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Fluoruracil Produkt Beschreibung

5-Fluorouracil Struktur
51-21-8
CAS-Nr.
51-21-8
Bezeichnung:
Fluoruracil
Englisch Name:
5-Fluorouracil
Synonyma:
FU;5-FL;Ulup;5-FU;Fluri;Arumel;Efudex;Efudix;Efurix;U-8953
CBNumber:
CB8162744
Summenformel:
C4H3FN2O2
Molgewicht:
130.08
MOL-Datei:
51-21-8.mol

Fluoruracil Eigenschaften

Schmelzpunkt:
282-286 °C (dec.)(lit.)
Siedepunkt:
190-200°C/0.1mmHg
Dichte
1.4593 (estimate)
storage temp. 
Store at 0-5
Löslichkeit
H2O: 10 mg/mL, clear
pka
pKa 8.0±0.1 (H2O) (Uncertain);3.0±0.1(H2O) (Uncertain)
Aggregatzustand
powder
Farbe
white
PH
4.3-5.3 (10g/l, H2O, 20℃)
Wasserlöslichkeit
12.2 g/L 20 ºC
Sensitive 
Air Sensitive
Merck 
14,4181
BRN 
127172
Stabilität:
Stable. Light sensitive. Combustible. Incompatible with strong oxidizing agents, strong bases.
InChIKey
GHASVSINZRGABV-UHFFFAOYSA-N
CAS Datenbank
51-21-8(CAS DataBase Reference)
NIST chemische Informationen
2,4-Pyrimidinedione, 5-fluoro-(51-21-8)
EPA chemische Informationen
5-Fluorouracil (51-21-8)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,T,C,Xi
R-Sätze: 22-20/21/22-52-25
S-Sätze: 36-36/37-36/37/39-22-45-26
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS-Nr. YR0350000
10-23
Hazard Note  Irritant/Highly Toxic
TSCA  T
HazardClass  6.1
PackingGroup  III
HS Code  29335995
Giftige Stoffe Daten 51-21-8(Hazardous Substances Data)
Toxizität LD50 orally in Rabbit: 230 mg/kg
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H302 Gesundheitsschädlich bei Verschlucken. Akute Toxizität oral Kategorie 4 Warnung P264, P270, P301+P312, P330, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenität Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
H351 Kann vermutlich Krebs verursachen. Karzinogenität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H360 Kann die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Fertility (Fruchtbarkeit) Kategorie 1 Achtung
H373 Kann die Organe schädigen bei längerer oder wiederholter Exposition. Spezifische Zielorgan-Toxizität (wiederholte Exposition) Kategorie 2 Warnung P260, P314, P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

Fluoruracil Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.

S-Sätze Betriebsanweisung:

S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S22:Staub nicht einatmen.

Chemische Eigenschaften

White or almost white, crystalline powder

Chemische Eigenschaften

Fluorouracil is a white crystalline solid. Practically odorless.

Verwenden

antineoplastic, pyrimidine antimetabolite

Verwenden

5-Fluoro Uracil is an active metabolite of Doxifluridine (D556750).

Verwenden

A potent antineoplastic agent in clinical use. Also an inhibitor of DNA synthesis

Indications

Fluorouracil (5-fluorouracil, 5-fluorouracil, Efudex, Adrucil) is a halogenated pyrimidine analogue that must be activated metabolically. The active metabolite that inhibits DNA synthesis is the deoxyribonucleotide 5-fluoro-2'deoxyuridine-S'-phosphate (FdUMP). 5- Fluorouracil is selectively toxic to proliferating rather than non-proliferating cells and is active in both the G1- and S-phases. The target enzyme inhibited by 5-fluorouracilfluorouracil is thymidylate synthetase.
methylenetetrahydrofolate dihydrofolate The carbon-donating cofactor for this reaction is N5,N10 methylenetetrahydrofolate, which is converted to dihydrofolate. The reduced folate cofactor occupies an allosteric site on thymidylate synthetase, which allows for the covalent binding of 5-FdUMP to the active site of the enzyme.

Trademarks

Adrucil (Pharmacia & Upjohn); Adrucil (Sicor); Carac (Sanofi Aventis); Efudex (Valeant); Fluoroplex (Allergan).

Allgemeine Beschreibung

White to nearly white crystalline powder; practically odorless. Used as an anti neoplastic drug, chemosterilant for insects.

Allgemeine Beschreibung

The drug is available in a 500-mg or 10-mL vial for IV useand as a 1% and 5% topical cream. 5-FU is used in the treatmentof several carcinoma types including breast cancer,colorectal cancer, stomach cancer, pancreatic cancer, andtopical use in basal cell cancer of the skin. The mechanism ofaction includes inhibition of the enzyme TS by the deoxyribosemonophosphate metabolite, 5-FdUMP. The triphosphatemetabolite is incorporated into DNA and the ribosetriphosphate into RNA. These incorporations into growingchains result in inhibition of synthesis and function of DNAand RNA. Resistance can occur as a result of increased expressionof TS, decreased levels of reduced folate substrate5,10-methylenetetrahydrofolate, or increased levels of dihydropyrimidinedehydrogenase. Dihydropyrimidine dehydrogenaseis the main enzyme responsible for 5-FU catabolism.
Bioavailability following oral absorption is erratic.Administration of 5-FU by IV yields high drug concentrationsin bone marrow and liver. The drug does distribute intothe central nervous system (CNS). Significant drug interactionsinclude enhanced toxicity and antitumor activity of5-FU following pretreatment with leucovorin. Toxicities includedose-limiting myelosuppression, mucositis, diarrhea,and hand–foot syndrome (numbness, pain, erythema, dryness,rash, swelling, increased pigmentation, nail changes,pruritus of the hands and feet).

Air & Water Reaktionen

Insoluble in water.

Reaktivität anzeigen

5-Fluorouracil may be sensitive to prolonged exposure to light. Solutions discolor on storage. 5-Fluorouracil can react with oxidizing agents and strong bases. Incompatible with methotrexate sodium.

Hazard

Questionable carcinogen.

Health Hazard

Minimum toxic dose in humans is approximately 450 mg/kg (total dose) over 30 days for the ingested drug. Intravenous minimum toxic dose in humans is a total dose of 6 mg/kg over three days. Depression of white blood cells occurred after intravenous administrative of a total dose of 480 mg/kg over 32 days. Occasional neuropathy and cardiac toxicity have been reported. Do not use during pregnancy. Patients with impaired hepatic or renal function, with a history of high-dose pelvic irradiation or previous use of alkylating agents should be treated with extreme caution. Patients with nutritional deficiencies and protein depletion have a reduced tolerance to 5-Fluorouracil.

Brandgefahr

Emits very toxic fumes of flourides and nitrogen oxides when heated to decomposition. Avoid decomposing heat.

Biologische Aktivität

Anticancer agent. Metabolized to form fluorodeoxyuridine monophosphate (FdUMP), fluorodeoxyuridine triphosphate (FdUTP) and fluorouridine (FUTP). FdUMP inhibits thymidylate reductase causing a reduction in dTMP synthesis. FUTP and FdUTP are misincorporated into RNA and DNA respectively.

Mechanism of action

5-Fluorouracil (FU) is converted intracellularly to several active metabolites: fluorodeoxyuridine monophosphate (FdUMP), fluorodeoxyuridine triphosphate (FdUTP), and fluorouridine triphosphate (FUTP). The active metabolites of 5-FU disrupt RNA synthesis (FUTP), inhibit the action of thymidylate synthase (TS)—a nucleotide synthetic enzyme (FdUMP)—and can also be directly misincorporated into DNA (FdUTP). The rate-limiting enzyme in 5-FU catabolism is dihydropyrimidine dehydrogenase (DPD), which converts 5-FU to dihydrofluorouracil (DHFU). Over 80% of administered 5-FU is normally catabolized primarily in the liver, where DPD is abundantly expressed.

5-Fluorouracil (5-FU) is converted to three major active metabolites: (1) fluorodeoxyuridine monophosphate (FdUMP), (2) fluorodeoxyuridine triphosphate (FdUTP), and (3) fluorouridine triphosphate (FUTP). The main mechanism of 5-FU activation is conversion to fluorouridine monophosphate (FUMP) either directly by orotate phosphoribosyl transferase (OPRT), or indirectly via fluorouridine (FUR) through the sequential action of uridine phosphorylase (UP) and uridine kinase (UK). FUMP is then phosporylated to fluorouridine diphosphate (FUDP), which can be either further phosphorylated to the active metabolite fluorouridine triphosphate (FUTP), or converted to fluorodeoxyuridine diphosphate (FdUDP) by ribonucleotide reductase (RR). In turn, FdUDP can either be phosphorylated or dephosphorylated to generate the active metabolites FdUTP and FdUMP respectively. An alternative activation pathway involves the thymidine phosphorylase catalyzed conversion of 5-FU to fluorodeoxyuridine (FUDR), which is then phosphorylated by thymidine kinase (TK) to the thymidylate synthase (TS) inhibitor, FdUMP. Dihydropyrimidine dehydrogenase (DPD)-mediated conversion of 5-FU to dihydrofluorouracil (DHFU) is the rate-limiting step of 5-FU catabolism in normal and tumor cells.

Mechanism of action

Another action proposed for 5-fluorouracil may involve the incorporation of the nucleotide 5-fluorouridine triphosphate (5-FUTP) into RNA. The cytotoxic role of these “fraudulent” 5-fluorouracil-containing RNAs is not well understood.
Several possible mechanisms of resistance to 5-fluorouracil have been identified, including increased synthesis of the target enzyme, altered affinity of thymidylate synthetase for FdUMP, depletion of enzymes (especially uridine kinase) that activate 5-fluorouracil to nucleotides, an increase in the pool of the normal metabolite deoxyuridylic acid (dUMP), and an increase in the rate of catabolism of 5-fluorouracil.
The drug has been administered orally, but absorption by this route is erratic. The plasma half-life of 5- fluorouracil after intravenous injection is 10 to 20 minutes. It readily enters CSF. Less than 20% of the parent compound is excreted into the urine, the rest being largely metabolized in the liver.

Pharmakologie

Local inflammatory reactions characterized by erythema, edema, crusting, burning, and pain are common (and, some would argue, desirable) but may be minimized by reduced frequency of application or use in combination with a topical corticosteroid.

Clinical Use

5-Fluorouracil (Efudex, Fluoroplex) is an antimetabolite used for the topical treatment of actinic keratoses. It is also useful for the treatment of superficial basal cell carcinomas when conventional surgical modalities are impractical.

Clinical Use

5-Fluorouracil (FU) is widely used in the treatment of a range of cancers including breast and cancers of the aerodigestive tract, but has had the greatest impact in colorectal cancer. 5-FU-based chemotherapy improves overall and disease-free survival of patients with resected stage III colorectal cancer. Nonetheless, response rates for 5-FU-based chemotherapy as a first-line treatment for advanced colorectal cancer are only between 10 and 15%. Combination of 5-FU with newer chemotherapies, such as irinotecan and oxaliplatin, has improved the response rates for advanced colorectal cancer to between 40 and 50%.

Clinical Use

5-Fluorouracil is used in several combination regimens in the treatment of breast cancer. It also has palliative activity in gastrointestinal adenocarcinomas, including those originating in the stomach, pancreas, liver, colon, and rectum. Other tumors in which some antitumor effects have been reported include carcinomas of the ovary, cervix, oropharynx, bladder, and prostate. Topical 5-fluorouracil cream has been useful in the treatment of premalignant keratoses of the skin and superficial basal cell carcinomas, but it should not be used in invasive skin cancer.

Nebenwirkungen

Patients who are genetically deficient in this enzyme will experience a more pronounced effect from this drug and are at significant risk for use-limiting toxicity. In general, women clear fluorouracil faster than men do. Dosage adjustments usually are not required in hepatic or renal dysfunction. Major toxicities are related to bone marrow depression, stomatitis/esophagopharyngitis, and potential GI ulceration. Nausea and vomiting are common. Solutions of fluorouracil are light sensitive, but discolored products that have been properly stored and protected from light are still safe to use.

Sicherheitsprofil

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by parented and rectal routes. Experimental teratogenic and reproductive effects. Human systemic effects: EKG changes, bone marrow changes, cardiac, pulmonary, and gastrointestinal effects. Human mutation data reported. A human skin irritant. Questionable carcinogen. When heated to decomposition it emits very toxic fumes of Fand NOx.

mögliche Exposition

This material is used as an antineo plastic drug for cancer treatment and as a chemosterilant for insects.

Veterinary Drugs and Treatments

5-fluorouracil is a potent cytotoxic chemotherapeutic agent used for the topical therapy of equine limbal and eyelid squamous cell carcinoma. It is also used as an antimetabolite to limit fibrosis over the body of gonioimplant devices used to artificially shunt aqueous humor out of the eye in glaucoma as well as improve long-term filtering performance of the implant.
1% solution applied to the affected eye three times daily.

Versand/Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Inkompatibilitäten

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explo sions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, methotrexrate sodium, sources of heat.

Fluoruracil Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Fluoruracil Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 576)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
China Synchem Technology Co.,Ltd.
0552-4929304
0552-4928800 sales@cnsynchem.com CHINA 38 55
Yunbio Tech Co.,Ltd.
010-60605551
010-60605551 yunbiochem@126.com CHINA 258 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22625 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile
+86-571-56059825 fandachem@gmail.com CHINA 3268 55
Shanghai Yingrui Biopharma Co., Ltd.
+86-21-33585366 E-mail:sales03@shyrchem.com
+86-21-34979012 sales03@shyrchem.com CHINA 739 60
Anhui Royal Chemical Co., Ltd.
+86-025-86655873
marketing@royal-chem.com CHINA 537 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 30043 58
Zhejiang ZETian Fine Chemicals Co. LTD
+86-18957127338
QQ:800182836 stella@zetchem.com CHINA 2886 58
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 968 58
Shenzhen Nexconn Pharmatechs Ltd
15013857715
admin@nexconn.com CHINA 3000 58

51-21-8(Fluoruracil)Verwandte Suche:


  • 5-Fluorouracil (Abemaciclib Mesylate)
  • 5-FL
  • uorouraciL
  • 5-fluor-2,4(1h,3h)-pyrimidindion
  • 5-Fluor-2,4-dihydroxypyrimidin
  • 5-Fluor-2,4-pyrimidindiol
  • 5-Fluoracil
  • 5-fluoropyrimidin-2,4-diol
  • 5-fluoro-uraci
  • 5-Fluoruracil
  • 5-Ftouracyl
  • Adrucil
  • Arumel
  • Carzonal
  • cincofu
  • Effluderm
  • Effluderm (free base)
  • effluderm(freebase)
  • Efudex
  • Efudix
  • Efurix
  • Fluoroblastin
  • nsc-19893
  • phthoruracil
  • Queroplex
  • Ro 2-9757
  • ro2-9757
  • Timazin
  • U-8953
  • Ulup
  • Uracil, 5-fluoro-
  • 2,4-Dihydroxy-5-fluoropyrimidine, 5-Fluoro-2,4(1H,3H)-pyrimidinedione, 5-FU
  • 2,4-Dihydroxy-5-fluoropyrimidine, 5-Fluoro-2,4(1H,3H)-pyrimidinedione, 5-Fluorouracil, 5-FU
  • 5-FLUOROURACIL
  • 5-FLUOROPYRIMIDINE-2,4(1H,3H)-DIONE
  • 5-Fluoropyrimidine-2,4-dione
  • 5-FU
  • 5-FLUORO-1H-PYRIMIDINE-2,4-DIONE
  • 5-FLUORO-2,4(1H,3H)-PYRIMIDINEDIONE
  • 5-FLUORO-2,4-DIHYDROXYPYRIMIDINE
  • 5-fluoro-2,4-pyrimidinedione
  • 5-Fluor
  • Fluorouracil (USAN)
  • Uracil, 5-fluoro- (VAN 8CI)
  • Sodium cyanoborohydr
  • 5-Fiuorouracil
  • 5-Fluorouracil,2,4-Dihydroxy-5-fluoropyrimidine, 5-FU, 5-Fluoro-2,4(1H,3H)-pyrimidinedione
  • Fluorouracil (250 mg)H2D1901.000mg/mg(dr)
  • Fluorouracil (250 mg)
  • 5-Fluoro-
  • Fluorouracil COS
  • 5-Fluorouracil API
  • 5-FLUOROURACIL FOR SYNTHESIS 5 G
  • Fluorouracil (Adrucil)
  • 5-Fluorouracil, 99% 1GR
  • 5-Fluorouracil - CAS 51-21-8 - Calbiochem
  • [180]-5-Fluorouracil
  • 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-
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