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 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.

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[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): 235–46. doi:10.1007/s10753-013-9734-8. PMID 24045962. S2CID 7186762.

[2] 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.

[3] 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.

[1]

[2]

[3]

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone^‡
salicylates	Aspirin (acetylsalicylic acid)^# Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac^†
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
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)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine^† Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib^‡ Deracoxib^‡ Etoricoxib Firocoxib^‡ Lumiracoxib^† Mavacoxib^‡ Parecoxib Robenacoxib^‡ Rofecoxib^† Valdecoxib^†
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.
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