytosis, and intolerance to alcohol (with facial flushing). Hypoglycemia can also occur. Hematological disorders include pancytopenia and hemolytic anemia. Photosensitivity, hemorrhage, increased serum alkaline phosphatase and cholestatic jaundice have been reported. Other symptoms may include heartburn, fatigue, malaise and allergic skin reactions which include pruritis, erythema, urticaria and morbilliform or maculopapular eruptions.

FDA Requirements · 1 件

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Reactive Group

化学と産業

薬理情報

ATC Code · 2 件

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1 件

Tolazamide is an oral blood glucose lowering drug of the sulfonylurea class. Tolazamide appears to lower the blood glucose acutely by stimulating the release of insulin from the pancreas, an effect dependent upon functioning beta cells in the pancreatic islets. The mechanism by which tolazamide lowers blood glucose during long-term administration has not been clearly established. With chronic administration in Type II diabetic patients, the blood glucose lowering effect persists despite a gradual decline in the insulin secretory response to the drug. Extrapancreatic effects may be involved in the mechanism of action of oral sulfonylurea hypoglycemic drugs. Some patients who are initially responsive to oral hypoglycemic drugs, including tolazamide, may become unresponsive or poorly responsive over time. Alternatively, tolazamide may be effective in some patients who have become unresponsive to one or more other sulfonylurea drugs. In addition to its blood glucose lowering actions, tolazamide produces a mild diuresis by enhancement of renal free water clearance.

Mechanism of Action · 3 件

Sulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin.

Sulfonylureas are now...thought to act by a number of different mechanisms. 1. ...produce a depolarization of the pancreatic islet beta cell membrane potassium ion permeability. This results in a release of preformed insulin into the circulation and occurs mostly in non-insulin dependent diabetics. 2. ...reduce basal glucose output from the liver... 3. increase insulin receptor binding... 4. ...increasing intracellular levels of AMP... 5. increase insulin secretion by suppressing the release of glucagon and somatostatin from alpha and delta pancreatic cells. /Sulfonylureas/

Sulfonylureas lower blood glucose in NIDDM by directly stimulating the acute release of insulin from functioning beta cells of pancreatic islet tissue by an unknown process that involves a sulfonylurea receptor on the beta cell. Sulfonylureas inhibit the ATP potassium channels on the beta cell membrane and potassium efflux, which results in depolarization and calcium influx, calcium-calmodulin binding, kinase activation, and release of insulin containing granules by exocytosis, an effect similar to that of glucose. Insulin is a hormone that lowers blood glucose and controls the storage and metabolism of carbohydrates, proteins, and fats. Therefore, sulfonylureas are effective only in patients whose pancreata are capable of producing insulin. /Sulfonylurea antidiabetic agents/

関連反応

0 件
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現在のフィルター条件では反応記録がありません。

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
DTXSID
DTXSID3021358
ChEMBL
CHEMBL817
ChEBI
CHEBI:9613
UNII
9LT1BRO48Q
EC Number
214-588-3
Nikkaji
J3.663C
Dissociation Constants
PKA @ 25 °C, 3.6; PKA @ 37.5 °C, 5.68
Collision Cross Section · 3 件

175.4 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID3021358]

173.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

159.41 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
162 · 162-164°C
沸点
300 °C · 300°C (rough estimate)
比重(密度)
1.2228 · 1.2228 (rough estimate)
屈折率
1.674 · 1.6740 (estimate)
貯蔵温度
Sealed in dry,Room Temperature
溶解性
水に極めて溶けにくく、クロロホルムに溶けやすく、アセトンに溶けやすく、エタノールに溶けにくい (96%)。
酸解離定数(Pka)
3.6 · 3.6(at 25℃)
外見
個体
色
ホワイトからオフホワイト
水溶解度
65.4 mg/L · 65.4mg/L(30℃)
主な用途
医薬品（低分子化合物）
InChI
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)
InChIKey
OUDSBRTVNLOZBN-UHFFFAOYSA-N
SMILES
C1(S(NC(NN2CCCCCC2)=O)(=O)=O)=CC=C(C)C=C1
CAS データベース
1156 · 1156-19-0(CAS DataBase Reference)
EPAの化学物質情報
Tolazamide (1156-19-0)

化学的性質

化学的特性White Solid

Amides and Imides
Special ReportsDHEW/NCI; Bioassay of Tolazamide for Possible Carcinogenicity (1978) Technical Rpt Series No. 51 DHEW Pub No. (NIH) 78-1756
Reactivity Profile · 1 件

TOLAZAMIDE is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This chemical is incompatible with acids. (NTP, 1992).

Air and Water ReactionsThis chemical may be sensitive to prolonged exposure to air. Insoluble in water.
Hazard Classes and CategoriesSTOT SE 1 (50%)

安全と保護具

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 件

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal Protective Equipment (PPE) · 1 件

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

毒性情報

Interactions · 5 件

DRUGS THAT MAY INCR RISK OF HYPOGLYCEMIA FROM SULFONYL UREAS INCL OTHER HYPOGLYCEMIC AGENTS, SULFONAMIDES, PROPRANOLOL, SALICYLATES, PHENYLBUTAZONE, PROBENECID, DICUMAROL, CHLORAMPHENICOL, MONOAMINE OXIDASE INHIBITORS, & ALCOHOL. /SULFONYLUREAS/

...TOLAZAMIDE...MAY INTERACT WITH GUANETHIDINE...

HYPOGLYCEMIC ACTIVITY OF CHLORPROPAMIDE MAY BE ENHANCED BY CONCURRENT ADMIN OF CLOFIBRATE. ... SULFONYLUREAS...TOLAZAMIDE...DEMONSTRATED SIMILAR INTERACTION WITH CLOFIBRATE. HALOFENATE...WAS REPORTED TO ENHANCE HYPOGLYCEMIC EFFECT OF SULFONYLUREAS TO GREATER DEGREE THAN CLOFIBRATE.

ISONIAZID MAY INCR BLOOD GLUCOSE LEVELS & IMPAIR GLUCOSE TOLERANCE. ... PRECAUTIONS ARE INDICATED WHEN ISONIAZID IS ADMIN TO DIABETIC PT TREATED BY...ORAL HYPOGLYCEMICS (EG, SULFONYLUREAS...).

For more Interactions (Complete) data for TOLAZAMIDE (25 total), please visit the HSDB record page.

Exposure RoutesRapidly and well absorbed from the gastrointestinal tract.
Toxicity Summary · 1 件

Sulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin.

Signs and SymptomsOverdosage of sulfonylureas can produce hypoglycemia. Severe hypoglycemic reactions with coma, seizure, or other neurological impairment occur infrequently, but constitute medical emergencies requiring immediate hospitalization.
Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=1156-19-0]

Human Toxicity Excerpts · 2 件

HYPOGLYCEMIC REACTIONS, INCL COMA, MAY OCCUR. ...SEVERAL FATALITIES HAVE BEEN REPORTED.

Coma or altered mental status is generally the most important presenting sign in the majority (90%) of patients who have ingested excessive doses of the sulfonylureas ... /Sulfonylurea/

Carcinogen Classification · 6 件

Tolazamide

TR-051: Bioassay of Tolazamide for Possible Carcinogenicity (CASRN 1156-19-0) (1978 )

03/06/78

No Evidence

No Evidence

No Evidence

Drug Induced Liver Injury · 6 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Tolazamide

vLess-DILI-concern

2

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

National Toxicology Program Studies · 1 件

A bioassay of ... tolazamide for possible carcinogenicity was conducted by administering the test chemical in feed to Fischer 344 rats and B6C3F1 mice. Groups of 35 rats and 35 mice of each sex were administered /the test cmpd/ at one of two doses, either 5,000 or 10,000 ppm for 103 wk. Matched controls consisted of 15 rats and 15 mice of each sex. All surviving rats and mice were /sacrificed/ at 104 or 105 wk. Survival rates of the dosed rats of each sex were higher than those for the matched controls and were adequate for the development of late appearing tumors. Survival rates for the mice were lower than those for the rats, particularly for the dosed females (matched controls 67%, low dose 34%, high dose 32%). However, a large number of these deaths in the dosed females occurred after 90 wk on study, and survival of both males and females was adequate for the development of late appearing tumors. All observed tumors were of types commonly found in the strains of animals used, and there were no statistically significant incr in the incidence of tumors in dosed animals as compared with controls. It is concluded that under the conditions of this bioassay, tolazamide was not carcinogenic for Fischer 344 rats or B6C3F1 mice. Levels of Evidence of Carcinogenicity: Male Rats: Negative; Female Rats: Negative; Male Mice: Negative; Female Mice: Negative.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

法規制情報

FDA Requirements · 1 件

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

安全データ

wgk
3
rtecs
YT4400000
毒性
LD50 in rats, mice (mg/kg): >5000 orally, 2239 i.p. (Dulin)
hs_code
2935904000
risk_code
22
hazard_code
Xn
safety_code
36
ストレージクラス
11 - Combustible Solids
有毒物質データの
1156-19-0(Hazardous Substances Data)
Biological Half-Life · 4 件

The average biological half-life of the drug is 7 hours.

PLASMA T/2 IS ABOUT 7 HR...

AVG BIOLOGICAL HALF LIFE...IS 7 HR.

Half-life...7 /hours/ /from table/

Metabolism/Metabolites · 6 件

Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0 to 70%.

TOLAZAMIDE IS METABOLIZED TO A NUMBER OF HYPOGLYCEMIC SUBSTANCES...

Sulfonylureas are rapidly absorbed from the gastrointestinal tract, transported in the blood in highly protein-bound complexes, and subjected to extensive hepatic metabolism (except for chlorpropamide). Wide variation exists among the sulfonylureas in hepatic metabolism and remnal clearance, factors that tend to alter the steady-state serum levels. Metabolites may be active, so there may be a variation between the plasma half-life of the parent drug and the degree of hypoglycemia encountered. /Sulfonylurea/

Active metabolites may accumulate in renal failure. /from table/

Although the exact metabolic fate of tolazamide has not been clearly established, the drug is metabolized, probably in the liver, to two hydroxymetabolites, p-toluenesulfonamide, p-carboxytolazamide, and an unidentified metabolite; several of these metabolites are pharmacologically active. Tolazamide is excreted in urine principally as metabolites; small amounts are excreted in urine unchanged.

Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0 to 70%. Route of Elimination: Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0% to 70%. They are excreted principally in the urine. Half Life: The average biological half-life of the drug is 7 hours.

FDA Pharmacological Classification · 5 件

9LT1BRO48Q

TOLAZAMIDE

Established Pharmacologic Class [EPC] - Sulfonylurea

Chemical Structure [CS] - Sulfonylurea Compounds

Tolazamide is a Sulfonylurea.

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Absorption, Distribution and Excretion · 6 件

Rapidly and well absorbed from the gastrointestinal tract.

Tolazamide is metabolized to five major metabolites ranging in hypoglycemic activity from 0% to 70%. They are excreted principally in the urine.

AFTER ORAL ADMIN PEAK PLASMA LEVELS REACH PEAK IN 4-8 HR.

TOLAZAMIDE IS SLOWLY ABSORBED; ONSET OF HYPOGLYCEMIC ACTION OCCURS @ 4-6 HR & PERSISTS @ SIGNIFICANT LEVEL UP TO 15 HR AFTER SINGLE DOSE. TOLAZAMIDE IS METABOLIZED TO NUMBER OF HYPOGLYCEMIC SUBSTANCES THAT ARE LARGELY EXCRETED BY KIDNEY.

Some metabolites with moderate activity excreted via kidney. /from table/

Excreted (percentage)...85-95 /from table/

Cellular LocationsMembrane

用途と製造

Uses · 3 件

Therap cat: Antidiabetic

An orally effective hypoglycemic drug.

For use as an adjunct to diet to lower the blood glucose in patients with non-insulin dependent diabetes mellitus (Type II) whose hyperglycemia cannot be satisfactorily controlled by diet alone.

Methods of Manufacturing · 2 件

Prepn: Wright, Willette, J Med Pharm Chem 5, 815 (1962); Wright, British patent 887,886 (1962 to Upjohn).

METHYL P-TOLYLSULFONYLCARBAMATE IS CAUSED TO UNDERGO AMMONOLYSIS TYPE OF REACTION WITH 1-AMINOHEXAMETHYLENEIMINE, US PATENT 3,063,903.

Formulations/Preparations... usually administered in a daily dose of 100 to 250 mg, while 750 to 1000 mg is maximal.
応用分野 · 4 件

用途糖尿病の基礎研究。

説明Tolazamide is a first generation sulfonylurea that inhibits sulfonylurea receptor 1 (SUR1) linked to the inwardly rectifying potassium channel (KIR6.2; IC50 = 4.2 μM in HEK293 cells transfected with the human receptor). It has no effect on glucose uptake in L6 rat skeletal muscle cells when used at a concentration of 0.6 mg/mL but enhances glucose uptake two-fold when used in combination with insulin. In vivo, tolazamide (128 mg/kg) reduces glomerulosclerosis and albumin excretion in a rat model of insulin-dependent diabetes induced by streptozotocin . Formulations containing tolazamide have been used in the treatment of type 2 diabetes.

使用Labelled Tolazamide, an antidiabetic.

一般的な説明Tolazamide is N-[[(hexahydro-1H-azepin-1-yl)amino]carbonyl]-4-methylbenzenesulfonamide; or 1-(hexahydro-1H-azepin-1-yl)-3-(p-tolylsulfonyl)urea; or 1-(4-methylphenylsulfonyl)-3-(hexahydro-1H-azepin-1-yl)urea (generic).Tolazamide incorporates a fully saturated azepine moietythat is but weakly basic, with a pKa of～3.32 The pKa of thesulfonylurea group lies within the typical range; thus, inareas of the duodenum wherein the pH falls within the rangeof 4 to 5, the uncharged form of the drug is the predominantspecies, and its lipophilicity lends to rapid absorption bypassive diffusion.

上流・下流製品情報

上流原料

水素化リチウムアルミニウムヘキサメチレンイミン亜硝酸ナトリウム

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補足説明

定義ChEBI: An N-sulfonylurea that is 1-tosylurea in which a hydrogen attached to the nitrogen at position 3 is replaced by an azepan-1-yl group. A hypoglycemic agent, it is used for the treatment of type 2 diabetes mellitus.