Name: Cytarabine
SKU: 147-94-4

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Basic Information

Molecular Structure:
CAS No.:	147-94-4
Name:	Cytarabine

Formula:	C₉H₁₃N₃O₅
Molecular Weight:	243.219
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;
EINECS:	205-705-9
Density:	1.89 g/cm³
Melting Point:	214 °C
Boiling Point:	545.7 °C at 760 mmHg
Flash Point:	283.8 °C
Solubility:	water: 50 mg/mL, clear, colorless
Appearance:	white or off-white crystalline powder
Hazard Symbols:	Xn, Xi
Risk Codes:	43-63-36/37/38-20/21/22
Safety:	36/37-37/39-36-26
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;

Raw Materials

Downstream Products

69-74-9

62-49-7

66-22-8

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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.

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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History

Specification