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나이트로푸란토인

나이트로푸란토인
나이트로푸란토인 구조식 이미지
카스 번호:
67-20-9
한글명:
나이트로푸란토인
동의어(한글):
니트로푸란토인;나이트로푸란토인;나이트로퓨란계화합물;나이트로퓨란토인
상품명:
Nitrofurantoin
동의어(영문):
Upiol;Furina;Ituran;Macpac;Nitoin;Nitrex;N-Toin;Urodin;Cystit;Furalan
CBNumber:
CB7346080
분자식:
C8H6N4O5
포뮬러 무게:
238.16
MOL 파일:
67-20-9.mol

나이트로푸란토인 속성

녹는점
268°C
끓는 점
380.75°C (rough estimate)
밀도
1.5824 (rough estimate)
굴절률
1.6700 (estimate)
저장 조건
0-6°C
용해도
DMF: soluble50mg/mL
산도 계수 (pKa)
7.2(at 25℃)
물리적 상태
crystalline
색상
yellow
수용성
<0.01 g/100 mL at 19 ºC
감도
Light Sensitive & Hygroscopic
최대 파장(λmax)
358nm(MeOH)(lit.)
Merck
14,6599
BRN
893207
안정성
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 데이터베이스
67-20-9(CAS DataBase Reference)
NIST
Hydantoin, n-(5-nitro-2-furfurylidene)-1-amino-(67-20-9)
EPA
2,4-Imidazolidinedione, 1-[[(5-nitro-2-furanyl)methylene] amino]-(67-20-9)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn
위험 카페고리 넘버 22-42/43
안전지침서 22-36/37-45
유엔번호(UN No.) 2811
WGK 독일 3
RTECS 번호 MU2800000
TSCA Yes
위험 등급 6.1(b)
포장분류 III
HS 번호 29349990
유해 물질 데이터 67-20-9(Hazardous Substances Data)
그림문자(GHS):
신호 어: Danger
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 P264, P270, P301+P312, P330, P501
H317 알레르기성 피부 반응을 일으킬 수 있음 피부 과민성 물질 구분 1 경고 P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H334 흡입 시 알레르기성 반응, 천식 또는 호흡 곤란 등을 일으킬 수 있음 호흡기 과민성 물질 구분 1 위험 P261, P285, P304+P341, P342+P311,P501
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P284 호흡 보호구를 착용하시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P342+P311 호흡기 증상이 나타나면 의료기관(의사)의 진찰을 받으시오.

나이트로푸란토인 MSDS


Nitrofurantoin

나이트로푸란토인 C화학적 특성, 용도, 생산

화학적 성질

lemon yellow crystalline powder

용도

counterirritant

용도

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.

정의

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.

상표명

Ivadantin (Procter & Gamble);Furan;Nitrofan.

Antimicrobial activity

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.

원료

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.

일반 설명

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

공기와 물의 반응

Insoluble in water.

반응 프로필

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.

위험도

Questionable carcinogen.

화재위험

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

Pharmaceutical Applications

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.

Pharmacokinetics

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.

Clinical Use

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

부작용

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.

Safety Profile

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.

나이트로푸란토인 준비 용품 및 원자재

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