Compound Information | SONAR Target prediction |
Name: | ETOPOSIDE |
Unique Identifier: | SPE01500903 |
MolClass: | Checkout models in ver1.5 and ver1.0 |
Molecular Formula: | |
Molecular Weight: | 556.302 g/mol |
X log p: | 9.942 (online calculus) |
Lipinksi Failures | 2 |
TPSA | 100.14 |
Hydrogen Bond Donor Count: | 0 |
Hydrogen Bond Acceptors Count: | 13 |
Rotatable Bond Count: | 5 |
Canonical Smiles: | COc1cc(cc(OC)c1O)C1C2C(COC2=O)C(OC2OC3COC(C)OC3C(O)C2O)c2cc3OCOc3cc12 |
Class: | lignan |
Source: | semisynthetic |
Therapeutics: | antineoplastic |
Generic_name: | Etoposide |
Chemical_iupac_name: | 4--demethyl-epipodophyllotoxin 9-[4,6-O-(R)-ethylidene-beta-D-glucopyranoside], 4--(dihydrogen phosphate) |
Drug_type: | Approved Drug |
Pharmgkb_id: | PA449552 |
Kegg_compound_id: | C01576 |
Drugbank_id: | APRD00239 |
Melting_point: | 236-251 oC |
H2o_solubility: | 58.7 mg/L |
Logp: | 1.197 |
Cas_registry_number: | 33419-42-0 |
Drug_category: | Antineoplastic Agents, Phytogenic; Nucleic Acid Synthesis Inhibitors; ATC:L01CB01 |
Indication: | For use in combination with other chemotherapeutic agents in the treatment of refractory testicular tumors and as first line treatment in patients with small cell lung cancer. Also used to treat other malignancies such as lymphoma, non-lymphocytic leukemia, and glioblastoma multiforme. |
Pharmacology: | Etoposide is an antineoplastic agent and an epipodophyllotoxin (a semisynthetic derivative of the podophyllotoxins). It inhibits DNA topoisomerase II, thereby inhibiting DNA synthesis. Etoposide is cell cycle dependent and phase specific, affecting mainly the S and G2 phases. Two different dose-dependent responses are seen. At high concentrations (10 µg/mL or more), lysis of cells entering mitosis is observed. At low concentrations (0.3 to 10 µg/mL), cells are inhibited from entering prophase. It does not interfere with microtubular assembly. The predominant macromolecular effect of etoposide appears to be the induction of DNA strand breaks by an interaction with DNA-topoisomerase II or the formation of free radicals. |
Mechanism_of_action: | Etoposide inhibits DNA topoisomerase II, thereby inhibiting DNA synthesis at the premitotic stage of cell division. Etoposide is cell cycle dependent and phase specific, affecting mainly the S and G2 phases of cell division. |
Organisms_affected: | Humans and other mammals |