Cepharanthine

Chemical compound

none

Identifiers

IUPAC name

(14S,27R)-22,33-dimethoxy-13,28-dimethyl-2,5,7,20-tetraoxa-13,28-diazaoctacyclo[25.6.2.2^16,19.1^3,10.1^21,25.0^4,8.0^31,35.0^14,39]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 InfoCard100.208.632

Chemical and physical dataFormulaC₃₇H₃₈N₂O₆Molar mass606.719 g·mol⁻¹3D 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 HTLV in lab research. ^[2] 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. ^[3]

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): 235–46. doi:10.1007/s10753-013-9734-8. PMID 24045962. S2CID 7186762.
^ Toyama M, Hamasaki T, Uto T, Aoyama H, Okamoto M, Hashmoto Y, Baba M (July 2012). "Synergistic inhibition of HTLV-1-infected cell proliferation by combination of cepharanthine and a tetramethylnaphthalene derivative". Anticancer Research. 32 (7): 2639–45. PMID 22753721.
^ Rogosnitzky M, Danks R (2011). "Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions" (PDF). Pharmacological Reports. 63 (2): 337–47. doi:10.1016/S1734-1140(11)70500-X. PMID 21602589.

Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)

pyrazolones /
pyrazolidines

salicylates

acetic acid derivatives
and related substances

oxicams

propionic acid
derivatives (profens)

Alminoprofen
Benoxaprofen^†
Carprofen^‡
Dexibuprofen
Dexketoprofen
Fenbufen
Fenoprofen
Flunoxaprofen
Flurbiprofen
Ibuprofen^#
Ibuproxam
Indoprofen^†
Ketoprofen
Loxoprofen
Miroprofen
Naproxen
Oxaprozin
Pelubiprofen
Piketoprofen
Pirprofen
Suprofen
Tarenflurbil
Tepoxalin^‡
Tiaprofenic acid
Vedaprofen^‡
Zaltoprofen
COX-inhibiting nitric oxide donator: Naproxcinod

n-arylanthranilic
acids (fenamates)

COX-2 inhibitors
(coxibs)

other

NSAID
combinations

Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.