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Grundinformationen
- CAS
320-67-2- Standard-SMILES
Nc1ncn(C2OC(CO)C(O)C2O)c(=O)n1- Summenformel
- C8H12N4O5
- Durchschnittliche Molmasse
- 244,2 g/mol
Namen und Bezeichner
- Bevorzugter Name
- 5-Azacytidine
- Lokaler Name
- 2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on
- Englischer Name
- 5-Azacytidine
- Summenformel
- C8H12N4O5
- Molmasse
- 244.2
Namen und Synonyme
AZACITIDINEAZACYTIDINEVidaza5-AZACmylosar4-amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one5-AC5 AZC5-AZCRLADAKAMYCIN
Datenbank-Bezeichner
- CAS
320-67-2、65886-71-7- PubChem CID
- 1805
- ChEMBL
CHEMBL301216
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 226 · 226-232 °C (dec.)(lit.)
- Siedepunkt
- 387.12 °C · 387.12°C (rough estimate)
- Dichte
- 1.4287 · 1.4287 (rough estimate)
- Brechungsindex
- 1.659 · 1.6590 (estimate)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Soluble in DMSO (up to 25 mg/ml), or in Water (up to 12 mg/ml).
- Aggregatzustand
- lyophilized powder
- pka
- 13.46 · 13.46±0.70(Predicted)
- Farbe
- White to Off-white
- Biologische Quelle
- synthetic (organic)
- Wasserlöslichkeit
- 0.5 · 0.5-1.0 g/100 mL at 21 ºC
- Merck
- 14 · 14,887
- BRN
- 620461 · 620461
- Stabilität
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
- InChI
- 1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
- InChIKey
- NMUSYJAQQFHJEW-WGDKFINWSA-N
- SMILES
- NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O
- LogP
- -2.191 · -2.191 (est)
- CAS Datenbank
- 320 · 320-67-2(CAS DataBase Reference)
- EPA chemische Informationen
- Azacitidine (320-67-2)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- F
- 10-23
- wgk
- 3
- hs_code
- 29349990
- RTECS-Nr.
- XZ3017500
- risk_code
- 45-46-22
- Toxizität
- LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler)
- hazard_code
- T
- safety_code
- 53-22-36/37/39-45
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Giftige Stoffe Daten
- 320-67-2(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 1Carc. 1AMuta. 2Repr. 1BSTOT RE 1
Chemie und Industrie
Anwendungen
Beschreibung5-Azacytidine is an analog of the nucleoside cytidine which can be incorporated into DNA and RNA. 5-Azacytidine acts as an epigenetic modifier by incorporating into DNA where it irreversibly binds to DNA methyltransferases, thus inhibiting their activity.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. 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.
Verwenden5-Azacytidine, its incorporation into RNA alters RNA synthesis and processing, and results in inhibition of protein synthesis. It has been used as a cancer chemotherapeutic agent. It is a powerful bacteriostatic, antitumor, and mutagenic agent; it also exhibits immunosuppressive, antimitotic, radioprotective, and virostatic effects.
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