Capecitabine

Base Information

• Chemical Name: Capecitabine
• CAS No.: 154361-50-9
• Deprecated CAS: 158798-73-3,958887-39-3
• Molecular Formula: C15H22FN3O6
• Molecular Weight: 359.355
• Hs Code.: 29349990
• UNII: 6804DJ8Z9U
• DSSTox Substance ID: DTXSID3046451
• Nikkaji Number: J949.163E
• Wikipedia: Capecitabine
• Wikidata: Q420207
• NCI Thesaurus Code: C1794
• RXCUI: 194000
• Pharos Ligand ID: MPG47MAK7RQ3
• Metabolomics Workbench ID: 43331
• ChEMBL ID: CHEMBL1773
• Mol file: 154361-50-9.mol

Synonyms:capecitabine;N(4)-pentyloxycarbonyl-5'-deoxy-5-fluorocytidine;Xeloda

Chemical Property of Capecitabine

Chemical Property:

• Appearance/Colour: Colourless solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 110-121 °C
• Refractive Index: 1.7
• Boiling Point: 437.874oC at 760 mmHg
• PKA: 5.41±0.40(Predicted)
• Flash Point: 218.619oC
• PSA: 122.91000
• Density: 1.49 g/cm³
• LogP: 0.83320
• Storage Temp.: -20°C Freezer
• Solubility.: H2O: soluble10mg/mL, clear (warmed)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 359.14926359
• Heavy Atom Count: 25
• Complexity: 582

Purity/Quality:

99% ^*data from raw suppliers

Capecitabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 45-60-61-68
• Safety Statements: 53-22-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CCCCCOC(=O)NC1=NC(=O)N(C=C1F)C2C(C(C(O2)C)O)O
• Isomeric SMILES: CCCCCOC(=O)NC1=NC(=O)N(C=C1F)[C@H]2[C@@H]([C@@H]([C@H](O2)C)O)O
• Recent ClinicalTrials: Serial Measurements of Molecular and Architectural Responses to Therapy (SMMART) PRIME Trial
• Recent EU Clinical Trials: COLLISION RELAPSE trial - Recurrent colorectal liver metastases: repeat local treatment +/- neoadjuvantsystemic therapy - a phase III prospective randomized controlled trial
• Recent NIPH Clinical Trials: ONO-4538-113: A study to evaluate the efficacy and safety of ONO-4538 in combination with ipilimumab and chemotherapy in chemotherapy-naive participants with HER2-negative unresectable advanced or recurrent gastric cancer (including esophagogastric junction cancer)
• Chemical Properties: Structure: Capecitabine is a carbamate ester of cytidine, where the hydrogen at position 5 is replaced by fluorine, and the amino group at position 4 is converted into its N-(penyloxy)carbonyl derivative.; Classification: It is categorized as an antineoplastic agent, prodrug, and antimetabolite. It belongs to the class of carbamate esters, organofluorine compounds, and cytidines.
• Medical Uses: Treatment of Breast Cancer: Widely used orally administered chemotherapeutic drug for metastatic breast cancer.; Colorectal Cancer: Capecitabine, as a prodrug of 5鈥慺luorouracil (5鈥慒U), is utilized to overcome the drawbacks associated with systemic toxicity, lack of effectiveness, selectivity, and resistance often seen with 5鈥慒U-based chemotherapy. It aims to provide a more convenient therapy with improved safety, tolerability, and intratumor drug concentration levels.
• Nanoparticle Delivery Systems: Fluoropyrimidines and Nanoparticles: Fluoropyrimidines like capecitabine are extensively used anticancer drugs globally. Various nanoparticles serve as potential carriers to enhance drug delivery in chemotherapy.; Capecitabine-Loaded Nanoparticles: Studies have explored the use of nanoparticles loaded with capecitabine for the treatment of breast or colorectal cancer.; Co-Delivery Capability: Capecitabine-loaded nanoparticles exhibit co-delivery capabilities with other drugs in a stimuli-responsive manner, making them promising for efficient cancer treatment.

Technology Process of Capecitabine

There total 45 articles about Capecitabine 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: 98.0%

N1-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N4-(pentyloxycarbonyl)cytosine (162204-20-8) → capecitabine (154361-50-9,158798-73-3)

Guidance literature:

N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine; With water; sodium hydroxide; In methanol; at -15 ℃;

With hydrogenchloride; In methanol; water; at -15 ℃; pH=5;

Reference yield: 96.0%

2',3'-bis-O-benzoyl-5'-deoxy-5-fluoro-N4-pentyloxycarbonyl cytidine → capecitabine (154361-50-9,158798-73-3)

Guidance literature:

With sodium hydroxide; In methanol; water; for 2h; Inert atmosphere;

Reference yield: 89.4%

2'3'-O-isopropylidene-5'-deoxy-5-fluoro-N4-(pentyloxycarbonyl)cytidine → capecitabine (154361-50-9,158798-73-3)

Guidance literature:

With trifluoroacetic acid; In methanol; dichloromethane; water; at 10 - 20 ℃; for 3h; Solvent;

upstream raw materials:

N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine

pentyl chloroformate

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose

Downstream raw materials:

5'-deoxy-5-fluorocytidine

Refernces

• 1、 Miranda, Leandro S. De M.,De Souza, Rodrigo O. M. A.,Lea?, Raquel A. C.,Carneiro, Paula F.,Pedraza, Sergio F.,De Carvalho, Otavio V.,De Souza, Stefania P.,Neves, Rebeca V.. "Continuous-Flow Sequential Schotten-Baumann Carbamoylation and Acetate Hydrolysis in the Synthesis of Capecitabine". . p. 2516 - 2520. Retrieved 2019.
• 2、 -. "Cytidine derivative and method for preparing capecitabine medicines through derivative". Paragraph 0065-0069. . Retrieved 2020/05/14.