Basic information
- CAS
65886-71-7- Standard SMILES
Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1- InChIKey
NMUSYJAQQFHJEW-ARQDHWQXSA-N- Molecular formula
- C8H12N4O5
- Average molar mass
- 244.2 g/mol
- Monoisotopic mass
- 244.0807695
Overview
Fazarabine is an N-glycosyl-1,3,5-triazine that is 4-amino-1,3,5-triazin-2(1H)-one substituted by a beta-D-arabinofuranosyl residue via an N-glycosidic linkage. A synthetic analogue of cytosine arabinoside and 5-azacytidine that incorporates structural features of both compounds, it shows good activity against a variety of transplanted tumors. It has a role as an antineoplastic agent. It is a N-glycosyl-1,3,5-triazine and a nucleoside analogue. It is functionally related to a beta-D-arabinofuranose.
Names & identifiers
- Preferred name
- Fazarabine
- IUPAC
- 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
- English name
- Fazarabine
- Molecular formula
- C8H12N4O5
- Molecular weight
- 244.2
Names & synonyms
FAZARABINE65886-71-7Ara-AC5-Azacytosine arabinosideFazarabinaFazarabinumKymarabineNSC-2812721-beta-D-Arabinofuranosyl-5-azacytosine5V71D8JOKKNSC 281272CHEBI:141077
Show more names
Azacytidine isomer Impurity 144-Amino-1-β-D-arabinofuranosyl-1,3,5-triazin-2(1H)-one1,3,5-Triazin-2(1H)-one, 4-amino-1-β-D-arabinofuranosyl-Chlorcyclizine Hydrochloride (Chlorcyclizine EP Impurity A )4-Amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
1-beta-D-arabinosyl-5-azacytosine1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-arabinofuranosyl-DTXSID4010243604-Amino-1-beta-D-arabinofuranosyl-1,3,5-triazin-2(1H)-onearabinofuranosyl-5-azacytosineara-5-azacytosineara-5-aza-CydRefChem:598815
Database identifiers
- CAS
65886-71-7
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
Solubility
Water > 16 (mg/mL)
Ethanol insoluble (mg/mL)
Dimethylsulfoxide > 165 (mg/mL)
Optical Rotation(c = 1.2, H2O) [a]25D = 121.5 ± 2
Physicochemical properties
- Melting point
- 220 °C · 220 °C (decomp)
- Boiling point
- 534.5 · 534.5±60.0 °C(Predicted)
- Density
- 2.08 · 2.08±0.1 g/cm3(Predicted)
- pka
- 13.46 · 13.46±0.70(Predicted)
- NCI Dictionary of Cancer Terms
- fazarabine
- FDA UNII
- 5 V71D8JOKK · 5V71D8JOKK
- NCI Drug Dictionary
- fazarabine
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit or prevent the proliferation of NEOPLASMS.
Applications
UsesAntineoplastic.
Suppliers20 total
济南百隆化学有限公司[email protected] · [email protected]
怀化元研达生物技术有限责任公司18711085600 · [email protected]
湖北瑞玛标物科技有限公司15787879035 15787875101 · [email protected]
怀化元研达生物技术有限责任公司18711085600; 18229999901 · [email protected]
杭州璟皓生物科技有限公司（原河南辛迪加生物）17513242016 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
台州南峰药物研究所[email protected] 13127117265 · [email protected]
TLC梯尔希（南京）药物研发有限公司18012923235 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
BOC Sciences16314854226; +8616314854226 · [email protected]
上海一飞生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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