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푸라졸리돈

푸라졸리돈
푸라졸리돈 구조식 이미지
카스 번호:
67-45-8
한글명:
푸라졸리돈
동의어(한글):
푸라졸리돈;퓨라졸리돈
상품명:
Furazolidone
동의어(영문):
Furox;Neftin;NF 180;nf-180;Furall;Furaxon;Furazol;Furazon;Furidon;Furovag
CBNumber:
CB8452405
분자식:
C8H7N3O5
포뮬러 무게:
225.16
MOL 파일:
67-45-8.mol

푸라졸리돈 속성

녹는점
254-256°C (dec.)
끓는 점
366.66°C (rough estimate)
밀도
1.5406 (rough estimate)
굴절률
1.7180 (estimate)
인화점
2 °C
저장 조건
Keep in dark place,Sealed in dry,Room Temperature
용해도
formic acid: soluble50mg/mL
산도 계수 (pKa)
-1.98±0.20(Predicted)
물리적 상태
powder
색상
yellow
최대 파장(λmax)
365nm(DMSO)(lit.)
감도
Light Sensitive
Merck
14,4300
BRN
8317414
안정성
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
PLHJDBGFXBMTGZ-UITAMQMPSA-N
IARC
3 (Vol. 31, Sup 7) 1987
NIST
Furazolidone(67-45-8)
EPA
Furazolidone (67-45-8)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,F
위험 카페고리 넘버 62-40-36-20/21/22-11-68
안전지침서 36-22-36/37-16
WGK 독일 3
RTECS 번호 RQ3675000
TSCA Yes
HS 번호 29349990
유해 물질 데이터 67-45-8(Hazardous Substances Data)
기존화학 물질 KE-25992
그림문자(GHS):
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H303 삼키면 유해할 수 있음 급성 독성 물질 - 경구 구분 5 P312
H341 유전적인 결함을 일으킬 것으로 의심됨 (노출되어도 생식세포 유전독성을 일으키지 않는다는 결정적인 증거가 있는 노출경로가 있다면 노출경로 기재) 생식세포 변이원성 물질 구분 2 경고 P201,P202, P281, P308+P313, P405,P501
H361 태아 또는 생식능력에 손상을 일으킬 것으로 의심됨 생식독성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
예방조치문구:
P201 사용 전 취급 설명서를 확보하시오.
P202 모든 안전 조치 문구를 읽고 이해하기 전에는 취급하지 마시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P281 요구되는 개인 보호구를 착용하시오
P308+P313 노출 또는 접촉이 우려되면 의학적인 조치· 조언를 구하시오.
P405 밀봉하여 저장하시오.

푸라졸리돈 C화학적 특성, 용도, 생산

개요

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.

화학적 성질

solid

Originator

Tricofuron,Norwich Eaton,US,1955

용도

Antimicrobial.

용도

Antiprotozoal; antibacterial

정의

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.

상표명

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

World Health Organization (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.

Antimicrobial activity

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.

원료

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.

위험도

A questionable carcinogen, use has been restricted.

Pharmaceutical Applications

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.

색상 색인 번호

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.

Pharmacokinetics

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.

Clinical Use

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.

Clinical Use

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.

부작용

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.

Safety Profile

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.

푸라졸리돈 준비 용품 및 원자재

원자재

준비 용품


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