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フラゾリドン

フラゾリドン 化学構造式
67-45-8
CAS番号.
67-45-8
化学名:
フラゾリドン
别名:
ネフチン;フロキソン;3-(5-ニトロフルフリリデンアミノ)-4,5-ジヒドロオキサゾール-2(3H)-オン;3-(5-ニトロフルフリリデンアミノ)-2-オキサゾリジノン;フロキサン;3-[[(5-ニトロフラン-2-イル)メチレン]アミノ]オキサゾリジン-2-オン;ニフリドン;フラゾリドン標準品;3-[(5-ニトロフルフリリデン)アミノ]-2-オキサゾリジノン;フラゾリドン
英語化学名:
Furazolidone
英語别名:
Furox;Neftin;NF 180;nf-180;Furall;Furaxon;Furazol;Furazon;Furidon;Furovag
CBNumber:
CB8452405
化学式:
C8H7N3O5
分子量:
225.16
MOL File:
67-45-8.mol

フラゾリドン 物理性質

融点 :
254-256°C (dec.)
沸点 :
366.66°C (rough estimate)
比重(密度) :
1.5406 (rough estimate)
屈折率 :
1.7180 (estimate)
闪点 :
2 °C
貯蔵温度 :
Keep in dark place,Sealed in dry,Room Temperature
溶解性:
formic acid: soluble50mg/mL
酸解離定数(Pka):
-1.98±0.20(Predicted)
外見 :
powder
色:
yellow
極大吸収波長 (λmax):
365nm(DMSO)(lit.)
Sensitive :
Light Sensitive
Merck :
14,4300
BRN :
8317414
安定性::
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey:
PLHJDBGFXBMTGZ-UITAMQMPSA-N
IARC:
3 (Vol. 31, Sup 7) 1987
NISTの化学物質情報:
Furazolidone(67-45-8)
EPAの化学物質情報:
Furazolidone (67-45-8)
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,F
Rフレーズ  62-40-36-20/21/22-11-68
Sフレーズ  36-22-36/37-16
WGK Germany  3
RTECS 番号 RQ3675000
TSCA  Yes
HSコード  29349990
有毒物質データの 67-45-8(Hazardous Substances Data)
化審法 (9)-991
絵表示(GHS)
注意喚起語 Warning
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
H303 飲み込むと有害のおそれ 急性毒性、経口 5 P312
H341 遺伝性疾患のおそれの疑い 生殖細胞変異原性 2 警告 P201,P202, P281, P308+P313, P405,P501
H361 生殖能または胎児への悪影響のおそれの疑い 生殖毒性 2 警告 P201, P202, P281, P308+P313, P405,P501
注意書き
P201 使用前に取扱説明書を入手すること。
P202 全ての安全注意を読み理解するまで取り扱わないこ と。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P281 指定された個人用保護具を使用すること。
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
P405 施錠して保管すること。

フラゾリドン 価格 もっと(13)

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) W01MPB02193465 フラゾリドン
Furazolidone
67-45-8 1g ¥9100 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01MPB02193465 フラゾリドン
Furazolidone
67-45-8 5g ¥12900 2021-03-23 購入
東京化成工業 F0821 フラゾリドン >98.0%(HPLC)
Furazolidone >98.0%(HPLC)
67-45-8 25g ¥12800 2021-03-23 購入
関東化学株式会社(KANTO) 16115-96 フラゾリドン標準品 >99.5%(HLC)
Furazolidone standard >99.5%(HLC)
67-45-8 500mg ¥5100 2021-03-23 購入
Sigma-Aldrich Japan PHR2598
67-45-8 500MG ¥23500 2021-03-23 購入

フラゾリドン 化学特性,用途語,生産方法

外観

黄色, 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、水にほとんど溶けない。

用途

フラゾリドンは細菌や原虫感染による下痢や腸炎の治療に使用される。 フラゾリドンは養殖業で使用される。

効能

抗菌薬, 抗原虫薬

説明

Furazolidone belongs to the group of nitro furans. This antimicrobal (antibacterial and antiprotozoal) agent is used in veterinary medicine both topically and orally, particularly in animal feed. Reactions have been reported in workers exposed to it by contact with animal feed. Cross reactions with other nitrofuran derivatives are rare.

化学的特性

solid

Originator

Tricofuron,Norwich Eaton,US,1955

使用

The minimum inhibitory concentration of furazolidone was assessed to study the nonreplicating persistence of M. tuberculosis in aerobic and anaerobic conditions using luminescence-based low-oxygen-recovery assay.

使用

Antimicrobial.

使用

Antiprotozoal; antibacterial

定義

ChEBI: A member of the class of oxazolidines that is 1,3-oxazolidin-2-one in which the hydrogen attached to the nitrogen is replaced by an N-{[(5-nitro-2-furyl)methylene]amino} group. It has antibacterial and antiprotozoal properties, and is us d in the treatment of giardiasis and cholera.

Manufacturing Process

In 212 cc of water are mixed 21.2 grams (0,112 mol) of N-(benzylidene)-3- amino-2-oxazolidone, 8.93 grams of concentrated sulfuric acid, and 30.1 grams (0.124 mol) of 5-nitro-2-furaldehyde diacetate. This mixture is heated to effect the hydrolysis of N-(benzylidene)-3-amino-2-oxazolidone, steam distillation of the benzaldehyde and hydrolysis of 5-nitro-2-furaldehyde diacetate. Approximately 1? hours are required for this reaction to take place. When the bulk of the benzaldehyde has been removed, 50 cc of 99% isopropanol are added, the reaction mixture is refluxed a short time, and the crystals of N(5-nitro-2-furfurylidene)-3-amino-2-oxazolidone are filtered from the hot suspension. The product is washed with water and isopropanol and dried; a yield of 23.3 grams, 92.8% based on N-(benzylidene)-3-amino-2- oxazolidone of MP 254° to 256°C is obtained, according to US Patent 2,759,931.

brand name

Benilen;B-fsudi;Carbopuradin;Dapecfuran;Dectolin;Dialidene;Diarexin;Diarin;Diclofur;Doreplston;Dushel;Enterar;Enteroxon;Framenterol;Ft 15;Furaberin;Furacol l.;Furalatin p.;Furalidan;Furaliqua;Furoxona-cp;Fuvitan;Fuxol;Fuzatyl;Galacid;Gamafur s.;Giarlin;Ginvel;Injecur;Intefuran;Kalpec-f;Lacolysat;Mastisept;Multi-med 2;Multi-med 3;Multi-med 6;Neforox alpha cpto;Neftivit;Nicolen r;Nifulin;Parkestress forte;Saleton;Scantrimon;Sibren;Sirben;Syralbuna;Tetrafur;Tranatogen-ova;Ufa-cfo-400;Uterojekt;Vagifurona;Vetoprim;Vsf-medical g 15.

Therapeutic Function

Topical antiinfective

世界保健機関(WHO)

Furazolidone, a nitrofuran derivative with antibacterial and antiprotozoal activity, was introduced in 1954. In the 1970s it was shown to have a carcinogenic potential following long-term administration to experimental animals. However, the relevance of this to short-term therapy in man has not been established. The risk-benefit assessment varies and furazolidone remains widely available in many countries for the treatment of diarrhoea and enteritis.

抗菌性

It is active against a wide range of enteric pathogens, including Salmonella enterica, Shigella spp., enterotoxigenic Escherichia coli, Campylobacter jejuni, Aeromonas hydrophila, Plesiomonas shigelloides, Vibrio cholerae and V. parahaemolyticus. Yersinia enterocolitica is intrinsically resistant. Furazolidone is also active against the protozoa Giardia lamblia and Trichomonas vaginalis.

獲得抵抗性

Acquired resistance has been observed in V. cholerae O1 and O139, S. enterica serotypes Typhi and Enteritidis, A. hydrophila and Shigella spp. Such resistance may be transferable, and there is cross-resistance with nitrofurantoin. Many of these reports come from the Indian subcontinent, where furazolidone is used widely for treating diarrheal diseases.

一般的な説明

Furazolidone is an effective antiprotozoal and antibacterial agent.

危険性

A questionable carcinogen, use has been restricted.

応用例(製薬)

A non-ionic synthetic compound, available for oral use only. It is poorly soluble in water (40 mg/L) and ethanol (90 mg/L), but dissolves well in dimethylformamide (10 g/L). It decomposes in the presence of alkali.

接触アレルゲン

Furazolidone belongs to the group of nitrofurans. This antimicrobial (antibacterial and antiprotozoal) agent is used in veterinary medicine both topically and orally, particularly in animal feed. Reactions are reported in workers exposed to it in animal feeds. Cross-reactions with other nitrofuran derivatives are rare.

Biochem/physiol Actions

Furazolidone induces interstrand cross-links in subsequent mutation in bacterial cells. It also inhibits mono and diamine oxidase activities in eukaryotes.

薬物動態学

There is substantial absorption (65–70%) after oral administration, but the drug is heavily metabolized, so that only about 5% of the material excreted is microbiologically active. A dose of 5 mg/kg achieves a maximum plasma concentration of around 1 mg/L. Protein binding is about 30%. Intact drug can be found in various body fluids in concentrations approximating to the minimum inhibitory concentration (MIC) for various intestinal pathogens. Less than 1% of the drug is excreted into urine.

臨床応用

Furazolidone is used in gastrointestinal infections and vaginitis. It is mainly used in developing countries to treat diarrheal diseases of varying etiology, but it is not the drug of choice if a specific pathogen has been identified. Use as a secondline agent in giardiasis and as part of multidrug regimens in Helicobacter infection has been advocated.

臨床応用

3-[(5-Nitrofurylidene)amino]-2-oxazolidinone (Furoxone)occurs as a yellow crystalline powder with a bitter aftertaste.It is insoluble in water or alcohol. Furazolidone hasbactericidal activity against a relatively broad range of intestinalpathogens, including S. aureus, E. coli, Salmonella,Shigella, Proteus spp., Enterobacter, and Vibrio cholerae.It is also active against the protozoan Giardia lamblia. It isrecommended for the oral treatment of bacterial or protozoaldiarrhea caused by susceptible organisms. The usualadult dosage is 100 mg 4 times daily.
Only a small fraction of an orally administered dose of furazolidoneis absorbed. Approximately 5% of the oral dose isdetectable in the urine in the form of several metabolites.Some gastrointestinal distress has been reported with its use.Alcohol should be avoided when furazolidone is being usedbecause the drug can inhibit aldehyde dehydrogenase.

副作用

Most reported side effects are mild and only rarely cause discontinuation of treatment. Nausea and vomiting are experienced by around 8% of patients. Other adverse events include neurological reactions (mainly headache; 1.3% of patients), ‘systemic’ reactions such as fever and malaise (0.6%) and skin rashes (0.54%). Administration of furazolidone may give rise to inhibition of monoamine oxidase, and disulfiram-like reactions have been reported.

安全性プロファイル

Poison by ingestion and intraperitoneal routes. Human systemic effects by ingestion: dyspnea, respiratory depression, and eosinophilta. Experimental reproductive effects. Human mutation data reported. Questionable carcinogen. When heated to decomposition it emits toxic fumes of NOx.

Chemical Synthesis

Furazolidone, 3-(5-nitrofurfuryliden)amino-2-oxazolidinone (33.7.8), is synthesized from 2-hydroazinoethanol, which is reacted with diethyloxalate to make 3- amino-2-oxazolidone. Reacting this with benzaldehyde gives the corresponding hydrazone (33.3.7). Purifying the resulting product and then reacting it with 5-nitrofurfurol gives furazolidone.

Veterinary Drugs and Treatments

Furazolidone is usually a drug of second choice in small animals to treat enteric infections caused by the organisms listed below. Because it is no longer commercially available (in the USA), it may be difficult to locate.

フラゾリドン 上流と下流の製品情報

原材料

準備製品


フラゾリドン 生産企業

Global( 338)Suppliers
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67-45-8(フラゾリドン)キーワード:


  • 67-45-8
  • 2-Furanmethanimine, 5-nitro-N-(2-oxo-3-oxazolidinyl)-
  • 2-Oxazolidinone, 3-((5-nitrofurfurylidene)amino)-
  • 2-Oxazolidinone, 3-((5-nitrofurfurylidine)amino)-
  • 2-Oxazolidinone, 3-[[(5-nitro-2-furanyl)methylene]amino]-
  • 2-Oxazolidinone,3-[[(5-nitro-2-furanyl)methylene]amino]-
  • 3-(((5-nitro-2-furanyl)methylene)amino)-2-oxazolidinon
  • 3-(((5-Nitro-2-furanyl)methylene)amino)-2-oxazolidinone
  • Furaxon
  • Furaxone
  • Furazol
  • Furazolidine
  • Furazolidon
  • furazolidone(notsubjectto
  • Furazolidone in stock GMP Factory
  • furazolidone(notsubjecttofifra:8709-e
  • furazolidone(notsubjecttofifra:8709-epm24)
  • Furazon
  • Furidon
  • Furovag
  • Furox
  • Furoxal
  • Furoxane
  • Furoxon
  • Furoxone
  • Furoxone Swine Mix
  • furoxoneswinemix
  • Furozolidine
  • Giardil
  • Giarlam
  • Medaron
  • ネフチン
  • フロキソン
  • 3-(5-ニトロフルフリリデンアミノ)-4,5-ジヒドロオキサゾール-2(3H)-オン
  • 3-(5-ニトロフルフリリデンアミノ)-2-オキサゾリジノン
  • フロキサン
  • 3-[[(5-ニトロフラン-2-イル)メチレン]アミノ]オキサゾリジン-2-オン
  • ニフリドン
  • フラゾリドン標準品
  • 3-[(5-ニトロフルフリリデン)アミノ]-2-オキサゾリジノン
  • フラゾリドン
  • 抗トリコモナス薬
  • 抗微生物薬
  • 抗原虫薬
  • 尿路防腐薬
  • 駆虫薬
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