Details of the Drug

General Information of Drug (ID: DM9Y5JB)

Drug Name
Cepharanthine
Synonyms
CEPHARANTHINE; Cepharanthin; (+)-Cepharanthine; O-Methylcepharanoline; Cepharantin; Cepharanthine [JAN]; UNII-7592YJ0J6T; CCRIS 6539; NSC 623442; BRN 0075231; 6',12'-Dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))oxyacanthan; CHEBI:3546; 7592YJ0J6T; NSC623442; Cepharanthine (JAN); NSC-623442; ecaene (non-preferred name); DSSTox_RID_81253; DSSTox_CID_25957; DSSTox_GSID_45957; Oxyacanthan, 6',12'-dimethoxy-2,2'-dimethyl-6,7-(methylenebis(oxy))-; CAS-481-49-2; SR-01000779734; Cepharanthin,(S)
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski):
1		 Molecular Weight 606.7
Logarithm of the Partition Coefficient Not Available
Rotatable Bond Count 2
Hydrogen Bond Donor Count 0
Hydrogen Bond Acceptor Count 8
Chemical Identifiers
Formula
C37H38N2O6
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
Canonical SMILES
CN1CCC2=CC3=C(C4=C2C1CC5=CC=C(C=C5)OC6=C(C=CC(=C6)CC7C8=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
InChIKey
YVPXVXANRNDGTA-WDYNHAJCSA-N
Cross-matching ID
PubChem CID
10206
ChEBI ID
CHEBI:3546
CAS Number
481-49-2
VARIDT ID
DR01503

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ATP-dependent translocase ABCB1 (ABCB1) OTEJROBO MDR1_HUMAN Gene/Protein Processing [2]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [3]
Induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1) OT2YYI1A MCL1_HUMAN Gene/Protein Processing [3]
Poly polymerase 1 (PARP1) OT310QSG PARP1_HUMAN Gene/Protein Processing [3]
Potassium voltage-gated channel subfamily H member 2 (KCNH2) OTZX881H KCNH2_HUMAN Gene/Protein Processing [4]
Serine/threonine-protein kinase mTOR (MTOR) OTHH8KU7 MTOR_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Cepharanthin, a multidrug resistant modifier, is a substrate for P-glycoprotein. J Pharmacol Exp Ther. 1995 Oct;275(1):73-8.
2 Cepharanthine potently enhances the sensitivity of anticancer agents in K562 cells. Cancer Sci. 2005 Jun;96(6):372-6. doi: 10.1111/j.1349-7006.2005.00057.x.
3 Tetrandrine and cepharanthine induce apoptosis through caspase cascade regulation, cell cycle arrest, MAPK activation and PI3K/Akt/mTOR signal modification in glucocorticoid resistant human leukemia Jurkat T cells. Chem Biol Interact. 2019 Sep 1;310:108726. doi: 10.1016/j.cbi.2019.108726. Epub 2019 Jun 28.
4 Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.