Product Name

Etoposide

CAS Number

33419-42-0

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Product Name:
Etoposide
CAS Number:
33419-42-0
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.
Mode of Action:

Etoposide inhibits DNA topoisomerase II, thereby inhibiting DNA re-ligation. This causes critical errors in DNA synthesis at the premitotic stage of cell division and can lead to apoptosis of the cancer cell.. Etoposide is cell cycle dependent and phase specific, affecting mainly the S and G2 phases of cell division.

Pharmacodynamics:

Etoposide is an antineoplastic agent and an epipodophyllotoxin (a semisynthetic derivative of the podophyllotoxins). It inhibits DNA topoisomerase II, thereby ultimately 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.

Metabolism:

Primarily hepatic (through O-demethylation via the CYP450 3A4 isoenzyme pathway) with 40% excreted unchanged in the urine.

Toxicity:

Side effects include alopecia, constipation, diarrhea, nausea and vomiting and secondary malignancies (leukemia).

IUPAC:
(10R, 11R, 15R, 16S)-16-{[(2R, 4aR, 6R, 7R, 8R, 8aS)-7, 8-dihydroxy-2-methyl-hexahydro-2H-pyrano[3, 2-d][1, 3]dioxin-6-yl]oxy}-10-(4-hydroxy-3, 5-dimethoxyphenyl)-4, 6, 13-trioxatetracyclo[7.7.0.0, {3, 7}.0, {11, 15}]hexadeca-1(9), 2, 7-trien-12-one
ATC:
L01CB01
PubChem:
36462
DrugBank:
DB00773 (APRD00239)
Formula:
C22H28N2O
Molecular Mass:
588.5566
Synonyms:
(-)-Etoposide Etoposidum [INN-Latin] trans-Etoposide
SMILES:
COC1=CC(=CC(OC)=C1O)[C@H]1[C@@H]2[C@H](COC2=O)[C@H](O[C@@H]2O[C@@H]3CO[C@@H](C)O[C@H]3[C@H](O)[C@H]2O)C2=CC3=C(OCO3)C=C12
AHFS Code:
10:00.0
InChi:
VJJPUSNTGOMMGY-MRVIYFEKSA-N

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