Cytarabine

Base Information

• Chemical Name: Cytarabine
• CAS No.: 147-94-4
• Molecular Formula: C9H13N3O5
• Molecular Weight: 243.219
• Hs Code.: PRICE
• European Community (EC) Number: 205-705-9
• UNII: 04079A1RDZ
• DSSTox Substance ID: DTXSID3022877
• Nikkaji Number: J2.958K
• Wikipedia: Cytarabine
• Wikidata: Q180983
• NCI Thesaurus Code: C408
• RXCUI: 3041
• Pharos Ligand ID: AGMYQ3854DM7
• Metabolomics Workbench ID: 43237
• ChEMBL ID: CHEMBL803
• Mol file: 147-94-4.mol

Synonyms:Ara C;Ara-C;Arabinofuranosylcytosine;Arabinoside, Cytosine;Arabinosylcytosine;Aracytidine;Aracytine;beta Ara C;beta-Ara C;Cytarabine;Cytarabine Hydrochloride;Cytonal;Cytosar;Cytosar U;Cytosar-U;Cytosine Arabinoside

Chemical Property of Cytarabine

Chemical Property:

• Appearance/Colour: white or off-white crystalline powder
• Vapor Pressure: 3.5E-14mmHg at 25°C
• Melting Point: 214 °C
• Refractive Index: 1.756
• Boiling Point: 545.7 °C at 760 mmHg
• PKA: pKa 4.3 (Uncertain)
• Flash Point: 283.8 °C
• PSA: 130.83000
• Density: 1.89 g/cm³
• LogP: -1.98180
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: almost transparency
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 243.08552052
• Heavy Atom Count: 17
• Complexity: 383

Purity/Quality:

98%, ^*data from raw suppliers

Cytarabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 43-63-36/37/38-20/21/22
• Safety Statements: 36/37-37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
• Recent ClinicalTrials: Testing the Use of Steroids and Tyrosine Kinase Inhibitors With Blinatumomab or Chemotherapy for Newly Diagnosed BCR-ABL-Positive Acute Lymphoblastic Leukemia in Adults
• Recent EU Clinical Trials: Venetoclax plus Azacitidine versus Standard intensive Chemotherapy for Patients with newly diagnosed Acute Myeloid Leukemia (AML) and NPM1 Mutations eligible for intensive Treatment (VINCENT)
• Recent NIPH Clinical Trials: The novel induction therapy by low-dose cytarabine and blinatumomab for relapse/refractory ALL
• Description: Cytarabine (147-94-4) is a nucleoside analog that interferes with DNA synthesis and transcription, particularly in tumor cells.1,2 Cellular enzymes convert it to its nucleotide form, Ara-CTP, which disrupts DNA and RNA synthesis when polymerases attempt to incorporate it.3,4 For the same reasons, it is also employed as an antiviral.5 It inhibits proliferation of a variety of leukemic cell lines (IC50s 16-72 nM), but is used primarily against acute myeloid leukemia (AML).6
• Uses: Used as an antineoplastic and antiviral. A selective inhibitro of DNA synthesis. Does not inhibit RNA synthesis antineoplastic, antiviral, antimetabolite Cytarabine USP (Cytosar)is used to treat Acute granulocytic leukemia (adults); acute lymphocytic leukemia (children); Hodgkin’s disease
• Indications: Cytarabine (cytosine arabinoside, ara-C, Cytosar-U) is an analogue of the pyrimidine nucleosides cytidine and deoxycytidine. It is one of the most active agents available for the treatment of acute myelogenous leukemia. Cytarabine kills cells in the S-phase of the cycle by competitively inhibiting DNA polymerase. The drug must first be activated by pyrimidine nucleoside kinases to the triphosphate nucleotide ara-cytosine triphosphate (ara-CTP). The susceptibility of tumor cells to cytarabine is thought to be a reflection of their ability to activate the drug more rapidly (by kinases) than to inactivate it (by deaminases).
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Cytarabine is used in the chemotherapy of acute myelogenous leukemia, usually in combination with an anthracycline agent, thioguanine, or both. It is less useful in acute lymphoblastic leukemia and the lymphomas and has no known activity against other tumors. It has been used intrathecally in the treatment of meningeal leukemias and lymphomas as an alternative to methotrexate.
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid with clozapine, increased risk of agranulocytosis.

Technology Process of Cytarabine

There total 52 articles about Cytarabine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

1-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)cytosine (6742-07-0) → arabinosyl cytosine (147-94-4)

Guidance literature:

With ammonia; at 25 ℃;

DOI:10.1016/0040-4020(96)00289-X

Reference yield: 83.0%

ancitabine hydrochloride (10212-25-6) → arabinosyl cytosine (147-94-4)

Guidance literature:

In ethanol; water;

Reference yield: 21.0%

4-azido-ara-C (196706-06-6) → arabinosyl cytosine (147-94-4)

Guidance literature:

With hydrogen; palladium dichloride; In methanol; for 30h; under 2585.7 Torr; Ambient temperature;

DOI:10.1021/jo970761t

upstream raw materials:

ancitabine hydrochloride

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

cyclocitidine

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

Downstream raw materials:

1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-imino-5-phenylselanyl-3,4-dihydro-1H-pyrimidin-2-one

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

N⁴-benzoyl-5'-O-monomethoxytritylarabinocytidine

N⁴-benzoyl-5'-O-monomethoxytritylarabinocytidine-3'-O-N,N-diiso-propyl-β-cyanoethylphosphoramidite

Refernces

• 1、 Fromageot,Reese. "-". . p. 3499,3500. Retrieved 1966.
• 2、 Ogilvie. "-". . p. 210. Retrieved 1972.
• 3、 Hirata, Nao,Fujisawa, Yusuke,Tanabe, Kazuhito,Harada, Hiroshi,Hiraoka, Masahiro,Nishimoto, Sei-Ichi. "Radiolytic activation of a cytarabine prodrug possessing a 2-oxoalkyl group: One-electron reduction and cytotoxicity characteristics". . p. 651 - 654. Retrieved 2009.
• 4、 Moris,Gotor. "Enzymatic acylation and alkoxycarbonylation of α-, xylo-, anhydro-, and arabino-nucleosides". . p. 10089 - 10098. Retrieved 1993.
• 5、 -. "BIOCATALYTIC PRODUCTION OF NUCLEOSIDE ANALOGUES AS ACTIVE PHARMACEUTICAL INGREDIENTS". Paragraph 0238. . Retrieved 2016/04/09.
• 6、 -. "THERAPEUTIC FOR HEPATIC CANCER". . . Retrieved 2011/02/18.