Teniposide

Teniposide

Systematic (IUPAC) name
(5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-({4,6-O-[(R)-2-thienylmethylene]-β-D-glucopyranosyl}oxy)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a692045
Pregnancy cat.	D(AU) D(US)
Legal status	℞-only (US)
Routes	Intravenous
Pharmacokinetic data
Bioavailability	n/a
Protein binding	>99%
Metabolism	Hepatic (CYP2C19-mediated)
Half-life	5 hours
Excretion	Renal and fecal
Identifiers
CAS number	29767-20-2 Y
ATC code	L01CB02
PubChem	CID 34698
DrugBank	APRD00649
ChemSpider	31930 N
UNII	957E6438QA N
KEGG	D02698 Y
ChEMBL	CHEMBL1200536 N
Chemical data
Formula	C32H32O13S
Mol. mass	656.655 g/mol
N(what is this?)  (verify)

Teniposide (Vumon, VM-26) is a chemotherapeutic medication mainly used in the treatment of childhood acute lymphocytic leukemia (ALL). It is in a class of drugs known as podophyllotoxin derivatives and slows the growth of cancer cells in the body.

Mechanism of action

Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA-protein cross-links. The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate.

Administration

The medication is injected though a vein and burns if it leaks under the skin. It is sometimes used in combination with other anticancer drugs.

Side-effects

Teniposide, when used with other chemotherapeutic agents for the treatment of ALL, results in severe myelosuppression. Other common side effects include gastrointestinal toxicity, hypersensitivity reactions, and alopecia.