플루시토신

플루시토신
플루시토신 구조식 이미지
카스 번호:
2022-85-7
한글명:
플루시토신
동의어(한글):
플루시토신;플루시토신(FLUCYTOSINE)
상품명:
Fluorocytosine
동의어(영문):
5-FLUOROCYTOSINE;FLUCYTOSINE;5-FC;ancobon;FLUCYTOSIN;5-FLUCYTOSINE;5-Flurocytosine;4-amino-5-fluoropyrimidin-2(1H)-one;Flurocytosine;5-fluorocytosin
CBNumber:
CB6744939
분자식:
C4H4FN3O
포뮬러 무게:
129.09
MOL 파일:
2022-85-7.mol
MSDS 파일:
SDS

플루시토신 속성

녹는점
298-300 °C (dec.) (lit.)
밀도
1.3990 (estimate)
증기압
0Pa at 25℃
저장 조건
2-8°C
용해도
물에 조금 녹고, 에탄올에 약간 녹습니다(96%).
물리적 상태
결정성 분말
산도 계수 (pKa)
3.26(at 25℃)
색상
흰색에서 거의 흰색
수용성
1.5g/100mL(25℃)
감도
Light Sensitive
Merck
14,4125
BRN
127285
BCS Class
1
안정성
감광성
InChIKey
XRECTZIEBJDKEO-UHFFFAOYSA-N
LogP
-1.36 at 22.1℃ and pH6.4-6.9
해리상수
2.74-10.71 at 21.4℃
CAS 데이터베이스
2022-85-7(CAS DataBase Reference)
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
위험품 표기 Xn,T,Xi
위험 카페고리 넘버 40-36/37/38-63
안전지침서 22-24/25-45-36/37-36/37/39-27-26
WGK 독일 2
RTECS 번호 HA6040000
F 고인화성물질 10-23
위험 참고 사항 Toxic/Light Sensitive
위험 등급 IRRITANT, LIGHT SENSITIVE
HS 번호 29335990
유해 물질 데이터 2022-85-7(Hazardous Substances Data)
독성 LD50 in mice (mg/kg): >2000 orally and s.c.; 1190 i.p.; 500 i.v. (Grunberg, 1963)
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H361 태아 또는 생식능력에 손상을 일으킬 것으로 의심됨 생식독성 물질 구분 2 경고 P201, P202, P281, P308+P313, P405,P501
예방조치문구:
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
NFPA 704
1
0 0

플루시토신 MSDS


2-Hydroxy-4-amino-5-fluoropyrimidine

플루시토신 C화학적 특성, 용도, 생산

개요

5-Fluorocytosine (5-FC), a fluorinated pyrimidine analog, is a synthetic antimycotic prodrug that is converted by cytosine deaminase to 5-fluorouracil. 5-Fluorouracil, a widely used cytotoxic drug, is further metabolized to fluorinated ribo- and deoxyribonucleotides, resulting in the inhibition of DNA and protein synthesis, which has multiple effects including inhibition of Candida species and C. neoformans infections and cytotoxicity towards cancer cells. In combination with a retroviral replicating vector carrying a cytosine deaminase prodrug-activating gene, 5-FC has been shown to selectively eliminate CT26 and Tu-2449 tumor cells in vitro (IC50s = 4.2 and 1.5 μM, respectively) and to significantly improve survival and reduce tumor size (at a dose of 500 mg/kg) in two different syngeneic mouse glioma models.

화학적 성질

White Crystalline Solid

용도

5-Fluorocytosine acts as an antidiabetic, antifungal and antimicrobial agent. It is useful for the treatment of serious infections arises due to susceptible strains of Candida or Cryptococcus neoformans and chromomycosis. Further, it is employed in studies on TMP biosynthesis.

Indications

Flucytosine (Ancobon) is a synthetic, fluorinated pyrimidine that is structurally related to fluorouracil (FU) and floxuridine. It can be fungistatic and fungicidal. Although it is used more frequently in the treatment of systemic infections caused by Candida and Cryptococcus, dermatologic indications may include infections due to chromomycosis, sporotrichosis, Cladosporium, and Sporothrix species. It is generally ineffective against Aspergillus species.

정의

ChEBI: Flucytosine is an organofluorine compound that is cytosine that is substituted at position 5 by a fluorine. A prodrug for the antifungal 5-fluorouracil, it is used for the treatment of systemic fungal infections. It has a role as a prodrug. It is an organofluorine compound, a pyrimidone, an aminopyrimidine, a nucleoside analogue and a pyrimidine antifungal drug. It is functionally related to a cytosine.

Antimicrobial activity

The spectrum of activity is restricted to Candida spp., Cryptococcus spp. and some fungi causing chromoblastomycosis.

원료

About 2–3 of Candida spp. isolates (more in some centers) are resistant before treatment starts, and resistance may develop during treatment. The most common cause of resistance appears to be loss of the enzyme uridine monophosphate pyrophosphorylase.

Pharmaceutical Applications

A synthetic fluorinated pyrimidine available for intravenous infusion or oral administration.

Mechanism of action

Flucytosine (5-flucytosine, 5-FC; Ancoban) is a fluorinated pyrimidine analogue of cytosine that was originally synthesized for possible use as an antineoplastic agent. It is indicated only for the treatment of serious systemic infections caused by susceptible strains of Candida and Cryptococcus spp.The mechanism of action of 5-fluorocytosine (5-FC)has been studied in detail.The drug enters the fungal cell by active transport onATPases that normally transport pyrimidines. Once insidethe cell, 5-fluorocytosine is deaminated in a reaction catalyzedby cytosine deaminase to yield 5-fluorouracil(5-FU). 5-Fluorouracil is the active metabolite of the drug.5-Fluorouracil enters into pathways of both ribonucleotideand deoxyribonucleotide synthesis. The fluororibonucleotidetriphosphates are incorporated into RNA, causingfaulty RNA synthesis. This pathway causes cell death. Inthe deoxyribonucleotide series, 5-fluorodeoxyuridinemonophosphate (F-dUMP) binds to 5,10-methylenetetrahydrofolicacid, interrupting the one-carbon pool substratethat feeds thymidylate synthesis. Hence, DNA synthesisis blocked.

Pharmacology

5-FC is well absorbed orally, with greater than 90% bioavailability. The serum half-life is 3 to 5 hours, with serum levels peaking 4 to 6 hours after a single dose.The drug is widely distributed in body fluids, with cerebrospinal fluid levels 60 to 80% of serum levels.The drug also penetrates well into urine, aqueous humor, and bronchial secretions.Minimal serum protein binding allows more than 90% of each dose to be excreted in the urine; significant dosage reductions are required in the presence of renal impairment. 5-FC can be removed by both hemodialysis and peritoneal dialysis. 5-FC conversion to toxic metabolites may occur in mammalian cells to a limited extent, which accounts for 5-FC toxicity.

Pharmacokinetics

Oral absorption: Complete
Cmax 25 mg/kg 6-hourly oral: 70–80 mg/L after 1–2 h
Plasma half-life: 3–6 h
Volume of distribution: 0.7–1 L/kg
Plasma protein binding c. 12%
Absorption is slower in persons with impaired renal function, but peak concentrations are higher. Levels in the CSF are around 75% of the simultaneous serum concentration. More than 90% of a dose of flucytosine is excreted in the urine in unchanged form. The serum half-life is much longer in renal failure, necessitating modification of the dosage regimen: for patients with a creatinine clearance below 40 mL/ min the dosage interval should be doubled to 12 h; in severe renal failure the dosage interval should be further increased to once daily or less, based on frequent serum drug concentration measurements.

부작용

Nausea, vomiting, abdominal pain and diarrhea are common. Serious side effects include myelosuppression and hepatic toxicity; they occur more frequently when serum concentrations exceed 100 mg/L.
The nephrotoxic effects of amphotericin B can result in elevated blood concentrations of flucytosine, and levels of the latter drug should be monitored when these compounds are administered together. When 5-FC is prescribed alone to patients with normal renal function, skin rash, epigastric distress, diarrhea, and liver enzyme elevations can occur.

신진 대사

Flucytosine itself is not cytotoxic but, rather, is a pro-drug that is taken up by fungi and metabolized to 5-fluorouracil (5-FU) by fungal cytidine deaminase. Then, 5-FU is converted to 5-fluorodeoxyuridine, which as a thymidylate synthase inhibitor interferes with both protein and RNA biosynthesis. 5-Fluorouracil is cytotoxic and is employed in cancer chemotherapy. Human cells do not contain cytosine deaminase and, therefore, do not convert flucytosine to 5-FU. Some intestinal flora, however, do convert the drug to 5-FU, so human toxicity does result from this metabolism.

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