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ニトロフラントイン

ニトロフラントイン 化学構造式
67-20-9
CAS番号.
67-20-9
化学名:
ニトロフラントイン
别名:
パルフラン;フラントイン;フラダンチン;マクロダンチン;1-(5-ニトロフルフリリデンアミノ)イミダゾリジン-2,4-ジオン;ニトロフラントイン;1-[[(5-ニトロ-2-フラニル)メチレン]アミノ]-2,4-イミダゾリジンジオン;1-[[(5-ニトロ-2-フラニル)メチレン]アミノ]イミダゾリジン-2,4-ジオン;N-トイン;ウレトイン;フラドニン;オラフラン;3-[[(5-ニトロフラン-2-イル)メチレン]アミノ]イミダゾリジン-2,5-ジオン;ダナフル;3-[[(5-ニトロ-2-フリル)メチレン]アミノ]-2,5-ジオキソイミダゾリジン;イツラン;1-[(5-ニトロフルフリリデン)アミノ]ヒダントイン;ニトロフラントイン標準品;ニトロフラントン;ニトロフラントインフラドキシル
英語化学名:
Nitrofurantoin
英語别名:
Upiol;Furina;Ituran;Macpac;Nitoin;Nitrex;N-Toin;Urodin;Cystit;Furalan
CBNumber:
CB7346080
化学式:
C8H6N4O5
分子量:
238.16
MOL File:
67-20-9.mol

ニトロフラントイン 物理性質

融点 :
268°C
沸点 :
380.75°C (rough estimate)
比重(密度) :
1.5824 (rough estimate)
屈折率 :
1.6700 (estimate)
貯蔵温度 :
0-6°C
溶解性:
DMF: soluble50mg/mL
酸解離定数(Pka):
7.2(at 25℃)
外見 :
crystalline
色:
yellow
水溶解度 :
<0.01 g/100 mL at 19 ºC
Sensitive :
Light Sensitive & Hygroscopic
極大吸収波長 (λmax):
358nm(MeOH)(lit.)
Merck :
14,6599
BRN :
893207
安定性::
Stability Stable, but light-sensitive. Combustible. Incompatible with strong oxidizing agents, strong alkalies, strong acids. Decomposes upon contact with most metals other than stainless steel and aluminium.
CAS データベース:
67-20-9(CAS DataBase Reference)
NISTの化学物質情報:
Hydantoin, n-(5-nitro-2-furfurylidene)-1-amino-(67-20-9)
EPAの化学物質情報:
2,4-Imidazolidinedione, 1-[[(5-nitro-2-furanyl)methylene] amino]-(67-20-9)
安全性情報
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn
Rフレーズ  22-42/43
Sフレーズ  22-36/37-45
RIDADR  2811
WGK Germany  3
RTECS 番号 MU2800000
TSCA  Yes
国連危険物分類  6.1(b)
容器等級  III
HSコード  29349990
有毒物質データの 67-20-9(Hazardous Substances Data)
毒性 LD50 oral in rat: 604mg/kg
化審法 (9)-980
絵表示(GHS)
注意喚起語 Danger
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H317 アレルギー性皮膚反応を起こすおそれ 感作性、皮膚 1 警告 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H334 吸入するとアレルギー、喘息または、呼吸困難 を起こすおそれ 感作性、呼吸器 1 危険 P261, P285, P304+P341, P342+P311,P501
注意書き
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P284 呼吸用保護具を着用すること。
P304+P340 吸入した場合:空気の新鮮な場所に移し、呼吸しやすい 姿勢で休息させること。
P342+P311 呼吸に関する症状が出た場合:医師に連絡すること。

ニトロフラントイン 価格 もっと(17)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01AFAB24079 ニトロフラントイン, 98%
Nitrofurantoin, 98%
67-20-9 25g ¥6880 2018-12-26 購入
富士フイルム和光純薬株式会社(wako) W01AFAB24079 ニトロフラントイン, 98%
Nitrofurantoin, 98%
67-20-9 100g ¥23800 2018-12-26 購入
東京化成工業 N0883 ニトロフラントイン >98.0%(HPLC)(T)
Nitrofurantoin >98.0%(HPLC)(T)
67-20-9 25g ¥14000 2018-12-04 購入
関東化学株式会社(KANTO) 49830-19 ニトロフラントイン標準品
Nitrofurantoin standard
67-20-9 250mg ¥8000 2018-12-13 購入
Sigma-Aldrich Japan 46502 ニトロフラントイン VETRANAL?, analytical standard
Nitrofurantoin VETRANAL?, analytical standard
67-20-9 250mg ¥10100 2018-12-25 購入

ニトロフラントイン MSDS


Nitrofurantoin

ニトロフラントイン 化学特性,用途語,生産方法

外観

黄色~黄褐色, 結晶性粉末~粉末

溶解性

N ,N -ジメチルホルムアミドに溶け、水、エタノール及びアセトンにほとんど溶けない。

効能

抗菌薬

化学的特性

lemon yellow crystalline powder

使用

counterirritant

使用

A nitrofuran antibiotic with low resistance potential that is rapidly metabolized by mammals. Active against both Gram-positive and Gram-negative bacteria. Nitrofurantoin is also a prooxidant that is cytotoxic due to the generation of intracellular H2O2. Antibacterial.

定義

ChEBI: An imidazolidine-2,4-dione that is hydantoin substituted at position 1 by a [(5-nitro-2-furyl)methylene]amino group. An antibiotic that damages bacterial DNA.

brand name

Ivadantin (Procter & Gamble);Furan;Nitrofan.

抗菌性

It is active against almost all the common urinary pathogens, except Proteus mirabilis. It is bactericidal.
It antagonizes the activity of nalidixic acid and other quinolones in vitro, but this combination is unlikely to be used clinically.

獲得抵抗性

Surprisingly for an agent that has been used for so long, resistance remains uncommon. R-factor-mediated resistance has been reported, but this appears to be very unusual. The mechanism of resistance seems to be a decreased nitroreductase activity in the target organism.
There is cross-resistance within the nitrofuran group, but none with antibiotics of other chemical classes.

一般的な説明

Odorless lemon yellow crystals or fine yellow powder. Bitter taste.

空気と水の反応

Insoluble in water.

反応プロフィール

Nitrofurantoin is sensitive to light. Nitrofurantoin is incompatible with alkalis. Nitrofurantoin is also incompatible with strong oxidizers and strong acids. Nitrofurantoin decomposes on contact with metals other than stainless steel and aluminum.

危険性

Questionable carcinogen.

火災危険

Flash point data for Nitrofurantoin are not available; however, Nitrofurantoin is probably combustible.

応用例(製薬)

A synthetic compound available only for oral administration. There are three formulations, differing in their crystalline nature: microcrystalline, macrocrystalline, and a delayedrelease preparation containing a combination of the two. The macrocrystalline form is said to be less liable to give rise to the most common adverse event, nausea. However, pharmacokinetic and clinical trial evidence for this assertion is not very strong.
It is slightly soluble in water (c. 200 mg/L) but more so in dilute alkali. Solubility in ethanol is modest (500 mg/L), but the compound dissolves very well in dimethylformamide (80 g/L). If packaged in light-resistant containers and kept at room temperature, it is stable for more than 5 years. The yellow solution should be kept in the dark.

薬物動態学

Oral absorption:>95%
Cmax 100 mg oral: <2 mg/L after 1–4 h
Plasma half-life:0.5–1 h
Volume of distribution: 0.6 L/kg
Plasma protein binding: 60–70%
Absorption
It is absorbed mainly from the proximal small intestine and the plasma peak concentration may not be achieved for as long as 4 h. The recommendation to take the drug with food may be motivated by reducing the incidence of nausea rather than increasing bioavailability.
Bioavailability varies widely between different brands and this may not be apparent from results of standard in-vitro pharmaceutical tests. Therefore, different brands should not be substituted unless therapeutic equivalence has been formally established.
Distribution
Serum levels are low, owing to extensive metabolism and the short plasma half-life. Tissue concentrations are too low for adequate treatment of systemic infection, including pyelonephritis. Negligible concentrations are found in breast milk and only a small amount crosses the placenta.
Metabolism and excretion
About 20% of the dose is excreted in microbiologically active form in the urine, sufficient to give inhibitory concentrations against urinary pathogens for up to 6 h. With reduced renal function (creatinine clearance <60 mL/min), urinary excretion falls, and virtually ceases when creatinine clearance is below 20 mL/min. This gives rise to the risk of accumulation in the blood and inadequate urine levels. With this proviso, it can be given to elderly patients. Infants over the age of 3 months may also be treated, but in the absence of a suitable suspension, and at the recommended dosage, a 6-month baby would need to be given one-tenth of a standard 50 mg tablet.

臨床応用

Acute dysuria and frequency
Bacteriuria in pregnancy
Prophylaxis of recurrent cystitis (reduced dosage)

副作用

Nausea, which may be combined with anorexia or vomiting, or both, occurs in about 30% of patients taking the microcrystalline form, causing about 10% to stop treatment. The frequency of nausea is approximately halved with the macrocrystalline formulation. Nausea is due to a direct effect on the vomiting center; it occurs early in the course, and its incidence may be reduced by taking the medication with food or milk.
Pulmonary, hepatic, neurological and hematological side effects have been reported, but are very uncommon. There are two kinds of pulmonary reaction. Acute reactions are the more common, starting within 5–10 days of the first dose, or within a few hours on re-challenge. Symptoms may resemble those found in asthma, tracheobronchitis or pneumonia, and usually resolve permanently within 2 days. There may be an eosinophilia. Subacute or chronic reactions, often referred to as pneumonitis, are of more gradual onset, and resolve only slowly when the drug is stopped. Prolonged dyspnea and cough may be accompanied by fibrosis.
Hepatic reactions follow prolonged drug usage and usually manifest as chronic active hepatitis, sometimes with cirrhosis. The prognosis is good, but recovery may take months. Peripheral neuropathy has been reported mainly in patients with pre-existing impaired renal function. The prognosis depends upon the severity of the symptoms. Unlike hepatic and pulmonary effects, for which immunological phenomena seem to be responsible, neurological events have been attributed to a direct toxic effect of the drug, one of its metabolites or the superoxide generated in vivo.
In common with other nitrofurans, nitrofurantoin may cause hemolysis in patients who lack glucose-6-phosphate dehydrogenase.

安全性プロファイル

Poison by ingestion and intraperitoneal routes. Human systemic effects: peripheral motor nerve recording changes, ataxia, changes in urine composition, and hemolysis with or without anemia. Human reproductive effects by ingestion: spermatogenesis. An experimental teratogen. Other experimental reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Veterinary Drugs and Treatments

Considered a urinary tract antiseptic, nitrofurantoin is used primarily in small animals, but also occasionally in horses in the treatment of lower urinary tract infections caused by susceptible bacteria. It is not effective in treating renal cortical or perinephric abscesses or other systemic infections.

ニトロフラントイン 上流と下流の製品情報

原材料

準備製品


ニトロフラントイン 生産企業

Global( 203)Suppliers
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67-20-9(ニトロフラントイン)キーワード:


  • 67-20-9
  • 1-(((5-nitro-2-furanyl)methylene)amino)-2,4-imidazolidinedione
  • 1-(5-NITRO-2-FURFURYLIDENEAMINO)HYDANTOIN
  • 1-[(5-nitrofurfurylidene)amino]hydantoin
  • LABOTEST-BB LT00134625
  • FURADOXYL
  • N-(5-NITRO-2-FURFURYLIDENE)-1-AMINOHYDANTOIN
  • NITROFURANTOIN
  • NITROFURANTOINE
  • Furadonin
  • Furadonine
  • Furadontin
  • Furalan
  • Furaloid
  • Furantoin
  • GOINE VETRANAL, 250 MG
  • Nitrofurantoin,98%
  • NITROFURANTOIN,ANHYDROUS,USP
  • nitrofurantonie
  • 1[N-(5-Nitrofur-2-yl)methyleneamino]-imidazolidine-2,4-dione
  • Furadoxyl, N-(5-Nitro-2-furfurylidene)-1-aminohydantoin, Nitrofurantoine
  • 1-[(5-Mitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
  • Danafur
  • Nitrofurantoin,Furadoxyl, N-(5-Nitro-2-furfurylidene)-1-aminohydantoin, Nitrofurantoine
  • Nitrofurantoin (500 mg)
  • 1-(((5-Nitrofuran-2-yl)Methylene)aMino)iMidazolidine-2,4-dione
  • Nitrofurantoi
  • Nitrofurantoin solution, 100ug/ml
  • 1-{[(5-nitro-2-furyl)methylene]amino}-2,4-imidazolidinedione
  • Furatoin
  • Furina
  • パルフラン
  • フラントイン
  • フラダンチン
  • マクロダンチン
  • 1-(5-ニトロフルフリリデンアミノ)イミダゾリジン-2,4-ジオン
  • ニトロフラントイン
  • 1-[[(5-ニトロ-2-フラニル)メチレン]アミノ]-2,4-イミダゾリジンジオン
  • 1-[[(5-ニトロ-2-フラニル)メチレン]アミノ]イミダゾリジン-2,4-ジオン
  • N-トイン
  • ウレトイン
  • フラドニン
  • オラフラン
  • 3-[[(5-ニトロフラン-2-イル)メチレン]アミノ]イミダゾリジン-2,5-ジオン
  • ダナフル
  • 3-[[(5-ニトロ-2-フリル)メチレン]アミノ]-2,5-ジオキソイミダゾリジン
  • イツラン
  • 1-[(5-ニトロフルフリリデン)アミノ]ヒダントイン
  • ニトロフラントイン標準品
  • ニトロフラントン
  • ニトロフラントインフラドキシル
  • ニトロフラントイン, 98%
  • ニトロフラントイン (JAN)
  • 尿路防腐薬
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