Cepharanthine | CAS#481-49-2 | MedKoo Biosciences

MedKoo Cat#: 205876 | Name: Cepharanthine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Cepharanthine

CAS#481-49-2

Theoretical Analysis

MedKoo Cat#: 205876

Name: Cepharanthine

CAS#: 481-49-2

Chemical Formula: C37H38N2O6

Exact Mass: 606.2730

Molecular Weight: 606.71

Elemental Analysis: C, 73.25; H, 6.31; N, 4.62; O, 15.82

Price and Availability

Size	Price	Availability
25mg	USD 150.00	Ready to ship
50mg	USD 225.00	Ready to ship
100mg	USD 350.00	Ready to ship
200mg	USD 500.00	Ready to ship
500mg	USD 650.00	Ready to ship
1g	USD 750.00	Ready to ship
2g	USD 1,050.00	Ready to ship
5g	USD 1,750.00	Ready to ship
10g	USD 2,850.00	2 weeks

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Related CAS #

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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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#AK30315

QC Data

View QC data: current batch, Lot#AK30315

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Cepharanthine is an alkaloid derived from Stephania cepharantha Hayata that possesses anti-inflammatory and antioxidative activities.

In vitro activity:

To further investigated the influence of CEP in vitro, BV-2 microglia cells were induced by oxygen and glucose deprivation/reoxygenation (OGD/R) and treated with different concentrations of CEP (0.25, 0.5, 1, 2.5 μg/mL) or 10 μM Z-YVADFMK. Immunofluorescence for NLRP3 showed that NLRP3 expression were significantly increased by OGD/R induction, and dosedependently reduced by CEP in BV-2 cells following OGD/R (Fig. 6A). The expression of NLRP3, ASC and caspase-1, known as NLRP3-inflammasome components, was detected by western blot (Fig. 6B-D). The protein expression levels of NLRP3, ASC and cleaved caspsase-1 were up-regulated in OGD/R-induced cells, while down-regulated by CEP treatment in a dose-dependent manner. No difference was found in the expression of full length caspase-1 among different groups. ELISA analysis revealed an elevation in the release of IL-1β and IL-18 mediated by NLRP3 inflammasome following OGD/R, which were suppressed by CEP treatment (Fig. 6E-F). The inhibition of CEP on inflammatory cytokine production was in comparable with treatment with Z-YVAD-FMK, a caspase inhibitor. These results indicated that CEP inhibited NLRP3 inflammasome-mediated inflammation in OGD/R-treated BV-2 cells. Reference: Biomed Pharmacother. 2020 Jul;127:110151. https://pubmed.ncbi.nlm.nih.gov/32559840/

In vivo activity:

To study the effect of CEP on NLRP3-inflammasome, NLRP3-inflammasome components including NLRP3, ASC and caspase-1, as well as subsequent IL-1β and IL-18 release were evaluated. Immunofluorescence staining for NLRP3 and Iba1-labled microglia was performed in the brain following tMCAO (Fig. 3A). Quantification showed that total Iba1-positive microglia and total NLRP3-pisitive cells were elevated in MCAO mice, while lowered by CEP treatment at a dose-dependent manner (Fig. 3B-C). Moreover, staining revealed that increased NLRP3 and Iba1 immunoreactivity in tMCAO mice were inhibited by CEP treatment. Western blotting analysis of NLRP3-inflammasome components showed that the expression levels of NLRP3, ASC and cleaved-caspase-1 were increased after tMCAO, while decreased in the presence of CEP (Fig. 4A-C). There was no difference in the expression of the fulllength caspase-1 among different groups. NLRP3 inflammasome-induced subsequent release of inflammatory cytokines including IL1β and IL-18 was both down-regulated by CEP treatment in tMCAO mice (Fig. 4D-E). These results demonstrated that CEP contributed to suppression of NLRP3 inflammasome-induced inflammation following tMCAO. Reference: Biomed Pharmacother. 2020 Jul;127:110151. https://pubmed.ncbi.nlm.nih.gov/32559840/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	68.3	112.63

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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

Formulation protocol:

1. Zhao J, Piao X, Wu Y, Liang S, Han F, Liang Q, Shao S, Zhao D. Cepharanthine attenuates cerebral ischemia/reperfusion injury by reducing NLRP3 inflammasome-induced inflammation and oxidative stress via inhibiting 12/15-LOX signaling. Biomed Pharmacother. 2020 Jul;127:110151. doi: 10.1016/j.biopha.2020.110151. Epub 2020 May 19. PMID: 32559840. 2. Wu Y, Cao Y, Wang S, Xu X, Wang M. Cepharanthine promotes the effect of dexmedetomidine on the deposition of β-amyloid in the old age of the senile dementia rat model by regulating inflammasome expression. Folia Neuropathol. 2019;57(4):348-356. doi: 10.5114/fn.2019.89855. PMID: 32337948. 3. Zhao J, Piao X, Wu Y, Liang S, Han F, Liang Q, Shao S, Zhao D. Cepharanthine attenuates cerebral ischemia/reperfusion injury by reducing NLRP3 inflammasome-induced inflammation and oxidative stress via inhibiting 12/15-LOX signaling. Biomed Pharmacother. 2020 Jul;127:110151. doi: 10.1016/j.biopha.2020.110151. Epub 2020 May 19. PMID: 32559840. 4. Cierluk K, Szlasa W, Rossowska J, Tarek M, Szewczyk A, Saczko J, Kulbacka J. Cepharanthine induces ROS stress in glioma and neuronal cells via modulation of VDAC permeability. Saudi Pharm J. 2020 Nov;28(11):1364-1373. doi: 10.1016/j.jsps.2020.08.026. Epub 2020 Sep 4. PMID: 33250643; PMCID: PMC7679435.

In vitro protocol:

In vivo protocol:

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.