Cytarabine

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.