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{{Short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 383487454 |
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| verifiedrevid = 408925000 |
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| IUPAC_name = (5''R'',5a''R'',8a''R'',9''S'')-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-({4,6-''O''--β-<small>D</small>-glucopyranosyl}oxy)furonaphtho-1,3-dioxol-6(5a''H'')-one |
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| IUPAC_name = (5''R'',5a''R'',8a''R'',9''S'')-5,8,8a,9-Tetrahydro-5-(4-hydroxy-3,5-dimethoxyphenyl)-9-({4,6-''O''--β-<small>D</small>-glucopyranosyl}oxy)furonaphtho-1,3-dioxol-6(5a''H'')-one |
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| image = Teniposide.png |
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| image = Teniposide2DACS.svg |
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<!--Clinical data--> |
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| CASNo_Ref = {{cascite}} |
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| tradename = Vumon |
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| Drugs.com = {{drugs.com|monograph|teniposide}} |
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| MedlinePlus = a692045 |
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| pregnancy_AU = D |
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| pregnancy_US = D |
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| legal_US = Rx-only |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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| bioavailability = N/A |
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| protein_bound = >99% |
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| metabolism = ] (]-mediated) |
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| elimination_half-life = 5 hours |
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| excretion = ] and fecal |
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<!--Identifiers--> |
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| IUPHAR_ligand = 6843 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 29767-20-2 |
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| CAS_number = 29767-20-2 |
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| ATC_prefix = L01 |
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| ATC_prefix = L01 |
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| ATC_suffix = CB02 |
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| ATC_suffix = CB02 |
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| PubChem = 34698 |
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| PubChem = 34698 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = APRD00649 |
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| DrugBank = DB00444 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 31930 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 957E6438QA |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 75988 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02698 |
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| KEGG = D02698 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| C = 32 | H = 32 | O = 13 | S = 1 |
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| ChEMBL = 1200536 |
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| molecular_weight = 656.655 g/mol |
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| synonyms = VM-26 |
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| bioavailability = n/a |
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<!--Chemical data--> |
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| protein_bound = >99% |
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| C=32 | H=32 | O=13 | S=1 |
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| metabolism = ] (]-mediated) |
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| smiles = COc1cc(cc(c1O)OC)2c3cc4c(cc3(52C(=O)OC5)O6((7(O6)COC(O7)c8cccs8)O)O)OCO4 |
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| elimination_half-life = 5 hours |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| excretion = ] and fecal |
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| StdInChI=1S/C32H32O13S/c1-37-19-6-13(7-20(38-2)25(19)33)23-14-8-17-18(42-12-41-17)9-15(14)28(16-10-39-30(36)24(16)23)44-32-27(35)26(34)29-21(43-32)11-40-31(45-29)22-4-3-5-46-22/h3-9,16,21,23-24,26-29,31-35H,10-12H2,1-2H3/t16-,21+,23+,24-,26+,27+,28+,29+,31?,32-/m0/s1 |
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| pregnancy_AU = D |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| pregnancy_US = D |
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| StdInChIKey = NRUKOCRGYNPUPR-PSZSYXFXSA-N |
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| legal_US = Rx-only |
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| routes_of_administration = ] |
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}} |
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}} |
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'''Teniposide''' ('''Vumon''', '''VM-26''') is a ] ] mainly used in the treatment of childhood ] (ALL). It is in a class of drugs known as ] derivatives and slows the growth of ] cells in the body. |
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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 = 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> |
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==Mechanism of action== |
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==Medical uses== |
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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 ] drugs.<ref name="Drugs.com" /> In Europe, it is also approved for the treatment of Hodgkin's lymphoma, generalized ], ] ], acute ], primary brain tumours (], ], ]), ], ] and other solid tumours in children.<ref name="Austria-Codex" /> |
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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 ] 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. |
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==Administration== |
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===Administration=== |
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The medication is ] and burns if it leaks under the skin. It is sometimes used in combination with other anticancer drugs. |
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The medication is ] and burns if it leaks under the skin. It can be used in combination with other anticancer drugs.<ref name="Austria-Codex" /> |
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==Contraindications== |
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==Side-effects== |
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The drug is contraindicated during pregnancy and ], in patients with severe liver or kidney impairment or severely impaired ].<ref name="Austria-Codex" /> |
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Teniposide, when used with other chemotherapeutic agents for the treatment of ALL, results in severe ]. Other common side effects include ], ] reactions, and ]. |
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==Side effects== |
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Teniposide, when used with other chemotherapeutic agents for the treatment of ALL, results in severe ]. Other common side effects include ] toxicity, ] reactions, and reversible ].<ref name="Austria-Codex" /> |
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== Interactions == |
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No systematic interaction studies are available. The ]s ] and ] have been found to lower its blood plasma concentrations.<ref name="Mutschler" /> Theoretically possible interactions include increased plasma concentrations when combined with ], ] or ], which displace teniposide from ], at least '']''.<ref name="Austria-Codex" /><ref name="Drugs.com" /> |
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==Pharmacology== |
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===Mechanism of action=== |
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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}} |
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==Chemistry== |
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], showing part of the ] (at bottom)]] |
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Teniposide is a ] derivative of ]<ref name="Austria-Codex" /> from the ] of the ] (''Podophyllum peltatum''). More specifically, it is a ] of podophyllotoxin with a <small>D</small>-] derivative. It is chemically similar to the anti-cancer drug ], being distinguished only by a ] rest where etoposide has a methyl.<ref name="Mutschler" /> Both these compounds have been developed with the aim of creating less toxic derivatives of podophyllotoxin.<ref>{{cite book |title=Arzneistoff-Profile | veditors = Dinnendahl V, Fricke U |publisher=Govi Pharmazeutischer Verlag |location=Eschborn, Germany |date=2015 |edition=28th |volume=4 |isbn=978-3-7741-9846-3 |language=German }}</ref> |
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== References == |
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{{Reflist|35em}} |
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{{Chemotherapeutic agents}} |
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{{Chemotherapeutic agents}} |
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{{antineoplastic-drug-stub}} |
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