Teniposide is a semisynthetic epipodophyllotoxin derivative and antineoplastic API. It is structurally related to etoposide and acts primarily by inhibiting DNA topoisomerase II. Teniposide stabilizes the topoisomerase II–DNA complex, resulting in DNA strand breaks and inhibition of DNA replication and repair.
Teniposide is used as an anticancer agent, particularly in combination chemotherapy. The historical U.S. FDA labeling for VUMON (teniposide injection) identifies its indication, in combination with other approved anticancer agents, for induction therapy in patients with refractory childhood acute lymphoblastic leukemia (ALL).
The API is a complex semisynthetic podophyllotoxin derivative with the molecular formula C32H32O13S and molecular weight approximately 656.66 g/mol. PubChem identifies CAS 29767-20-2 and FDA GSRS UNII 957E6438QA.
| Parameter | Value |
|---|---|
| API Name | Teniposide |
| CAS No. | 29767-20-2 |
| FDA UNII | 957E6438QA |
| Molecular Formula | C32H32O13S |
| Molecular Weight | 656.66 g/mol |
| Molecular Type | Semisynthetic small-molecule API |
| Therapeutic Class | Antineoplastic |
| Pharmacological Class | Topoisomerase II inhibitor |
| Related Compound | Etoposide |
| Alternative Names | VM-26, Teniposidum |
| Brand Reference | Vumon |
Teniposide is a semisynthetic derivative of podophyllotoxin. It contains a podophyllotoxin-related polycyclic structure with a thiophene-containing glycosidic moiety. The sulfur-containing structural modification distinguishes teniposide from etoposide.
Its molecular formula is C32H32O13S, with a molecular weight of 656.66 g/mol. PubChem reports an exact mass of 656.1564 Da and a calculated XlogP3 of approximately 1.2.
Teniposide is a crystalline solid. Published reference data report a melting range around 242–246°C, while TCI reports approximately 247°C with decomposition. This should be regarded as a physical reference property rather than automatically used as a universal API release limit.
Teniposide primarily acts through inhibition of DNA topoisomerase II.
The drug forms a stabilized complex involving topoisomerase II and DNA. This interferes with the normal cleavage-and-religation cycle of topoisomerase II and leads to accumulation of DNA double-strand breaks.
The resulting DNA damage interferes with replication and cell-cycle progression and ultimately promotes cancer-cell death. Teniposide is particularly associated with activity during the S and G2 phases of the cell cycle.
Teniposide API is used for the manufacture of anticancer pharmaceutical preparations.
Major therapeutic application includes:
The FDA VUMON label specifically describes use in combination with other approved anticancer agents for induction therapy in patients with refractory childhood ALL.
Teniposide can be characterized using chromatographic and spectroscopic techniques.
Important analytical controls may include:
Historical analytical literature describes HPLC methods for quantitative determination of teniposide, including UV detection at 240 nm for analytical determination in biological samples.
For pharmaceutical API release, the manufacturer's validated specification should be used rather than transferring analytical conditions from plasma-assay methods directly into a drug-substance specification.
Teniposide is a semisynthetic API derived from the podophyllotoxin/etoposide chemical framework rather than a recombinant biologic.
Manufacturing controls should address:
TCI currently lists Teniposide at minimum 98.0 area% by HPLC and a specific rotation specification of −107.0° to −115.0° at 20°C, c=1 in chloroform:methanol 9:1. These are TCI's product specifications, not a universal pharmacopoeial release specification.
PubChem describes Teniposide as practically insoluble in water.
Teniposide is practically insoluble in water. Historical pharmaceutical references describe it as insoluble in water and diethyl ether, slightly soluble in methanol, and very soluble in acetone and dimethylformamide.
The estimated aqueous solubility reported by PubChem/EPI is approximately 5.98 × 10⁻² g/L, but this is an estimated/reference physicochemical value and should not be entered as a pharmaceutical release specification.
Teniposide is sensitive to environmental conditions and should be handled according to the validated API storage specification.
A current TCI research-grade product listing specifies storage at −20°C and identifies the material as heat-sensitive. This is a supplier-specific research-product storage condition and should not automatically be represented as the storage requirement for commercial pharmaceutical API.
For commercial pharmaceutical manufacturing, storage conditions should follow the manufacturer's validated stability data and Certificate of Analysis.
A pharmaceutical Teniposide API manufacturer should provide appropriate documentation such as:
| Parameter | Specification |
|---|---|
| Appearance | white to off-white crystalline powder |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | NLT 98.0% |
| Specific Rotation | −107.0° to −115.0° |
| Melting Point | 242–246°C |