Cytarabine supplier | CasNO.147-94-4

Name
Cytarabine
EINECS 205-705-9
CAS No. 147-94-4
Article Data61
CAS DataBase
Density 1.89 g/cm³
Solubility water: 50 mg/mL, clear, colorless
Melting Point 214 °C
Formula C₉H₁₃N₃O₅
Boiling Point 545.7 °C at 760 mmHg
Molecular Weight 243.219
Flash Point 283.8 °C
Transport Information
Appearance white or off-white crystalline powder
Safety 36/37-37/39-36-26
Risk Codes 43-63-36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms 2(1H)-Pyrimidinone,4-amino-1-a-Darabinofuranosyl-;U-19,920;Cytosine Arabinoside;cytarbine;Depocyt (liposomal);Arafcyt;Cytosine, 1-beta-D-arabinofuranosyl-;Cytosine-1-beta-arabinofuranoside;Depocyt (TN);Cytosine beta-D-arabinofuranoside;Erpalfa;Arabitin;Tarabine PFS;ara-Cytosine;Cytarabin;1.beta.-D-Arabinofuranosylcytosine;Udicil;NCI-C04728;.beta.-Cytosine arabinoside;Cytosar U;Aracytin;1-(beta,D-Arabinofuranosyl)cytosine;Cyclocide;2(1H)-Pyrimidinone, 4-amino-1.beta.-D-arabinofuranosyl-;1beta-D-Arabinosylcytosine;Arabinofuranosylcytosine;
PSA 130.83000
LogP -1.98180

Synthetic route

: 6742-07-0
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With ammonia at 25℃;	88%
With ammonia for 16h; Ambient temperature; Yield given;

: 10212-25-6
ancitabine hydrochloride

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
In ethanol; water	83%
With potassium hydroxide In water for 0.333333h; Ambient temperature; pH=10.3;

: 196706-06-6
4-azido-ara-C

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With hydrogen; palladium dichloride In methanol under 2585.7 Torr; for 30h; Ambient temperature;	21%

: 74580-91-9
4-Amino-1-((2R,3S,4R,5R)-4-bromo-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one; hydrochloride

A: 31698-14-3
cyclocitidine

B: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water-d2 for 168h; or 1-(3-iodo-3-deoxy-β-D-xylofuranosyl)cytosine hydrochloride (2c);

: 31698-14-3
cyclocitidine

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 1h; Heating; Yield given;
With water In various solvent(s) at 40℃; Rate constant; other reagents, solvents;

: 170935-57-6
[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid methyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-58-7
[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid ethyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-59-8
[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid propyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-60-1
[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid 2-methoxy-ethyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 81691-79-4
[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-carbamic acid octyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-63-4
benzyl 1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-65-6
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid methyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-66-7
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid ethyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-67-8
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid propyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-68-9
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid pentyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-69-0
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid octyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-70-3
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid benzyl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: 170935-62-3
C37H57N3O7

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

: (S)-2-Amino-3-(4-benzyloxy-phenyl)-N-{1-[1-((2R,3S,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-1-methyl-ethyl}-propionamide; hydrochloride

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With d(4)-methanol at 22℃; the rate of release of ara-C; other ara-C derivatives, other reagents, var. pH;

: 170935-70-3
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid benzyl ester

A: 103-40-2
succinic acid monobenzyl ester

B: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium carbonate at 25℃; Rate constant; various pH;

<(3aS)-2t-hydroxymethyl-6-imino-(3ar,9ac)-2,3,3a,9a-tetrahydro-6H-furo<2',3':4,5>oxazolo<3,2-a>pyrimidin-3c-ol: <(3aS)-2t-hydroxymethyl-6-imino-(3ar,9ac)-2,3,3a,9a-tetrahydro-6H-furo<2',3':4,5>oxazolo<3,2-a>pyrimidin-3c-ol

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
With water Hydrolysis.wss.Loesung;

: N4-(1-(5-nitrothien-2-yl)ethyl)oxycarbonyl-1-β-D-arabinofuranosylcytosine

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
In water; isopropyl alcohol G-values; Irradiation;

: 3083-77-0
araU

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 2.) 4-chlorophenyl dichlorophosphate / 1.) pyridine, 0 deg C, 12 h, 2.) pyridine, room temperature, 24 h 2: LiN3 / dimethylformamide / 3 h / 50 °C 3: 72 percent / 1N HCl / methanol / 26 h / Ambient temperature 4: 21 percent / H2 / PdCl2 / methanol / 30 h / 2585.7 Torr / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 34.7 g / pyridine / 5 h / Ambient temperature 2: 89 percent / acetonitrile / 1.5 h / Ambient temperature 3: aq.ammonia / dioxane / 6 h / Ambient temperature 4: methanolic ammonia / 16 h / Ambient temperature View Scheme

: 82855-62-7
4-(1,2,4-triazol-1-yl)-1-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)pyrimidine-2(1H)one

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: LiN3 / dimethylformamide / 3 h / 50 °C 2: 72 percent / 1N HCl / methanol / 26 h / Ambient temperature 3: 21 percent / H2 / PdCl2 / methanol / 30 h / 2585.7 Torr / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: aq.ammonia / dioxane / 6 h / Ambient temperature 2: methanolic ammonia / 16 h / Ambient temperature View Scheme

: 196706-05-5
Acetic acid (2R,3S,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-azido-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / 1N HCl / methanol / 26 h / Ambient temperature 2: 21 percent / H2 / PdCl2 / methanol / 30 h / 2585.7 Torr / Ambient temperature View Scheme

: 25130-27-2
2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl-4-thiouridine

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / dimethyldioxirane, NH3 / acetone; CH2Cl2 / 25 °C 2: 88 percent / 2N methanol. NH3 / 25 °C View Scheme

: 3736-77-4
2,2'-Anhydrouridine

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: triethylamine / H2O / 5 h / 70 °C 2: 34.7 g / pyridine / 5 h / Ambient temperature 3: 89 percent / acetonitrile / 1.5 h / Ambient temperature 4: aq.ammonia / dioxane / 6 h / Ambient temperature 5: methanolic ammonia / 16 h / Ambient temperature View Scheme

: 58-96-8
uridine

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: diphenyl carbonate, sodium hydrogen carbonate / hexamethylphosphoric acid triamide / 0.33 h / 150 °C 2: triethylamine / H2O / 5 h / 70 °C 3: 34.7 g / pyridine / 5 h / Ambient temperature 4: 89 percent / acetonitrile / 1.5 h / Ambient temperature 5: aq.ammonia / dioxane / 6 h / Ambient temperature 6: methanolic ammonia / 16 h / Ambient temperature View Scheme

: 14057-18-2
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)uracil

: 147-94-4
arabinosyl cytosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 89 percent / acetonitrile / 1.5 h / Ambient temperature 2: aq.ammonia / dioxane / 6 h / Ambient temperature 3: methanolic ammonia / 16 h / Ambient temperature View Scheme

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 147-94-4
arabinosyl cytosine

: 60342-57-6
N4-<(dimethylamino)methylene>arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	100%
In N,N-dimethyl-formamide	100%

: 108-24-7
acetic anhydride

: 147-94-4
arabinosyl cytosine

: 6742-08-1
N4-acetyl-1-<2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl>cytosine

Conditions

Conditions	Yield
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 8h;	100%

: 147-94-4
arabinosyl cytosine

: 3083-77-0
araU

Conditions

Conditions	Yield
With cytidine deaminase enzyme In aq. phosphate buffer at 37℃; for 0.0833333h; pH=7; Enzymatic reaction;	99%
cytidine deaminase ( EC 3.5.4.5 ) at 37℃; for 48h; pH=6.8 with acetic acid;
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products;

: 69304-37-6
1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

: 147-94-4
arabinosyl cytosine

: 75331-99-6
1-[3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]cytosine

Conditions

Conditions	Yield
In pyridine for 1h; Ambient temperature;	98%
With pyridine at 20℃; for 4h;	90%
With pyridine at 25℃; for 2h;	70%
In pyridine for 3h; Ambient temperature;

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147-94-4
arabinosyl cytosine

: 90362-54-2
1-[2',3',5'-tris-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

Conditions

Conditions	Yield
With pyridine; silver nitrate; triethylamine In tetrahydrofuran at 20℃; for 26h; silylation;	98%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 63℃; Cooling with ice; Inert atmosphere;	90%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;	85%

: 75-36-5
acetyl chloride

: 147-94-4
arabinosyl cytosine

: 58227-71-7
1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine hydrochloride

Conditions

Conditions	Yield
With acetic acid In chloroform	96%

: 147-94-4
arabinosyl cytosine

: 69-74-9
cytarabine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 2 - 25℃; for 4h;	96%
With hydrogenchloride In diethyl ether

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 147-94-4
arabinosyl cytosine

: N 4-( N,N-dimethylaminomethylene)cytarabine

Conditions

Conditions	Yield
In ethanol at 65℃; for 4h;	96%

: 76-83-5
trityl chloride

: 147-94-4
arabinosyl cytosine

: 7075-13-0
1-(5'-o-trityl-β-D-arabinofuranosyl)cytosine

Conditions

Conditions	Yield
With pyridine at 20℃; for 20h; Inert atmosphere; regioselective reaction;	95.2%
With pyridine In water at 30℃; for 22h; Inert atmosphere;	95.2%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 147-94-4
arabinosyl cytosine

: 82845-90-7
4-Amino-1-{(2R,3S,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one

Conditions

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at -5℃; for 1h;	95%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147-94-4
arabinosyl cytosine

: 82845-96-3
1-[3',5'-di(O-tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

Conditions

Conditions	Yield
With 3-picoline-N-oxide; silver nitrate In tetrahydrofuran for 2h; Ambient temperature;	95%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 14h;	92%
With 1H-imidazole In N,N-dimethyl-formamide; toluene at -5 - 5℃;

: 219797-98-5
3-Acryloylamino-propionic acid pentafluorophenyl ester

: 147-94-4
arabinosyl cytosine

: 186594-89-8
N-{2-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-ylcarbamoyl]-ethyl}-acrylamide

Conditions

Conditions	Yield
With TEA In pyridine at 80℃; for 12h;	95%

: 93-97-0
benzoic acid anhydride

: 147-94-4
arabinosyl cytosine

: 16640-05-4
1-(β-D-arabinofuranosyl)-N4-benzoylcytosine

Conditions

Conditions	Yield
In ethanol for 4h; Heating;	95%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147-94-4
arabinosyl cytosine

: 82976-97-4
1-[5'-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

Conditions

Conditions	Yield
With pyridine; 1H-imidazole at 20℃; for 3h;	95%
With pyridine Cooling with ice; Inert atmosphere;	85.4%
With pyridine; 1H-imidazole In 1,4-dioxane

: 19449-28-6
N,N-diisopropylformamide dimethyl acetal

: 147-94-4
arabinosyl cytosine

: N4-<(diisopropylamino)methylene>arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	93%
In N,N-dimethyl-formamide	93%

: 17508-17-7
O-(2,4-dinitrophenyl)hydroxylamine

: 147-94-4
arabinosyl cytosine

: 88685-83-0
3-amino-1-β-D-arabinofuranosylcytosine hydrochloride

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 12h; Ambient temperature;	93%

: 19449-31-1
N-(dimethoxymethyl)morpholine

: 147-94-4
arabinosyl cytosine

: N4-(morpholinomethylene)arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	93%
In N,N-dimethyl-formamide	93%

: 201210-74-4
Succinic acid 5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl ester pentafluorophenyl ester

: 147-94-4
arabinosyl cytosine

: 201210-76-6
N-[1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-succinamic acid 5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 72h; Ambient temperature;	93%

: 4432-76-2
N,N-diethylformamide dimethylacetal

: 147-94-4
arabinosyl cytosine

: N4-<(diethylamino)methylene>arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	90%
In N,N-dimethyl-formamide	90%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 147-94-4
arabinosyl cytosine

A: 82845-96-3
1-[3',5'-di(O-tert-butyldimethylsilyl)-β-D-arabinofuranosyl]cytosine

B: 82845-92-9
4-Amino-1-[(2R,3S,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidin-2-one

Conditions

Conditions	Yield
With 4-methylpyridine-1-oxide; silver nitrate In 1,2-dimethoxyethane for 2h;	A 90% B 5%
With silver nitrate; triethylamine In 1,2-dimethoxyethane for 3h; Ambient temperature;	A 5% B 90%
With triethylamine; silver nitrate In 1,2-dimethoxyethane for 3h;	A 5% B 90%

...Expand

: 14470-28-1
mono-4-methoxytrityl chloride

: 147-94-4
arabinosyl cytosine

: 87418-74-4
4-Amino-1-{(2R,3S,4S,5R)-3,4-dihydroxy-5-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-tetrahydro-furan-2-yl}-1H-pyrimidin-2-one

Conditions

Conditions	Yield
With pyridine at 50℃;	90%
With pyridine for 22h; Ambient temperature;	79%

: 5564-73-8
1-(dimethoxymethyl)pyrrolidine

: 147-94-4
arabinosyl cytosine

: N4-(pyrrolidinomethylene)arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	89%
In N,N-dimethyl-formamide	89%

: 128-13-2
ursodeoxycholic acid

: 147-94-4
arabinosyl cytosine

: (4R)-N-(1-((3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-furan-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)-(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide

Conditions

Conditions	Yield
Stage #1: ursodeoxycholic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at -15℃; for 0.25h; Inert atmosphere; Stage #2: arabinosyl cytosine With triethylamine In N,N-dimethyl-formamide at -15 - 20℃; for 0.5h; Inert atmosphere;	87%
Stage #1: ursodeoxycholic acid With triethylamine; isobutyl chloroformate In N,N-dimethyl-formamide at -15℃; for 0.0833333h; Stage #2: arabinosyl cytosine With triethylamine In N,N-dimethyl-formamide at -15 - 20℃; for 2.5h;

: 5211-86-9
N-(dimethoxymethyl)piperidine

: 147-94-4
arabinosyl cytosine

: N4-(piperidinomethylene)arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Ambient temperature;	85%
In N,N-dimethyl-formamide at 20℃;	85%

: 5211-95-0
N,N-di-n-propylformamide dimethyl acetal

: 147-94-4
arabinosyl cytosine

: N4-<(dipropylamino)methylene>arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 8h; Ambient temperature;	85%
In N,N-dimethyl-formamide	85%

: 19449-30-0
N,N-dibutylformamide dimethyl acetal

: 147-94-4
arabinosyl cytosine

: 908340-60-3
N4-[(dibutylamino)methylidene]arabinocytidine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide	85%

: 147-94-4
arabinosyl cytosine

O\-methyl-poly(ethylene glycol)-lysyl-OSu, PEG part Mw 10000 Da; Su: N-succinimido: O\-methyl-poly(ethylene glycol)-lysyl-OSu, PEG part Mw 10000 Da; Su: N-succinimido

O-methyl-poly(ethylene glycol)-lysyl-(1-β-D-arabinofuranosylcytosin-N4-yl), PEG part Mw 10000 Da: O-methyl-poly(ethylene glycol)-lysyl-(1-β-D-arabinofuranosylcytosin-N4-yl), PEG part Mw 10000 Da

Conditions

Conditions	Yield
With pyridine at 20℃; for 72h;	83%

: 3303-84-2
3-(tert-butyloxycarbonylamino)propionic acid

: 147-94-4
arabinosyl cytosine

: 474083-71-1
tert-butyl 3-(1-((3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-ylamino)-3-oxopropylcarbamate

Conditions

Conditions	Yield
Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With chloroformic acid ethyl ester; triethylamine In N,N-dimethyl-formamide at -15℃; for 0.5h; Stage #2: arabinosyl cytosine In N,N-dimethyl-formamide at -15 - 20℃;	82%

Cytarabine History

Cytarabine was discovered in Europe in the 1960s. It was approved by the United States Food and Drug Administration in June 1969, and was initially marketed in the US by Upjohn under the trade name Cytosar-U.

Cytarabine Specification

The IUPAC name of Cytarabine is 4-amino-1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one. With the CAS registry number 147-94-4, it is also named as 1-Arabinofuranosylcytosine. The product's categories are Active Pharmaceutical Ingredients; API Intermediates; Antivirals for Research and Experimental Use; Biochemistry; Chemical Reagents for Pharmacology Research; Nucleosides, Nucleotides & Related Reagents; Carbohydrates & Derivatives; Nucleotides. It is white or off-white crystalline powder which is toxic and flammable. It will produce toxic nitrogen oxide fumes when buring. So the storage environment should be well-ventilated, low-temperature and dry. Keep Cytarabine separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.94; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.94; (4)ACD/LogD (pH 7.4): -1.94; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.1; (8)ACD/KOC (pH 7.4): 2.11; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.756; (13)Molar Refractivity: 52.64 cm³; (14)Molar Volume: 128.4 cm³; (15)Polarizability: 20.86×10^-24 cm³; (16)Surface Tension: 89.5 dyne/cm; (17)Enthalpy of Vaporization: 94.8 kJ/mol; (18)Vapour Pressure: 3.5E-14 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 3; (21)Exact Mass: 243.085521; (22)MonoIsotopic Mass: 243.085521; (23)Topological Polar Surface Area: 129; (24)Heavy Atom Count: 17; (25)Complexity: 383.

Preparation of Cytarabine: First, we can get cytidine from the hydrolysis of 5-cytidylic acid. Then we get the product after chlorination, epoxidation, hydrolysis in ammonia and salting.

Uses of Cytarabine: It is a pyrimidine nucleoside analog that is used mainly in the treatment of leukemia, especially acute non-lymphoblastic leukemia.And it is also an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. What's more, it also has antiviral and immunosuppressant properties. One of the unique toxicities of cytarabine is cerebellar toxicity when given in high doses. In addition, it can be used to produce 4-amino-1-[2-hydroxy-1-(2-hydroxy-1-hydroxymethyl-ethoxy)-ethyl]-1H-pyrimidin-2-one. This reaction needs reagents NaIO₄ and NaBH₄ supporting Amberlyst A-27 and solvent water. The yield is 79%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. And it also has possible risk of harm to the unborn child. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C1/N=C(/N)\C=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO
2. InChI:InChI=1/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8-/m1/s1
3. InChIKey:UHDGCWIWMRVCDJ-XVFCMESIBD

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	intravenous	33200ug/kg/24 (33.2mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Cancer Vol. 42, Pg. 53, 1978.
human	TDLo	intravenous	17241mg/kg/6D (17241mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"	Annals of Internal Medicine. Vol. 102, Pg. 556, 1985.
man	LDLo	intravenous	1536mg/kg/43W (1536mg/kg)	PERIPHERAL NERVE AND SENSATION: FASCICULATIONS BEHAVIORAL: ATAXIA	Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 177, 1987.
man	TDLo	intraspinal	11429ug/kg (11.429mg/kg)	PERIPHERAL NERVE AND SENSATION: PARESTHESIS	Journal of Toxicology, Clinical Toxicology. Vol. 38, Pg. 246, 2000.
man	TDLo	intravenous	23500ug/kg/7D (23.5mg/kg)	SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE	American Journal of Ophthalmology. Vol. 113, Pg. 587, 1992.
man	TDLo	intravenous	649mg/kg/4D-I (649mg/kg)	PERIPHERAL NERVE AND SENSATION: FASCICULATIONS	Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 177, 1987.
man	TDLo	subcutaneous	60mg/kg/90W-I (60mg/kg)	SENSE ORGANS AND SPECIAL SENSES: CHANGE IN ACUITY: EAR BEHAVIORAL: ATAXIA BLOOD: CHANGES IN SPLEEN	Drug Intelligence and Clinical Pharmacy. Vol. 21, Pg. 798, 1987.
mouse	LD50	intraperitoneal	3779mg/kg (3779mg/kg)		Cancer Research. Vol. 39, Pg. 2204, 1979.
mouse	LD50	intravenous	> 7gm/kg (7000mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
mouse	LD50	oral	3150mg/kg (3150mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
mouse	LD50	subcutaneous	> 10gm/kg (10000mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
rat	LD50	intraperitoneal	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
rat	LD50	intravenous	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
rat	LD50	subcutaneous	> 5gm/kg (5000mg/kg)		Drugs in Japan Vol. 6, Pg. 321, 1982.
women	TDLo	intravenous	720mg/kg/3D-I (720mg/kg)	BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES	Neurology. Vol. 35, Pg. 1475, 1985.
women	TDLo	subcutaneous	6480ug/kg/12D (6.48mg/kg)	BLOOD: OTHER CHANGES	New England Journal of Medicine. Vol. 310, Pg. 1328, 1984.

Product Name

Cytarabine

Synthetic route

Cytarabine History

Cytarabine Specification

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