2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on Produkt Beschreibung

5-Azacytidine Struktur
320-67-2
  • CAS-Nr.320-67-2
  • Bezeichnung:2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on
  • Englisch Name:5-Azacytidine
  • Synonyma:2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on
    AzGR;5-AC;5 AZC;Vidaza;u18496;5-AZAC;5-AZCR;mylosar;5-AC-15N4;wr 183027
  • CBNumber:CB4383338
  • Summenformel:C8H12N4O5
  • Molgewicht:244.2
  • MOL-Datei:320-67-2.mol
2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on physikalisch-chemischer Eigenschaften
  • Schmelzpunkt: :226-232 °C (dec.)(lit.)
  • alpha  :40 º (C=1, H2O 22 ºC)
  • Siedepunkt: :387.12°C (rough estimate)
  • Dichte :1.4287 (rough estimate)
  • Brechungsindex :1.6590 (estimate)
  • storage temp.  :2-8°C
  • Aggregatzustand :lyophilized powder
  • Farbe :White to Off-white
  • Wasserlöslichkeit :0.5-1.0 g/100 mL at 21 ºC
  • Merck  :14,887
  • BRN  :620461
  • InChIKey :NMUSYJAQQFHJEW-WGDKFINWSA-N
  • CAS Datenbank :320-67-2(CAS DataBase Reference)
  • EPA chemische Informationen :1,3,5-Triazin-2( 1H)-one, 4-amino-1-.beta.-D-ribofuranosyl- (320-67-2)
Sicherheit

5-Azacytidine Chemische Eigenschaften,Einsatz,Produktion Methoden

  • R-Sätze Betriebsanweisung: R45:Kann Krebs erzeugen.
    R46:Kann vererbbare Schäden verursachen.
    R22:Gesundheitsschädlich beim Verschlucken.
  • S-Sätze Betriebsanweisung: S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
    S22:Staub nicht einatmen.
    S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
    S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  • Beschreibung Azacitidine is an antineoplastic agent launched for the treatment of myelodysplastic syndrome (MDS). MDS is a group of closely related diseases caused by abnormal blood-forming stem cells of the bone marrow. They are characterized by a hyperproliferative bone marrow, the presence of clonal blood cells with impaired morphology and maturation, and peripheral blood cytopenias resulting from ineffective blood cell production. The initial stem cell injury can be from cytotoxic chemotherapy, radiation exposure, chemical exposure, or genetic predisposition. Subsequently a clonal mutation predominates over bone marrow thereby suppressing healthy stem cells. Azacitidine is indicated for the treatment of all five subtypes of MDS, which consist of refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia. Azacitidine is an analog of cytidine in which the carbon at position 5 of the pyrimidine ring has been replaced by nitrogen. It is prepared by the ribosylation of 5-azacytosine, which is derived from the condensation of amidinourea with either an alkyl orthoformate or N,N-dimethylformamide dialkyl acetal. The antineoplastic activity of azacitidine is derived from a combination of two different mechanisms. It inhibits DNA methyltransferase, which causes demethylation or hypomethylation of DNA. In addition, it exerts direct cytotoxicity on hyperproliferating abnormal stem cells in the bone marrow. After in vivo phosphorylation, azacitidine incorporates into DNA and forms covalent adducts with cellular DNA methyltransferase, thereby depleting the cells from enzyme activity and causing hypomethylation of genomic DNA. Hypomethylation restores normal function to tumor-suppressor genes, which are responsible for regulating cell differentiation and growth. The cytotoxic effects of azacitidine cause the death of rapidly dividing cells, including cancer cells that are no longer responsive to normal growth control mechanisms. Non-proliferating cells are relatively insensitive to azacitidine. The recommended dosage of azacitidine is 75 mg/m2 subcutaneously once daily for 7 days, and the cycle is repeated every 4 weeks. It is rapidly absorbed with peak concentrations achieved within 30 minutes of the dose. It has a bioavailability of 89% and a mean volume of distribution of 76±26 liters. Mean clearance of azacitidine is 167±49 L/hour, and the mean half-life of the parent drug is 41±8 minutes. The primary route of elimination for azacitidine and its metabolites is renal (85%), with a cumulative mean elimination half-life of 4 hours. The efficacy of azacitidine was demonstrated in a randomized, open-label, controlled clinical trial and two non-randomized trials involving 300 patients with any of the five subtypes of MDS. Approximately 14–19% of patients in these trials had an overall response rate (complete response+partial response) to azacitidine, which consisted of normalization of blood counts and decrease in bone marrow blasts percentage. The initial response was generally observed by the fifth cycle of treatment. The need for transfusions was also eliminated in responder patients. In all three studies, approximately 19% of patients met the criteria for improvement with a median duration of 195 days. The most common adverse events with azacitidine therapy include nausea, vomiting, myelosuppression, and infection. Dose-limiting toxicities include neutropenia and thrombocytopenia.
  • Chemische Eigenschaften White-to-Off-White Crystalline Solid
  • Chemische Eigenschaften White crystalline solid or powder.
  • Originator Pharmion (US)
  • Verwenden Antineoplastic;'Antimetabolite
  • Verwenden antianginal
  • Verwenden A potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase
  • Definition ChEBI: A N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-ribofuranosyl residue via a N-glycosidic linkage.
  • Trademarks Vidaza (Pharmion).
  • Allgemeine Beschreibung White crystalline powder.
  • Air & Water Reaktionen Slightly water soluble. Unstable in solution.
  • Reaktivität anzeigen 5-Azacytidine is sensitive to light (may discolor). 5-Azacytidine is sensitive to oxidation. 5-Azacytidine is unstable in solution. 5-Azacytidine undergoes hydrolysis in aqueous buffers. 5-Azacytidine is incompatible with strong oxidizers.
  • Brandgefahr Flash point data for 5-Azacytidine are not available; however, 5-Azacytidine is probably combustible.
  • Biologische Aktivität DNA methyltransferase inhibitor. Incorporates into DNA forming covalent adducts with cellular DNMT1, depleting enzyme activity. Induces demethylation and reactivation of silenced genes. Improves the efficiency of reprogramming of stem cells.
  • Sicherheitsprofil Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Poison by ingestion, intravenous, and intraperitoneal routes. Human systemic effects by intravenous route: nausea, vomiting and dlarrhea, reduction in white cell count (luekopenia and agranulocytosis). An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of NOx.
  • mögliche Exposition A growth inhibitor (DNA methyltransferase inhibitor). A cytotoxic agent and chemotherapeutic agent used to treat angina pectoris, an ischemic heart disease symptom. Occupational exposure to azacitidine could occur among health professionals and support staff (including custodians) by dermal contact, inhalation, or accidental ingestion during drug preparation or administration or cleanup of medical waste, including disposal of excretions from treated patients (Zimmerman et al. 1981, NIOSH 2004). The National Occupational Exposure Survey (conducted from 1981 to 1983) estimated that 1069 healthservices workers, including 698 women, potentially were exposed to azacitidine. Azacitidine may be produced synthetically or isolated from the bacterium Streptoverticillium ladakanus . Incompatibilities: Azacitidine is Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with alkali metals, nitrides, and strong reducing agents such as hydrides may form flammable and/or toxic gases. May react with anhydrides forming acids and esters, generating noticeable heat, and also with oxoacids and carboxylic acids to form esters plus water, but the heat of reaction in the latter case typically is low. Keep away from isocyanates and epoxides; may initiate their polymerization. Azacitidine is sensitive to light and oxidation and unstable in solution. It undergoes hydrolysis in aqueous buffers.
  • Carcinogenicity Azacitidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
  • Versand/Shipping UN3249 Medicine, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
  • Inkompatibilitäten Azacitidine is Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with alkali metals, nitrides, and strong reducing agents such as hydrides may form flammable and/or toxic gases. May react with anhydrides forming acids and esters, generating noticeable heat, and also with oxoacids and carboxylic acids to form esters plus water, but the heat of reaction in the latter case typically is low. Keep away from isocyanates and epoxides; may initiate their polymerization. Azacitidine is sensitive to light and oxidation and unstable in solution. It undergoes hydrolysis in aqueous buffers.
  • Waste disposal It is inappropriate and possibly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quantities of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
  • Verordnung (Regulations) Food and Drug Administration (FDA)
    Azicitidine is regulated as a prescription drug subject to labeling and other requirements.
5-Azacytidine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
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320-67-2, 5-Azacytidine Verwandte Suche:
  • 1,3,5-Triazin-2(1H)-one, 4-aMino-1-β-D-ribofuranosyl-
  • 4-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one Ladakamycin
  • Azacitidine(5-Azacitidine)
  • Azacitidine(Vidaza)
  • 4-aMino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
  • Azacitidine (150 mg)
  • 4-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-1,3,5-triazin-2
  • 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one Ladakamycin
  • 5-AZACYTIDINE extrapure
  • Ladakamycin, 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
  • 4-amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one
  • AzGR
  • antibioticu18496
  • mylosar
  • nci-c01569
  • nsc-102816
  • u18496
  • 5-AZAC
  • 5-AZACYTIDINE
  • 4-AMINO-1-B-D-RIBOFURANOSYL-SYM-TRIAZINE-2(1H)-ONE
  • 4-AMINO-1-BETA-D-RIBOFURANOSYL-5-TRIAZIN-2[1H]-ONE
  • 4-AMINO-1-BETA-D-RIBOFURANOSYL-S-TRIAZIN-2[1H]ONE
  • 4-AMINO-1-(BETA-D-RIBOFURANOSYL)-1,3,5-TRIAZIN-2(1H)-ONE
  • 4-AMINO-1-BETA-D-RIBOFURANOSYL-1,3,5-TRIAZINE-2[1H]-ONE
  • Azacetidine
  • NBC-102816
  • 1,3,5-Triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl-
  • s-Triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl-
  • Vidaza
  • 5-Azacitidine
  • 5-AZACYTIDIN
  • 5-Azacytidine ,98%
  • 5-Azacytidine,4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one, Ladakamycin
  • Azacitidine (5-Azacytidine)
  • 4-aMino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)oxolan-2-yl]-1,2-dihydro-1,3,5-triazin-2-one
  • 5'-azacytidine, β-D-5-azaC, 5-azacytidine, azacitidine, azacytidine, 5-aza-C, 4-aMino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
  • 5-Azacytidine, 99% 50MG
  • LedakaMycin
  • NSC 103-627
  • 4-AMino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one-15N4
  • 5-AC-15N4
  • 5-AzaC-15N4
  • 5-AZC-15N4
  • 5-AZCR-15N4
  • 4-amino-1-beta-d-ribofuranosyl-s-triazin-2(1h)-on
  • 5-triazin-2(1h)-one,4-amino-1-beta-d-ribofuranosyl-3
  • LADAKAMYCIN
  • AZACYTIDINE
  • AZACITIDINE
  • 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
  • 5 AZC
  • 5-AC
  • 5-AZCR
  • wr 183027
  • 2-(beta-D-ribofuranosyl)-4-amino-1,3,5-triazin-2-one
  • 5-AZACYTIDINE (50X) GAMMA-IRRADIATEDCELL CULTURE T
  • 5-AZACYTIDINE CRYSTALLINE
  • 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-t