Cepharanthine
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MedKoo CAT#: 205876

CAS#: 481-49-2

Description: Cepharanthine (CEP) is a biscoclaurine alkaloid isolated from Stephania cepharantha. It has anticancer, antiinflammatory, antiallergic, immunomo- dulatory, and many other interesting biological activities. Cepharanthine has been widely used in Japan for more than 40 years to treat a wide variety of acute and chronic diseases. CEP inhibits tumor necrosis factor (TNF)-α-mediated NFκB stimulation, plasma membrane lipid peroxidation and platelet aggregation and suppresses cytokine production. It has also been shown to scavenge free radicals and to have a protective effect against some of the responses mediated by pro-inflammatory cytokines such as TNF-α, interleukin (IL)-1β and IL6. CEP has successfully been used to treat a diverse range of medical conditions, including radiation-induced leukopenia, idiopathic thrombocytopenic purpura, alopecia areata, alopecia pityrodes, venomous snakebites, xerostomia, sarcoidosis, refractory anemia and various cancer-related conditions. No safety issues have been observed with CEP, and side effects are very rarely reported.


Chemical Structure

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Cepharanthine
CAS# 481-49-2

Theoretical Analysis

MedKoo Cat#: 205876
Name: Cepharanthine
CAS#: 481-49-2
Chemical Formula: C37H38N2O6
Exact Mass: 606.27299
Molecular Weight: 606.71
Elemental Analysis: C, 73.25; H, 6.31; N, 4.62; O, 15.82

Price and Availability

Size Price Availability Quantity
25.0mg USD 150.0 Same day
50.0mg USD 250.0 Same day
100.0mg USD 450.0 Same day
200.0mg USD 550.0 Same day
500.0mg USD 650.0 Same day
1.0g USD 750.0 Same day
2.0g USD 1250.0 Same day
5.0g USD 1750.0 Same day
10.0g USD 3050.0 2 Weeks
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Synonym: Cepharanthine; 6',12'-Dimethoxy-2,2'-dimethyl-6,7-[methylenebis- (oxy)]oxyacanthan; Cepharanthin; O-Methylcepharanoline.

IUPAC/Chemical Name: (15S,31R)-36,53-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-5,7(1,4)-dibenzenacyclooctaphane

InChi Key: RCBDVSWQYYTNLG-WDYNHAJCSA-N

InChi Code: InChI=1S/C37H38N2O6/c1-38-13-11-24-18-32(41-4)33-20-27(24)28(38)16-23-7-10-30(31(17-23)40-3)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/t28-,29+/m1/s1

SMILES Code: COC1=CC2=C3C=C1OC4=C(OCO5)C5=CC6=C4[C@@](CC7=CC=C(OC(C(OC)=C8)=CC=C8C[C@@]3([H])N(C)CC2)C=C7)([H])N(C)CC6

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 606.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Fang ZH, Li YJ, Chen Z, Wang JJ, Zhu LH. Inhibition of signal transducer and activator of transcription 3 and cyclooxygenase-2 is involved in radiosensitization of cepharanthine in HeLa cells. Int J Gynecol Cancer. 2013 May;23(4):608-14. doi: 10.1097/IGC.0b013e31828a05fd. PubMed PMID: 23466568.

2: Harada T, Harada K, Ueyama Y. The enhancement of tumor radioresponse by combined treatment with cepharanthine is accompanied by the inhibition of DNA damage repair and the induction of apoptosis in oral squamous cell carcinoma. Int J Oncol. 2012 Aug;41(2):565-72. doi: 10.3892/ijo.2012.1501. Epub 2012 May 31. PubMed PMID: 22664937.

3: Tabata R, Tabata C, Tazoh A, Nagai T. Low dose cepharanthine ameliorates immune thrombocytopenic purpura associated with multiple myeloma. Int Immunopharmacol. 2012 Jul;13(3):242-4. doi: 10.1016/j.intimp.2012.04.015. Epub 2012 May 3. Review. PubMed PMID: 22561120.

4: Uthaisar K, Seubwai W, Srikoon P, Vaeteewoottacharn K, Sawanyawisuth K, Okada S, Wongkham S. Cepharanthine suppresses metastatic potential of human cholangiocarcinoma cell lines. Asian Pac J Cancer Prev. 2012;13 Suppl:149-54. PubMed PMID: 23480757.

5: Li H, Yan Z, Ning W, Xiao-Juan G, Cai-Hong Z, Jin-Hua J, Fang M, Qing-Duan W. Using rhodamine 123 accumulation in CD8 cells as a surrogate indicator to study the P-glycoprotein modulating effect of cepharanthine hydrochloride in vivo. J Biomed Biotechnol. 2011;2011:281651. doi: 10.1155/2011/281651. Epub 2011 Jun 30. PubMed PMID: 21765632; PubMed Central PMCID: PMC3134191.

6: Rogosnitzky M, Danks R. Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions. Pharmacol Rep. 2011;63(2):337-47. Review. PubMed PMID: 21602589.

7: Seubwai W, Vaeteewoottacharn K, Hiyoshi M, Suzu S, Puapairoj A, Wongkham C, Okada S, Wongkham S. Cepharanthine exerts antitumor activity on cholangiocarcinoma by inhibiting NF-kappaB. Cancer Sci. 2010 Jul;101(7):1590-5. doi: 10.1111/j.1349-7006.2010.01572.x. Epub 2010 Mar 24. PubMed PMID: 20412118.

8: Harada K, Ferdous T, Itashiki Y, Takii M, Mano T, Mori Y, Ueyama Y. Cepharanthine inhibits angiogenesis and tumorigenicity of human oral squamous cell carcinoma cells by suppressing expression of vascular endothelial growth factor and interleukin-8. Int J Oncol. 2009 Nov;35(5):1025-35. PubMed PMID: 19787256.

9: Takahashi-Makise N, Suzu S, Hiyoshi M, Ohsugi T, Katano H, Umezawa K, Okada S. Biscoclaurine alkaloid cepharanthine inhibits the growth of primary effusion lymphoma in vitro and in vivo and induces apoptosis via suppression of the NF-kappaB pathway. Int J Cancer. 2009 Sep 15;125(6):1464-72. doi: 10.1002/ijc.24521. PubMed PMID: 19521981.

10: Harada K, Ferdous T, Itashiki Y, Takii M, Mano T, Mori Y, Ueyama Y. Effects of cepharanthine alone and in combination with fluoropyrimidine anticancer agent, S-1, on tumor growth of human oral squamous cell carcinoma xenografts in nude mice. Anticancer Res. 2009 Apr;29(4):1263-70. PubMed PMID: 19414373.   



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