Products Categories
CAS No.: | 147-94-4 |
---|---|
Name: | Cytarabine |
Article Data: | 61 |
Molecular Structure: | |
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 |
Conditions | Yield |
---|---|
With ammonia at 25℃; | 88% |
With ammonia for 16h; Ambient temperature; Yield given; |
ancitabine hydrochloride
arabinosyl cytosine
Conditions | Yield |
---|---|
In ethanol; water | 83% |
With potassium hydroxide In water for 0.333333h; Ambient temperature; pH=10.3; |
4-azido-ara-C
arabinosyl cytosine
Conditions | Yield |
---|---|
With hydrogen; palladium dichloride In methanol under 2585.7 Torr; for 30h; Ambient temperature; | 21% |
4-Amino-1-((2R,3S,4R,5R)-4-bromo-3-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one; hydrochloride
A
cyclocitidine
B
arabinosyl cytosine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water-d2 for 168h; or 1-(3-iodo-3-deoxy-β-D-xylofuranosyl)cytosine hydrochloride (2c); |
cyclocitidine
arabinosyl cytosine
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; |
[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
arabinosyl cytosine
Conditions | Yield |
---|---|
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant; |
[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
arabinosyl cytosine
Conditions | Yield |
---|---|
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant; |
[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
arabinosyl cytosine
Conditions | Yield |
---|---|
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant; |
[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
arabinosyl cytosine
Conditions | Yield |
---|---|
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant; |
[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
arabinosyl cytosine
Conditions | Yield |
---|---|
With phosphate buffer; water; porcine liver esterase In ethanol at 37℃; Rate constant; |
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.
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. |