Podophyllotoxin
| Structural formula | ||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
||||||||||||||||||||||
| General | ||||||||||||||||||||||
| Surname | Podophyllotoxin | |||||||||||||||||||||
| Molecular formula | C 22 H 22 O 8 | |||||||||||||||||||||
| Brief description |
White dust |
|||||||||||||||||||||
| External identifiers / databases | ||||||||||||||||||||||
|
||||||||||||||||||||||
| Drug information | ||||||||||||||||||||||
| ATC code | ||||||||||||||||||||||
| Drug class | ||||||||||||||||||||||
| Mechanism of action |
Mitosis inhibitors |
|||||||||||||||||||||
| properties | ||||||||||||||||||||||
| Molar mass | 414.41 g · mol -1 | |||||||||||||||||||||
| Physical state |
firmly |
|||||||||||||||||||||
| Melting point |
183 ° C |
|||||||||||||||||||||
| safety instructions | ||||||||||||||||||||||
|
||||||||||||||||||||||
| Toxicological data | ||||||||||||||||||||||
| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
Podophyllotoxin is a drug from the group of lignans that is obtained from the rootstock of the foot leaf (syn .: May apple, duck foot, Podophyllum peltatum L. ) and is approved for topical use for the treatment of genital warts in the external genital area.
Clinical information
Medicines containing podophyllotoxin are used to treat genital warts in the external genital area. The application is carried out by the doctor, after initial application and careful instruction also by the patient himself by application to the skin in the form of a cream or solution.
The use of podophyllotoxin is contraindicated in children and adolescents, as well as in pregnant women and nursing mothers . In women, pregnancy should therefore be excluded before treatment; a reliable method of contraception must be used during treatment. The drug must also not be used in the event of hypersensitivity to the active ingredient podophyllotoxin; Avoid applying to open wounds. The consumption of alcohol during treatment can massively increase side effects and should therefore be avoided.
Local irritation may occur at the start of treatment; these are a consequence of the incipient wart necrosis . Occasionally, erosions and inflammatory reactions occur; Symptoms of glans inflammation or phimosis are rare.
The therapeutic effect usually occurs after three to four weeks of treatment. The success rate of such a treatment is 60–80%, relapses occur in 7–38% of all cases.
Pharmacological information
Podophyllotoxin is a powerful spindle poison which, by binding to tubulin, prevents the formation of microtubules in the spindle apparatus and thus blocks cell division . This causes necrosis of the warts.
Little is known about the uptake, distribution and degradation of the substance; the half-life should be around 1 to 4.5 hours. The acute toxicity of the substance has been well studied; the dose used for therapy is 100 times lower than the dose tolerated in animal experiments with local application. The mutagenicity has not been adequately investigated, but there is currently no evidence of carcinogenicity . Local application to the rat showed no teratogenic effects; however, teratogenic effects were observed after injection into the abdominal cavity or after subcutaneous application. Therefore, as a precautionary measure, its use during pregnancy is contraindicated.
Glycosides of podophyllotoxin such as teniposide and etoposide are used as cytostatics in cancer therapy.
Other Information
Commercially available podophyllotoxin preparations have an active ingredient concentration of 0.15% (Wartec® cream) to 0.5% (Condylox® solution). In contrast to the solution, the galenic form of the podophyllotoxin cream is said to be more patient-friendly due to its simpler application and better tolerance.
In terms of effectiveness and toxicity, podophyllotoxin is rated significantly more favorably than the crude product podophyllin, which was previously also used for pharmaceutical preparations . In contrast to this, podophyllotoxin showed neither a mutagenic nor a carcinogenic effect in clinical studies, and no cytotoxic effects could be demonstrated. In contrast to drugs containing podophyllin, there is no risk of systemic toxicity or severe local side effects. The use of podophyllin preparations is therefore now considered obsolete.
Trade names
Condyline (CH), Condylox (D, A), Warix (CH), Wartec (D)
literature
- L. Roth, M. Daunderer & K. Kormann: Poison plants - plant poisons. Nikol Verlagsgesellschaft, 1994, page 576, ISBN 3-933203-31-7
Web links
Individual evidence
- ↑ a b c data sheet podophyllotoxin from Sigma-Aldrich , accessed on November 5, 2016 ( PDF ).
- ↑ a b Entry on podophyllotoxin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
- ↑ a b c d Specialist information Condylox.
