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Flucytosin Produkt Beschreibung

Fluorocytosine Struktur
2022-85-7
CAS-Nr.
2022-85-7
Bezeichnung:
Flucytosin
Englisch Name:
Fluorocytosine
Synonyma:
5-FC;ancobon;ancotil;ALCOBON;ro2-9915;FLUCYSTINE;FLUCYTOSIN;FLUCYTOSINE;fluocytosine;Flurocytosine
CBNumber:
CB6744939
Summenformel:
C4H4FN3O
Molgewicht:
129.09
MOL-Datei:
2022-85-7.mol

Flucytosin Eigenschaften

Schmelzpunkt:
298-300 °C (dec.)(lit.)
Dichte
1.3990 (estimate)
storage temp. 
2-8°C
Löslichkeit
Sparingly soluble in water, slightly soluble in ethanol (96 per cent)
Aggregatzustand
Crystalline Powder
pka
3.26(at 25℃)
Farbe
White to almost white
Wasserlöslichkeit
1.5g/100mL (25 ºC)
Sensitive 
Light Sensitive
Merck 
14,4125
BRN 
127285
Stabilität:
Light Sensitive
InChIKey
XRECTZIEBJDKEO-UHFFFAOYSA-N
CAS Datenbank
2022-85-7(CAS DataBase Reference)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,T,Xi
R-Sätze: 40-36/37/38-63
S-Sätze: 22-24/25-45-36/37-36/37/39-27-26
WGK Germany  2
RTECS-Nr. HA6040000
10-23
Hazard Note  Toxic/Light Sensitive
HazardClass  IRRITANT, LIGHT SENSITIVE
HS Code  29335990
Giftige Stoffe Daten 2022-85-7(Hazardous Substances Data)
Toxizität LD50 in mice (mg/kg): >2000 orally and s.c.; 1190 i.p.; 500 i.v. (Grunberg, 1963)
Bildanzeige (GHS)
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenität Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P281 Vorgeschriebene persönliche Schutzausrüstung verwenden.
P308+P313 BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.
P405 Unter Verschluss aufbewahren.

Flucytosin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R40:Verdacht auf krebserzeugende Wirkung.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-Sätze Betriebsanweisung:

S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S27:Beschmutzte, getränkte Kleidung sofort ausziehen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

Chemische Eigenschaften

White Crystalline Solid

Verwenden

antidiabetic

Verwenden

antifungal and antimicrobial agent

Verwenden

5-FC is a toxic antifungal/antimicrobial agent

Definition

ChEBI: 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.

Trademarks

Ancobon (Valeant).

Antimicrobial activity

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

Acquired resistance

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.

Pharmazeutische Anwendungen

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. 5-FC is converted to 5-fluorouracil inside the cell by the fungal enzyme cytosine deaminase. Subsequently, 5-FC metabolites interfere with fungal DNA synthesis by inhibiting thymidylate synthetase. Incorporation of these metabolites into fungal RNA may inhibit protein synthesis.

Pharmakokinetik

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.

Pharmakologie

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.

Clinical Use

Candidosis (in combination with amphotericin B or fluconazole)
Cryptococcosis (in combination with amphotericin B or fluconazole)
Monitoring of flucytosine concentrations is desirable in all patients, and mandatory in those with renal impairment.

Clinical Use

5-Fluorocytosine, 5-FC, 4-amino-5-fluoro-2(1H)-pyrimidinone, 2-hydroxy-4-amino-5-fluoropyrimidine (Ancobon). 5-Fluorocytosine is an orally active antifungal agent with a very narrow spectrum of activity. 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.

Clinical Use

Flucytosine has significant antifungal activity against C. albicans, other Candida spp., C. neoformans, and the fungal organisms responsible for chromomycosis. Not considered the drug of choice for these fungal infections, 5-FC does remain useful as part of combination therapy for systemic candidiasis and cryptococcal meningitis and as an alternative drug for chromomycosis. When it is used as monotherapy, resistance and clinical failure are common. Potential mechanisms for drug resistance include decreased fungal cell membrane permeability and reduced levels of fungal cytosine deaminase. Combination therapy with amphotericin B and flucytosine in the treatment of cryptococcal meningitis and deep-seated Candida infections, such as septic arthritis and meningitis, permits reduced dosing of amphotericin B and prevents the emergence of 5-FC resistance. When higher doses of amphotericin B are used, combination therapy with 5-FC confers no additional clinical benefit except in the treatment of Candida endophthalmitis, where tissue penetration remains problematic.

Nebenwirkungen

When 5-FC is prescribed alone to patients with normal renal function, skin rash, epigastric distress, diarrhea, and liver enzyme elevations can occur.When it is prescribed to patients with renal insufficiency or to patients receiving concurrent amphotericin B therapy, blood levels of 5-FC may rise, and bone marrow toxicity leading to leukopenia and thrombocytopenia is common. 5-FC serum levels should be closely monitored in patients with renal insufficiency. Because of baseline leukopenia, 5-FC is often not tolerated by end-stage HIVinfected patients with disseminated fungal infection.

Nebenwirkungen

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.

Flucytosin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Flucytosin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 485)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
China Synchem Technology Co.,Ltd.
0552-4929304
0552-4928800 sales@cnsynchem.com CHINA 45 55
Anhui Royal Chemical Co., Ltd.
+86-025-86736275
dana.jiang@royal-chem.com CHINA 488 55
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3194 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21676 58
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 493 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20672 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32447 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile; WhatsApp; Telegram)
+86-571-56059825 fandachem@gmail.com CHINA 2887 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 661 60

2022-85-7(Flucytosin)Verwandte Suche:


  • 恩曲他滨杂质Ⅰ(5-氟胞嘧啶)
  • 4-amino-5-fluoro-2(1h)-pyrimidinon
  • 4-Amino-5-fluoro-2(1H)-pyrmidinone
  • 5-fluorocystosine
  • 5-fluorocytosin
  • 5-fluoro-cytosin
  • fluocytosine
  • 4-Amino-5-Fluoro-2(1H)-pyrimidine, Flucytosine, 5-FC
  • 5-Fluorocytosine98%
  • 5-FLUOROCYTOSINE(FLUCYTOSINE)
  • FLUCYTOSINE (5-FLUOROCYTOSINE)
  • 5-FLUOROCYTOSINE USP/BP
  • 6-Amino-5-fluoro-1H-pyrimidin-2-one
  • 5-FLUOROCYTOSINE extrapure
  • Flurocytosine
  • 4-amino-5-fluoro-2(1H)-pyrimidinone, Flucytosine
  • 2(1H)-Pyrimidinone, 6-amino-5-fluoro-
  • 5-Fluorocytosine,4-amino-5-fluoro-2(1H)-pyrimidinone, Flucytosine
  • Flucytosine (200 mg)G0E1511.000mg/mg(dr)
  • 5-FC,RO 2-9915
  • 4-Amino-5-fluoropyrimidin-2(1H)-one, 4-Amino-1,2-dihydro-5-fluoro-2-oxopyrimidine
  • ro2-9915
  • TIMTEC-BB SBB000061
  • FLUCYSTINE
  • FLUCYTOSIN
  • FLUCYTOSINE
  • fluorocytosine
  • 2-hydroxy-4-amino-5-fluoropyrimidine
  • 5-FLUOROCYTOSINE
  • 5-FLUCYTOSINE
  • 5-FC
  • ancobon
  • ancotil
  • ALCOBON
  • 4-AMINO-5-FLUORO-2(1H)-PYRIMIDINE
  • 4-amino-5-fluoro-2(1h)-pyrimidinone
  • 4-AMINO-5-FLUORO-2-HYDROXYPYRIMIDINE
  • 4-AMINO-5-FLUORO-3H-PYRIMIDIN-2-ONE
  • 5-Flurocytosine
  • 4-amino-5-fluoropyrimidin-2(1H)-one
  • 5-FLUOR-CYTOSIN
  • 5-FLUROCYTOSINE/FLUCYTOSINE
  • FlucytosineTablets
  • 2(1H)-Pyrimidinone, 4-amino-5-fluoro- (9CI)
  • 4-Amino-5-fluoro-2[1H]-pyrimidone
  • 5-Fluorocytosine, 99+%
  • Flucytosine (200 mg)
  • 4-aMino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)oxolan-2-yl]-5-fluoro-1,2-dihydropyriMidin-2-one
  • NSC 103805 6-AMino-5-fluoro-
  • 4-Amino-5-fluoro-2-hydroxypyrimidine Flucytosine
  • 6-AMino-2-oxo-5-fluoropyriMidine
  • 5-Fluorocytosine USP/EP
  • 5 - fluorine cytosine
  • 6-amino-5-fluoro-2(1H)-pyrimidinone
  • Flucytosine for system suitability
  • 5-Fluorocytosine Vetec(TM) reagent grade, 99%
  • 4-amino-5-fluoropyrimidin-2-ol
  • 4-Amino-5-fluoro-2-hydroxypyrimidine 4-amino-5-fluoro-2(1H)-pyrimidinone Flucytosine
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