481-49-2

Basic information

• Product Name: Cepharanthine
• Synonyms: 6',12'-DIMETHOXY-2,2'-DIMETHYL-6,7-(METHYLENEBIS(OXY)OXYACANTHAN);CEPHARANTHIN;CEPHARANTHINE;OXYACANTHAN,6',12'-DIMETHOXY-2,2'-DIMETHYL-6,7-(METHYLLENEBIS (OXY))-;cepharantin;o-methylcepharanoline;CEPHARANTHINE95%,98%;Stephanotis
• CAS NO: 481-49-2
• Molecular Formula: C₃₇H₃₈N₂O₆
• Molecular Weight: 606.71
• Product Categories: Alkaloids;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Other APIs;Inhibitors
• Mol File: 481-49-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 145-155°
• Boiling Point: 654.03°C (rough estimate)
• Appearance: /
• Density: 1.1761 (rough estimate)
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Soluble in DMSO (35 mg/mL) or ethanol (20 mg/mL)
• PKA: 7.61±0.20(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: Cepharanthine(CAS DataBase Reference)
• NIST Chemistry Reference: Cepharanthine(481-49-2)
• EPA Substance Registry System: Cepharanthine(481-49-2)

Safety Data

• Hazardous Substances Data: 481-49-2(Hazardous Substances Data)

Usage

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°.

History

Promoting leukocytosis of cepharanthine in tuberculosis patients was first recorded in the proceeding Institute of Chemotherapy by the Japanese scholar Yamaguchi in 1946. In 1948, Chinese scholar Yuhuang Zhao also received this compound and published it in D.M.?Med.It is thought that cepharanthine may stimulate the reticuloendothelial system, then activate hematopoietic tissue, and promote myeloproliferation. Therefore, the number of white blood cells in the peripheral blood increased significantly. Due to its good safety, cepharanthine is currently widely used in cancer patients with granulocytopenia or leukopenia embolism after radiotherapy and chemotherapy and so on.In addition, Chinese scientists extracted five kinds of dibenzylisoquinoline alkaloids from Chinese herbal medicine in 1977, which could significantly improve the silicosis symptoms in rat . In 1993, it was issued as anti-pneumoconiosis drug by CFDA and is used for delaying the progress of pneumoconiosis in clinic.

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.

Definition

ChEBI: Cepharanthine is a bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. It is a member of isoquinolines and a bisbenzylisoquinoline alkaloid.

benefits

When Cepharanthine is absorbed into the body, it acts through multiple biochemical and pharmacological mechanisms and generates a tremendous amount of beneficial effects on one's health. Regrow hair in a number of patients with different types of alopeciaInhibit various types of cancerous tumor growthPrevent cancer metastasisStimulate white blood cell productionInduce apoptosis (cell death) and autophagy in cancerous cellsRestore the effectiveness of anticancer drugs for resistant tumorsBoost the effectiveness of certain chemotherapies Inhibit the replication of HIV-1 virusInhibit different types of CoronavirusProvide relief of allergies by inhibiting the release of histaminePossess anti-viral and anti-inflammatory effectsScavenge free radicals and prevent oxidation

Biological Activity

Cepharanthine, a biscoclaurine alkaloid isolated from a Chinese folklore plant Stephania cepharantha, inhibited HIV-1 replication by inhibiting kappa B, a potent inducer of HIV-1 gene expression and displayed potent activity against SARS coronavirus, HSV-1, and coxsackie B3 along with antitumor and immunomodulating activity. As cepharanthine had strong activity against both RNA and DNA viruses it may be a source of potential lead compounds for developing new antivirals.

Pharmacology

The pharmacological effects of cepharanthine are very broad, mainly for the promotion of leukocytosis, antitumor, anti-inflammation, improvement of the body immunity, and other aspects of efficacy. Improvement of leukocytosis is the most widely studied among them, and the mechanism may be to stimulate the reticular endothelium system, activate hematopoietic tissue, and promote bone marrow hyperplasia .Cepharanthine is also a good antitumor drug sensitizer. It can significantly improve their efficacy and reduce their side effects when combined with other antitumor drugs, as manifested by increasing the concentration of FT-207 metabolite (5-Fu) in tumor tissue under cepharanthine and FT-207 combination therapy, which was significantly higher than that in blood , suggesting that cepharanthine has the potential to improve the efficacy of antitumor drugs.

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.

Side effects

Cepharanthine is an extraordinary medicine from Japan, where it has been widely used for the past seventy years to treat a variety of acute and chronic diseases, with little known side-effects. Common side effects are reported as below. loss of appetite, disc omfort in stomach, rash/eruption, itch , nausea, diarrhea, headache, dizziness, swelling in face/hands/feet, irregular menstruation, etc.

References

Rogosnitzky and Dank (2011), Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions; Pharmacol. Rep., 63 337 Huang et al. (2014), Cepharanthine, an alkaloid from Stephania cepharantha Hayata inhibits the inflammatory response in the RAW264.7 cell and mouse models; Inflammation, 37 235 Wang et al. (2020), Cepharanthine hydrochloride induces mitophagy targeting GPR30 in hepatocellular carcinoma (HCC); Expert Opin. Ther. Targets, 24 389 Zhang et al. (2019), Downregulation of MYO1C mediated by cepharanthine inhibits autophagosome-lysosome fusion through blockade of the F-actin network; J. Exp. Clin. Cancer Res. 38 457 Rosognitzky et al. (2020), Cepharanthine: a review of the antiviral potential of a Japanese-approved alopecia drug in COVID-19; Pharmacol. Rep., 72 1509

InChI:InChI=1/C37H38N2O6/c1-38-13-11-24-18-31(41-4)33-20-27(24)28(38)16-23-7-10-30(40-3)32(17-23)44-26-8-5-22(6-9-26)15-29-35-25(12-14-39(29)2)19-34-36(37(35)45-33)43-21-42-34/h5-10,17-20,28-29H,11-16,21H2,1-4H3

Upstream product

• 1431330-90-3 cepharanthine-2′α-N-oxide 

Downstream Products

• 89503-78-6 secocepharanthine 
• 89503-79-7 dihydrosecocepharanthine 
• 19879-50-6 (R)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol 

Relevant articles and documents

Cytotoxic bisbenzylisoquinoline alkaloids from Stephania epigaea

Six new bisbenzylisoquinoline alkaloids (1-6) and seven known compounds (8-14) were isolated from the tubers of Stephania epigaea, in addition to the major alkaloid, cepharanthine (7). The structures of 1-6 were elucidated by combined spectroscopic data analysis and chemical methods, with their configurations determined from their optical rotation values and confirmed using circular dichroism. Compounds 1-6 belong to the oxyacanthine type of bisbenzylisoquinoline alkaloids and have a rare methylenedioxy substituent. Compound 1, a dimer composed of benzylisoquinoline and seco-aristolactam units, represents a new type of bisbenzylisoquinoline alkaloid, while compounds 3-6 are bisbenzylisoquinoline N-oxides. These compounds were evaluated for their in vitro cytotoxicities against six human cancer cell lines (A-549, ECA109, HL-60, MCF-7, SMMC-7721, and SW480). Cepharanthine (7), the major component of S. epigaea, exhibited cytotoxicity against all of these cancer cell lines except ECA109, while its known analogue, 10, displayed cytotoxicity against all six cancer cell lines.