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Cytarabine

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Name

Cytarabine

EINECS 205-705-9
CAS No. 147-94-4 Density 1.89 g/cm3
PSA 130.83000 LogP -1.98180
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 N/A 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 Molecular Structure of 147-94-4 (Cytarabine) Hazard Symbols HarmfulXn, IrritantXi
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;

Article Data 61

Cytarabine Synthetic route

6742-07-0

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine

147-94-4

arabinosyl cytosine

Conditions
ConditionsYield
With ammonia at 25℃;88%
With ammonia for 16h; Ambient temperature; Yield given;
10212-25-6

ancitabine hydrochloride

147-94-4

arabinosyl cytosine

Conditions
ConditionsYield
In ethanol; water83%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant;

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.

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