Cepharanthine

Cepharanthine
Clinical data
Other names	Cepharantin, O-Methylcepharanoline
AHFS/Drugs.com	International Drug Names
ATC code	none;
Identifiers
	IUPAC name (14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.216,19.13,10.121,25.04,8.031,35.014,39]nonatriaconta-1(33),3(39),4(8),9,16(38),17,19(37),21,23,25(36),31,34-dodecaene;
CAS Number	481-49-2;
PubChem CID	10206;
ChemSpider	9791;
UNII	7592YJ0J6T;
ChEMBL	ChEMBL449782;
CompTox Dashboard (EPA)	DTXSID6045957 ;
ECHA InfoCard	100.208.632
Chemical and physical data
Formula	C37H38N2O6
Molar mass	606.719 g·mol−1
3D model (JSmol)	Interactive image;
	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;
	InChI InChI=1S/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/t28-,29+/m1/s1; Key:YVPXVXANRNDGTA-WDYNHAJCSA-N;

Cepharanthine is an antiinflammatory and antineoplastic compound isolated from Stephania.¹ Due to these modalities, it has been shown effective against viral infections such as HTLV and hantavirus in early stage research.²³ Additionally, it 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. ⁴

References

Huang H, Hu G, Wang C, Xu H, Chen X, Qian A (February 2014). "Cepharanthine, an alkaloid from Stephania cepharantha Hayata, inhibits the inflammatory response in the RAW264.7 cell and mouse models". Inflammation. 37 (1): 235–246. doi:10.1007/s10753-013-9734-8. PMID 24045962. S2CID 7186762.
Toyama M, Hamasaki T, Uto T, Aoyama H, Okamoto M, Hashmoto Y, et al. (July 2012). "Synergistic inhibition of HTLV-1-infected cell proliferation by combination of cepharanthine and a tetramethylnaphthalene derivative". Anticancer Research. 32 (7): 2639–2645. PMID 22753721.
Wen X, Zhang L, Liu Q, Xiao X, Huang W, Wang Y (August 2022). "Screening and identification of HTNV_pv entry inhibitors with high-throughput pseudovirus-based chemiluminescence". Virologica Sinica. 37 (4): 531–537. doi:10.1016/j.virs.2022.04.015. PMC 9437608. PMID 35513270.
Rogosnitzky M, Danks R (2011). "Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions". Pharmacological Reports. 63 (2): 337–347. doi:10.1016/S1734-1140(11)70500-X. PMID 21602589.

[1] Huang H, Hu G, Wang C, Xu H, Chen X, Qian A (February 2014). "Cepharanthine, an alkaloid from Stephania cepharantha Hayata, inhibits the inflammatory response in the RAW264.7 cell and mouse models". Inflammation. 37 (1): 235–246. doi:10.1007/s10753-013-9734-8. PMID 24045962. S2CID 7186762.

[2] Toyama M, Hamasaki T, Uto T, Aoyama H, Okamoto M, Hashmoto Y, et al. (July 2012). "Synergistic inhibition of HTLV-1-infected cell proliferation by combination of cepharanthine and a tetramethylnaphthalene derivative". Anticancer Research. 32 (7): 2639–2645. PMID 22753721.

[3] Wen X, Zhang L, Liu Q, Xiao X, Huang W, Wang Y (August 2022). "Screening and identification of HTNV_pv entry inhibitors with high-throughput pseudovirus-based chemiluminescence". Virologica Sinica. 37 (4): 531–537. doi:10.1016/j.virs.2022.04.015. PMC 9437608. PMID 35513270.

[4] Rogosnitzky M, Danks R (2011). "Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions". Pharmacological Reports. 63 (2): 337–347. doi:10.1016/S1734-1140(11)70500-X. PMID 21602589.

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