Cepharanthine

Base Information

• Chemical Name: Cepharanthine
• CAS No.: 481-49-2
• Molecular Formula: C₃₇H₃₈N₂O₆
• Molecular Weight: 606.719
• European Community (EC) Number: 683-114-9
• NSC Number: 758965
• UNII: 7592YJ0J6T
• DSSTox Substance ID: DTXSID6045957
• Nikkaji Number: J5.779G
• Wikipedia: Cepharanthine
• Wikidata: Q15410888
• NCI Thesaurus Code: C83611
• Pharos Ligand ID: APJ9F7STHYFZ
• Metabolomics Workbench ID: 67589
• ChEMBL ID: CHEMBL449782
• Mol file: 481-49-2.mol

Synonyms:6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthan;cepharanthin;cepharanthine

Chemical Property of Cepharanthine

Chemical Property:

• Appearance/Colour: Yellow powder.
• Melting Point: 140 - 145oC
• Refractive Index: 1.608
• Boiling Point: 654.03°C (rough estimate)
• PKA: 7.61±0.20(Predicted)
• PSA: 61.86000
• Density: 1.227 g/cm³
• LogP: 6.74970
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Soluble in DMSO (35 mg/mL) or ethanol (20 mg/mL)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 606.27298694
• Heavy Atom Count: 45
• Complexity: 994

Purity/Quality:

99% ^*data from raw suppliers

Cepharanthine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C4=C2C1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)CC7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)C[C@@H]7C8=CC(=C(C=C8CCN7C)OC)O4)OC)OCO3
• Recent ClinicalTrials: Study of Oral High/Low-dose Cepharanthine Compared With Placebo in Non Hospitalized Adults With COVID-19
• Recent NIPH Clinical Trials: Cepharanthine trial
• Description: Cepharanthine is diclofenac quinoline alkaloid isolated from rhizome of Stephania japonica, which was first recorded in “Bencao shiyi” and functions as clearing heat, promoting diuresis and detumescence in traditional Chinese medicine. Cepharanthine is a pure and natural extract of the Stephania cepharantha Hayata plant, a rare species that is native to Kotosho Island, southeast of Taiwan. In 1914, the renowned botanist, Bunzo Hayata reported the plant for the first time. Two decades later, Dr. Heisaburo Kondo purified its active ingredient and named it “Cepharanthine.” Stephania japonica was used to treat tuberculosis and other consumptive diseases which provided a clue for its development on lung disease.
• Physical properties: Appearance: light yellow or yellow powder. Solubility: soluble in acidic aqueous solution and ether, acetone, and other organic solvents; insoluble in petroleum ether. Melting point: 148–150?°C. Specific optical rotation: +277°.
• Uses: Cepharanthine is a biscoclaurine alkaloid that has antiinflammatory, antineoplastic, hepatoprotectant, radiopropective and other biological functions. It is used to treat many acute and chronic diseases, including pit viper bites, alopecia areata, and leucopenia in radiation therapy.
• Clinical Use: The major clinical application of cepharanthine is to improve their immunity impaired by chemotherapy or radiotherapy in tumor patients. In addition, cepharanthine can increase the sensitivity to antitumor drugs, and itself also has a certain antitumor effect. Now, it is commonly used as adjuvant drug for anticancer treatment.

Technology Process of Cepharanthine

There total 4 articles about Cepharanthine 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:

cepharanthine-2-N-oxide → cepharanthine (481-49-2)

Guidance literature:

With hydrogenchloride; zinc; In water; at 20 ℃; for 2h;

DOI:10.1021/np400084t

Reference yield:

cepharanthine-2′α-N-oxide (1431330-90-3) → cepharanthine (481-49-2)

Guidance literature:

With hydrogenchloride; zinc; In water; at 20 ℃; for 2h;

DOI:10.1021/np400084t

Reference yield:

2-{7-[4-(2-amino-ethyl)-2-methoxy-phenoxy]-benzo[1,3]dioxol-5-yl}-ethylamine → cepharanthine (481-49-2)

Guidance literature:

Reaktion ueber mehrere Stufen;

DOI:10.1016/S0040-4039(00)90667-1

upstream raw materials:

cepharanthine-2′α-N-oxide

Downstream raw materials:

(R)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

dihydrosecocepharanthine

secocepharanthine

Refernces

• 1、 -. "Compounds and compositions for treating infection". . . Retrieved 2009/04/24.