Drug Information

General Information
Drug ID
DR00162
Drug Name
Etoposide
Synonyms
(-)-Etoposide; 4'-Demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside; 4'-Demethylepipodophyllotoxin 9-(4,6-O-(R)-ethylidene-beta-D-glucopyranoside); 4'-Demethylepipodophyllotoxin 9-(4,6-O-ethylidene-beta-D-glucopyranoside); 4'-Demethylepipodophyllotoxin ethylidene-.beta.-D-glucoside; 4'-O-Demethyl-1-O-(4,6-O-ethylidene-beta-D-glucopyranosyl)epipodophyllotoxin; 4-Demethylepipodophyllotoxin beta-D-ethylideneglucoside; 4-Demethylepipodophyllotoxin-.beta.-D-ethylideneglucoside; DEMETHY-EPIPODOPHYLLOTOXIN, ETHYLIDENE GLUCOSIDE; Demethyl EpipodophyllotoxinEthylidine Glucoside; Demethyl-epiodophyllotoxin ethylidene glucoside; Demethylepipodophyllotoxin-beta-D-ethylideneglucoside; E0675; Epipodophyllotoxin VP-16213; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-.beta.-D-glucopyranoside; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside; Epipodophyllotoxin, 4'-demethyl-, 4,6-O-ethylidene-beta-D-glucopyranoside (8CI); Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-.beta.-D-glucopyranoside); Epipodophyllotoxin, 4'-demethyl-, 9-(4,6-O-ethylidene-beta-D-glucopyranoside); Eposide; Eposin; Eposin (TN); Eposin, Vepesid, VP-16, Toposar, Etoposide; Etopol; Etopophos (TN); Etopophos (phosphate salt);Etoposide (VP16); Etoposide (JP15/USP/INN); Etoposide [USAN:INN:BAN:JAN]; Etoposido; Etoposido [INN-Spanish]; Etoposidum; Etoposidum [INN-Latin]; Etosid; Lastet; NK 171; Toposar; Trans-Etoposide; VP 16; VP 16 (pharmaceutical); VP 16-213; VP 16213; VP-16; VP-16 (TN); VP-16-213; VePESID (TN); VePesid; Vepesid J; Vepeside; Zuyeyidal
Drug Type
Small molecular drug
Indication Testicular cancer [ICD11:2C80] Approved [1]
Kaposi's sarcoma [ICD11:2B57] Approved [1]
Ewing's sarcoma [ICD11:2B52] Approved [1]
Lung cancer [ICD11:2C25] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
Formula
C29H32O13
Canonical SMILES
CC1OCC2C(O1)C(C(C(O2)OC3C4COC(=O)C4C(C5=CC6=C(C=C35)OCO6)C7=CC(=C(C(=C7)OC)O)OC)O)O
InChI
InChI=1S/C29H32O13/c1-11-36-9-20-27(40-11)24(31)25(32)29(41-20)42-26-14-7-17-16(38-10-39-17)6-13(14)21(22-15(26)8-37-28(22)33)12-4-18(34-2)23(30)19(5-12)35-3/h4-7,11,15,20-22,24-27,29-32H,8-10H2,1-3H3/t11-,15+,20-,21-,22+,24-,25-,26-,27-,29+/m1/s1
InChIKey
VJJPUSNTGOMMGY-MRVIYFEKSA-N
CAS Number
CAS 33419-42-0
Pharmaceutical Properties Molecular Weight 588.6 Topological Polar Surface Area 161
Heavy Atom Count 42 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 13
XLogP
0.6
PubChem CID
36462
PubChem SID
104019076 ,104234176 ,104324084 ,11110521 ,117664408 ,117682510 ,119525100 ,12013288 ,121363248 ,124349593 ,124659141 ,124757097 ,124800231 ,124893613 ,125163901 ,127298729 ,127298730 ,127298731 ,127298732 ,14886949 ,14935915 ,24278178 ,24769897 ,34677904 ,46386954 ,46500626 ,46505434 ,4733 ,47362874 ,48182835 ,48332078 ,49681767 ,49699016 ,49855364 ,53787668 ,56463308 ,57311878 ,597749 ,71825014 ,75974183 ,7847193 ,7979208 ,8145856 ,8174504 ,85148351 ,85788790 ,89850276 ,92308660 ,92308790 ,99437037
ChEBI ID
ChEBI:4911
TTD Drug ID
D0B7EB
DT(s) Transporting This Drug ABCG1 Transporter Info ATP-binding cassette sub-family G member 1 Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [3]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [4]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [5]
MRP3 Transporter Info Multidrug resistance-associated protein 3 Substrate [6]
OATP1B1 Transporter Info Organic anion transporting polypeptide 1B1 Substrate [7]
OATP1B3 Transporter Info Organic anion transporting polypeptide 1B3 Substrate [8]
OATP2B1 Transporter Info Organic anion transporting polypeptide 2B1 Substrate [7]
P-GP Transporter Info P-glycoprotein 1 Substrate [9]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP2 Transporter Info Km =617 microM Madin-Darby canine kidney cells (MDCKII)-MRP2 [5]
MRP3 Transporter Info Km =11.4 microM Spodoptera frugiperda (Sf9) cells-MRP3 [10]
P-GP Transporter Info Km =461 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [9]
P-GP Transporter Info Km =255 microM Madin-Darby canine kidney cells (MDCKII)-MDR1 [5]
References
1 Etoposide was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 ABCG1 and Pgp identify drug resistant, self-renewing osteosarcoma cells. Cancer Lett. 2019 Jul 1;453:142-157.
3 Characterization of 3-methoxy flavones for their interaction with ABCG2 as suggested by ATPase activity. Biochim Biophys Acta. 2014 Nov;1838(11):2929-38.
4 Multidrug resistance-associated protein-1 functional activity in Calu-3 cells. J Pharmacol Exp Ther. 2001 Sep;298(3):1199-205.
5 Delineating the contribution of secretory transporters in the efflux of etoposide using Madin-Darby canine kidney (MDCK) cells overexpressing P-glycoprotein (Pgp), multidrug resistance-associated protein (MRP1), and canalicular multispecific organic anion transporter (cMOAT). Drug Metab Dispos. 2002 Apr;30(4):457-63.
6 Functional reconstitution of human ABCC3 into proteoliposomes reveals a transport mechanism with positive cooperativity. Biochemistry. 2009 May 26;48(20):4423-30.
7 Identification of drugs and drug metabolites as substrates of multidrug resistance protein 2 (MRP2) using triple-transfected MDCK-OATP1B1-UGT1A1-MRP2 cells. Br J Pharmacol. 2012 Mar;165(6):1836-1847.
8 Effect of pregnane X receptor ligands on transport mediated by human OATP1B1 and OATP1B3. Eur J Pharmacol. 2008 Apr 14;584(1):57-65.
9 Efflux ratio cannot assess P-glycoprotein-mediated attenuation of absorptive transport: asymmetric effect of P-glycoprotein on absorptive and secretory transport across Caco-2 cell monolayers. Pharm Res. 2003 Aug;20(8):1200-9.
10 Characterization of drug transport by the human multidrug resistance protein 3 (ABCC3). J Biol Chem. 2001 Dec 7;276(49):46400-7.

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