| Revision as of 12:36, 1 June 2023 editGraeme Bartlett (talk | contribs)Administrators250,279 edits added Category:Methoxy compounds using HotCat← Previous edit | Latest revision as of 17:51, 18 August 2023 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,966 edits consistent citation formatting | ||
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| | StdInChIKey = NRUKOCRGYNPUPR-PSZSYXFXSA-N | | StdInChIKey = NRUKOCRGYNPUPR-PSZSYXFXSA-N | ||
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| '''Teniposide''' (trade name '''Vumon''') is a ] ]<ref>{{cite journal | vauthors = Cragg GM, Newman DJ | title = Plants as a source of anti-cancer agents | journal = Journal of Ethnopharmacology | volume = 100 | issue = 1–2 | pages = |
'''Teniposide''' (trade name '''Vumon''') is a ] ]<ref>{{cite journal | vauthors = Cragg GM, Newman DJ | title = Plants as a source of anti-cancer agents | journal = Journal of Ethnopharmacology | volume = 100 | issue = 1–2 | pages = 72–79 | date = August 2005 | pmid = 16009521 | doi = 10.1016/j.jep.2005.05.011 | url = https://zenodo.org/record/1259111 }}</ref> used in the treatment of childhood ] (ALL), ], certain ]s, and other types of cancer.<ref name="Austria-Codex">{{cite book|title=Austria-Codex| veditors = Jasek W|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2007|edition=62nd|pages=8855–6|isbn=978-3-85200-181-4|language=German}}</ref> It is in a class of drugs known as ] derivatives and slows the growth of ] cells in the body.<ref name="Drugs.com">Drugs.com: Teniposide {{drugs.com|monograph|teniposide}}.</ref> | ||
| ==Medical uses== | ==Medical uses== | ||
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| ===Mechanism of action=== | ===Mechanism of action=== | ||
| Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA-protein cross-links.<ref name="Austria-Codex" /> The substance has been found to act as an ] (an enzyme that aids in DNA unwinding),<ref name="Mutschler">{{Cite book | |
Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA-protein cross-links.<ref name="Austria-Codex" /> The substance has been found to act as an ] (an enzyme that aids in DNA unwinding),<ref name="Mutschler">{{Cite book | vauthors = Mutschler E, Schäfer-Korting M |title=Arzneimittelwirkungen |language=German |location=Stuttgart |publisher=Wissenschaftliche Verlagsgesellschaft |year=2001 |edition=8th |pages=894–5 |isbn=3-8047-1763-2 }}</ref><ref>{{cite journal | vauthors = de Jong S, Kooistra AJ, de Vries EG, Mulder NH, Zijlstra JG | title = Topoisomerase II as a target of VM-26 and 4'-(9-acridinylamino)methanesulfon-m-aniside in atypical multidrug resistant human small cell lung carcinoma cells | journal = Cancer Research | volume = 53 | issue = 5 | pages = 1064–1071 | date = March 1993 | pmid = 8382551 }}</ref> since it 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.{{citation needed|date=November 2015}} | ||
| ==Chemistry== | ==Chemistry== | ||
Latest revision as of 17:51, 18 August 2023
Chemical compound Pharmaceutical compound | |
| Clinical data | |
|---|---|
| Trade names | Vumon |
| Other names | VM-26 |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a692045 |
| Pregnancy category |
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| Routes of administration | Intravenous |
| ATC code | |
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| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | N/A |
| Protein binding | >99% |
| Metabolism | Hepatic (CYP2C19-mediated) |
| Elimination half-life | 5 hours |
| Excretion | Renal and fecal |
| Identifiers | |
IUPAC name
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.045.286  |
| Chemical and physical data | |
| Formula | C32H32O13S |
| Molar mass | 656.66 g·mol |
| 3D model (JSmol) | |
SMILES
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| (what is this?) (verify) | |
Teniposide (trade name Vumon) is a chemotherapeutic medication used in the treatment of childhood acute lymphocytic leukemia (ALL), Hodgkin's lymphoma, certain brain tumours, and other types of cancer. It is in a class of drugs known as podophyllotoxin derivatives and slows the growth of cancer cells in the body.
Medical uses
Teniposide is used for the treatment of a number of cancer types in children. In the US, it is approved for the second-line therapy of acute lymphocytic leukemia (ALL) in combination with other antineoplastic drugs. In Europe, it is also approved for the treatment of Hodgkin's lymphoma, generalized malignant lymphoma, reticulocyte sarcoma, acute leukaemia, primary brain tumours (glioblastoma, ependymoma, astrocytoma), bladder cancer, neuroblastoma and other solid tumours in children.
Administration
The medication is injected though a vein and burns if it leaks under the skin. It can be used in combination with other anticancer drugs.
Contraindications
The drug is contraindicated during pregnancy and lactation, in patients with severe liver or kidney impairment or severely impaired haematopoiesis.
Side effects
Teniposide, when used with other chemotherapeutic agents for the treatment of ALL, results in severe bone marrow suppression. Other common side effects include gastrointestinal toxicity, hypersensitivity reactions, and reversible alopecia.
Interactions
No systematic interaction studies are available. The enzyme inducers phenobarbital and phenytoin have been found to lower its blood plasma concentrations. Theoretically possible interactions include increased plasma concentrations when combined with sodium salicylate, sulfamethizole or tolbutamide, which displace teniposide from plasma protein binding, at least in vitro.
Pharmacology
Mechanism of action
Teniposide causes dose-dependent single- and double-stranded breaks in DNA and DNA-protein cross-links. The substance has been found to act as an inhibitor of topoisomerase II (an enzyme that aids in DNA unwinding), since it 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.
Chemistry
Teniposide is a semisynthetic derivative of podophyllotoxin from the rhizome of the wild mandrake (Podophyllum peltatum). More specifically, it is a glycoside of podophyllotoxin with a D-glucose derivative. It is chemically similar to the anti-cancer drug etoposide, being distinguished only by a thienyl rest where etoposide has a methyl. Both these compounds have been developed with the aim of creating less toxic derivatives of podophyllotoxin.
References
- Cragg GM, Newman DJ (August 2005). "Plants as a source of anti-cancer agents". Journal of Ethnopharmacology. 100 (1–2): 72–79. doi:10.1016/j.jep.2005.05.011. PMID 16009521.
- ^ Jasek W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 8855–6. ISBN 978-3-85200-181-4.
- ^ Drugs.com: Teniposide Monograph.
- ^ Mutschler E, Schäfer-Korting M (2001). Arzneimittelwirkungen (in German) (8th ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. pp. 894–5. ISBN 3-8047-1763-2.
- de Jong S, Kooistra AJ, de Vries EG, Mulder NH, Zijlstra JG (March 1993). "Topoisomerase II as a target of VM-26 and 4'-(9-acridinylamino)methanesulfon-m-aniside in atypical multidrug resistant human small cell lung carcinoma cells". Cancer Research. 53 (5): 1064–1071. PMID 8382551.
- Dinnendahl V, Fricke U, eds. (2015). Arzneistoff-Profile (in German). Vol. 4 (28th ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.