Etoposide

Structural formula
General
Non-proprietary name	Etopsid
other names	VP-16; VP16; ETO; 4′-desmethylepipodophyllotoxin- (4,6- O -ethylidene-glucoside);
Molecular formula	C 29 H 32 O 13
Brief description	colorless solid
External identifiers / databases
EC number	251-509-1
ECHA InfoCard	100,046,812
PubChem	36462
DrugBank	DB00773
Wikidata	Q418817
Drug information
ATC code	L01 CB01
Drug class	Cytostatic
Mechanism of action	Topoisomerase II inhibitors
properties
Molar mass	588.57 g mol −1
Physical state	firmly
Melting point	236-251 ° C
pK s value	9.8
solubility	good in DMSO ; bad in water;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 302-350-361d-412
	P: 201-264-273-280-308 + 313-501
Toxicological data	15.07 mg kg −1 ( LD 50 , mouse , iv ) ; 215 mg kg −1 ( LD 50 , mouse , oral ) ; 75 mg kg −1 ( LD 50 , rat , iv ) ; 1784 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Etoposide is a glycoside of podophyllotoxin , which is obtained from the roots of the evergreen American May apple ( Podophyllum peltatum ).

pharmacology

Etoposide is used chemically unchanged or in the form of its phosphoric acid ester ( etoposide phosphate ) as a cytostatic in chemotherapy . It inhibits the enzyme topoisomerase II and suppresses cytokinesis . This leads to the fact that the cell reaches the stage of apoptosis and dies. Furthermore, etoposide also leads to single and double strand breaks in the DNA , which increases the cytotoxicity even more.

The main side effects of chemotherapy are allergies , peripheral neuropathy , hypotension , bronchospasm and mild liver dysfunction.

A very similar compound is the semi-synthetic teniposide , which can be made from podophyllotoxin.

Trade names

Monopreparations

Eto-cell (D), Eto-Gry (D), Etomedac (D), Etopophos (D, A, CH), Lastet (D), Neoposid (D), Riboposid (D), Vepesid (D, A, CH , USA), various generics (D, A, CH)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on etoposide. In: Römpp Online . Georg Thieme Verlag, accessed on March 15, 2011.
↑ ^a ^b ^c Datasheet Etoposide from Sigma-Aldrich , accessed on November 3, 2019 ( PDF ).
^ ^A ^b ^c F. von Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. Vol. 8 fabrics E-O 5th edition, pp. 152-154, Birkhäuser, 1991, ISBN 978-3-540-52688-9 .
↑ External identifiers or database links for etoposide phosphate: CAS number: 117091-64-2, EC number: 630-364-1, ECHA InfoCard: 100.158.659 , PubChem : 6918092 , ChemSpider : 5293306 , Wikidata : Q27260984 .
↑ Red List Online, as of August 2009.
↑ AM comp. d. Switzerland, as of August 2009.
↑ AGES-PharmMed, as of August 2009.

[RÖMPP-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on etoposide. In: Römpp Online . Georg Thieme Verlag, accessed on March 15, 2011.

[Sigma-2] Datasheet Etoposide from Sigma-Aldrich , accessed on November 3, 2019 ( PDF ).

[hager-3] A ^b ^c F. von Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hagers Handbook of Pharmaceutical Practice. Vol. 8 fabrics E-O 5th edition, pp. 152-154, Birkhäuser, 1991, ISBN 978-3-540-52688-9 .

[4] External identifiers or database links for etoposide phosphate: CAS number: 117091-64-2, EC number: 630-364-1, ECHA InfoCard: 100.158.659 , PubChem : 6918092 , ChemSpider : 5293306 , Wikidata : Q27260984 .

[5] Red List Online, as of August 2009.

[6] AM comp. d. Switzerland, as of August 2009.

[7] AGES-PharmMed, as of August 2009.