Cytarabine hydrochloride

Base Information

• Chemical Name: Cytarabine hydrochloride
• CAS No.: 69-74-9
• Molecular Formula: C9H13N3O5^.HCl
• Molecular Weight: 279.68
• Hs Code.: 29389090
• European Community (EC) Number: 200-713-9
• UNII: 33K3DB6591
• DSSTox Substance ID: DTXSID5024891
• Wikidata: Q27256279
• NCI Thesaurus Code: C71603
• ChEMBL ID: CHEMBL1256472
• Mol file: 69-74-9.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 hydrochloride

Chemical Property:

• Appearance/Colour: fluffy white powder
• Vapor Pressure: 3.5E-14mmHg at 25°C
• Melting Point: 197-198 °C(lit.)
• Boiling Point: 545.7 °C at 760 mmHg
• Flash Point: 283.8 °C
• PSA: 130.83000
• LogP: -1.17980
• Storage Temp.: 2-8°C
• Solubility.: insoluble in EtOH; ≥14.2 mg/mL in DMSO; ≥64.2 mg/mL in H2O
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 279.0621982
• Heavy Atom Count: 18
• Complexity: 383

Purity/Quality:

99% ^*data from raw suppliers

Cytosine-b-D-arabinofuranoside hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36-43-63
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CN(C(=O)N=C1N)C2C(C(C(O2)CO)O)O.Cl
• Isomeric SMILES: C1=CN(C(=O)N=C1N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O.Cl
• Recent ClinicalTrials: A Study of Bisantrene Combined With Cytarabine or With Decitabine for Adult Subjects With Extramedullary AML and MDS
• Recent EU Clinical Trials: Decitabine-cytarabine chemotherapy in elderly AML and high risk MDS patients (> 65 years) with high early mortality risk
• Description: Cytosine beta-D-arabinofuranoside Hydrochloride is the salt form of Cytarabine, which is a selective inhibitor of DNA synthesis and is used as an antineoplastic and antiviral. Cytosine beta-D-arabinofuranoside Hydrochloride is used in chemotherapy for the treatment of white blood cells cancers such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma.
• Uses: Antiviral. Interferes with the synthesis of DNA
• Therapeutic Function: Cancer chemotherapy

Technology Process of Cytarabine hydrochloride

There total 3 articles about Cytarabine hydrochloride 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: 96.0%

arabinosyl cytosine (147-94-4) → cytarabine hydrochloride (69-74-9,29363-79-9)

Guidance literature:

With hydrogenchloride; In methanol; at 2 - 25 ℃; for 4h;

Reference yield: 62.4%

ancitabine hydrochloride (10212-25-6) → cytarabine hydrochloride (69-74-9,29363-79-9)

Guidance literature:

With ammonia; In water; at 80 ℃; for 0.5h; Temperature;

Reference yield:

→ cytarabine hydrochloride (69-74-9,29363-79-9)

Guidance literature:

upstream raw materials:

arabinosyl cytosine

ancitabine hydrochloride

Downstream raw materials:

(4S)-5'-O-cis-[4-(pyridin-4yl)-2-oxido-1,3,2-dioxaphosphorinan-2yl]-cytosine-β-D-arabinofuranoside

5'-Octanoyl-ara-cytidin

benzyl 1-(3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-ylcarbamate

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

Refernces

• 1、 -. "PROTEIN BINDING COMPOUNDS". Page/Page column 20-21. . Retrieved 2010/02/11.
• 2、 -. "Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents". . . Retrieved 2008/06/13.