Basic information
- CAS
320-67-2- Standard SMILES
Nc1ncn(C2OC(CO)C(O)C2O)c(=O)n1- InChIKey
NMUSYJAQQFHJEW-UHFFFAOYSA-N- Molecular formula
- C8H12N4O5
- Average molar mass
- 244.2 g/mol
- Monoisotopic mass
- 244.0807695
Overview
See also: Azacytidine (annotation moved to).
Names & identifiers
- Preferred name
- 4-Amino-1-pentofuranosyl-1,3,5-triazin-2(1H)-one
- IUPAC
- 4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
- English name
- 5-Azacytidine
- Molecular formula
- C8H12N4O5
- Molecular weight
- 244.2
Names & synonyms
4-amino-1-pentofuranosyl-1,3,5-triazin-2(1h)-oneRefChem:1070226DTXCID60209012DTXSID20859335Azacytidine, 5-5-ACs-Triazin-2(1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-5-AZACAzacitidine;5-AzaC;LadakamycinCCRIS93; NSC 281272; KymarabineVidaza (Pharmion)Ara AC
Show more names
AZACITIDINEAZACYTIDINEVidazamylosar4-amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one5 AZC5-AZCRLADAKAMYCIN
WR-183027Anitibiotic U 184964-Amino-1-.beta.-D-ribofuranosyl-s-triazin-2(1H)-one4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-oneNeuro_000048Oprea1_6302434-Amino-1-(beta-D-ribofuranosyl)-1,3,5-triazin-2(1H)-oneCHEMBL301216
Database identifiers
- CAS
320-67-2、65886-71-7- PubChem CID
- 1805
- ChEMBL
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 141 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 384
Experimental & physicochemical properties
LogP-2.17
Physicochemical properties
- Melting point
- 226 · 226-232 °C (dec.)(lit.)
- alpha
- 40 · 40 º (C=1, H2O 22 ºC)
- Boiling point
- 387.12 °C · 387.12°C (rough estimate)
- Density
- 1.4287 · 1.4287 (rough estimate)
- refractive index
- 1.659 · 1.6590 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO (up to 25 mg/ml), or in Water (up to 12 mg/ml).
- form
- lyophilized powder
- pka
- 13.46 · 13.46±0.70(Predicted)
- color
- White to Off-white
- biological source
- synthetic (organic)
- Water Solubility
- 0.5 · 0.5-1.0 g/100 mL at 21 ºC
- Merck
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-23
- PPE
- Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- XZ3017500
- hs_code
- 29349990
- Toxicity
- LD50 in mice (mg/kg): 115.9 i.p.; 572.3 orally (Palm, Kensler)
- risk_code
- 45-46-22
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- T
- safety_code
- 53-22-36/37/39-45
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302-H341-H350-H360FD-H372-H410
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 1Carc. 1AMuta. 2Repr. 1BSTOT RE 1
- Precautionary statements
- P202-P260-P264-P273-P301+P312-P308+P313
- Hazardous Substances Data
- 320-67-2(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionAzacytidine also referred to as Azacytidine and 5-azacytidine (brand name: Vidaza) is an anti-cancer chemotherapy medication. The drug is classified as demethylation and antimetabolite agent. Azacytidine acts by inhibiting the growth and proliferation of cancer cells in the body. The drug is indicated for the treatment of specific types of blood cell disorders and bone marrow cancers.
Description5-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.
UsesA potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase
UsesAntineoplastic;'Antimetabolite
Usesantianginal
Uses5-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.
General DescriptionWhite crystalline powder.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…