| Identification | Back Directory | [Name]
Cepharanthine | [CAS]
481-49-2 | [Synonyms]
NSC-623442
Stephanotis
cepharantin
Stephanolin
CEPHARANTHIN
CEPHARANTHINE
CEPHARANTHINUM
CEPHARANTHINE (RG)
CepharanthineWIDELY
CEPHARANTHINE95%,98%
[methylenebis(oxy)]-
Cepharanthine, >=98%
o-methylcepharanoline
Cepharanthine USP/EP/BP
12-O-Methylcepharanoline
Cepharanthine|||CEPHARANTHINE
Stephania extract Cepharanthine
Oxyacanthan,6',12'-dimethoxy-2,2'-dimethyl-6,7-
6',12'-Dimethoxy-2,2'-dimethyl-6,7-[methylenebis(ox
Cepharanthin, 98%, from Stephania japonica (Thunb.) Miers
6',12'-DIMETHOXY-2,2'-DIMETHYL-6,7-(METHYLENEBIS(OXY)OXYACANTHAN)
Oxyacanthan, 6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))-
OXYACANTHAN,6',12'-DIMETHOXY-2,2'-DIMETHYL-6,7-(METHYLLENEBIS (OXY))-
CEPHARANTHINE: OXYACANTHAN,6'',12''-DIMETHOXY-2,2''-DIMETHY1-6,7-(METHYLLENEBIS (OXY))-,
(15S,31R)-36,54-Dimethoxy-16,32-dimethyl-15,16,17,18,31,32,33,34-octahydro-2,6-dioxa-1(4,5)-[1,3]dioxolo[4,5-g]isoquinolina-3(7,1)-isoquinolina-5(1,3),7(1,4)-dibenzenacyclooctaphane
(15S, 31R) -36,54-dimethoxy-16,32-dimethyl-15,16,17,18,31,32,32,33,34-octahydro-2,6-dioxa-1 (4,5) - [1,3] dioxane [4,5-g] isoquinoline-3 (7,1) - isoquinoline-5 (1,3), 7 (1,4) - dibenzocyclooctane
1H-4,6:16,19-Dietheno-21,25-metheno-12H-[1,3]dioxolo[4,5-g]pyrido[2',3':17,18][1,10]dioxacycloeicosino[2,3,4-ij]isoquinoline, 2,3,13,14,14a,15,26,26a-octahydro-22,30-dimethoxy-1,14-dimethyl-, (14aS,26aR)- | [EINECS(EC#)]
228-085-1 | [Molecular Formula]
C37H38N2O6 | [MDL Number]
MFCD00210482 | [MOL File]
481-49-2.mol | [Molecular Weight]
606.71 |
| Chemical Properties | Back Directory | [Melting point ]
145-155° | [alpha ]
D20 +277° (c = 2 in chloroform) | [Boiling point ]
654.03°C (rough estimate) | [density ]
1.1761 (rough estimate) | [refractive index ]
1.5300 (estimate) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
Soluble in DMSO (35 mg/mL) or ethanol (20 mg/mL) | [form ]
solid | [pka]
7.61±0.20(Predicted) | [color ]
Pale yellow | [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. | [InChIKey]
YVPXVXANRNDGTA-WDYNHAJCSA-N | [SMILES]
C1CC2C=C3OCOC3=C3OC4C(OC)=CC5CCN(C)[C@]([H])(CC6=CC(=C(OC)C=C6)OC6C=CC(C[C@@]([H])(C=23)N1C)=CC=6)C=5C=4 |
| Hazard Information | Back Directory | [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. In this chapter, 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]
antineoplastic, hepatoprotectant, radiopropective | [Definition]
ChEBI: A bisbenzylisoquinoline alkaloid from tubers of Stephania; stimulates recovery of immunologic function in lymphatic system after administration of antineoplastic agents or x-irradiation. | [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 alopecia
Inhibit various types of cancerous tumor growth
Prevent cancer metastasis
Stimulate white blood cell production
Induce apoptosis (cell death) and autophagy in cancerous cells
Restore the effectiveness of anticancer drugs for resistant tumors
Boost the effectiveness of certain chemotherapies
Inhibit the replication of HIV-1 virus
Inhibit different types of Coronavirus
Provide relief of allergies by inhibiting the release of histamine
Possess anti-viral and anti-inflammatory effects
Scavenge 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. | [storage]
Store at -20°C | [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 |
|
|