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Latest revision as of 23:35, 5 April 2023 edit undoEntranced98 (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers173,133 edits Importing Wikidata short description: "Chemical compound"Tag: Shortdesc helper |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 451225194 |
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| verifiedrevid = 451724973 |
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| IUPAC_name = Phosphoric acid mono-{2-methoxy-5--phenyl} ester |
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| IUPAC_name = Phosphoric acid mono-<nowiki/>{2-methoxy-5--phenyl} ester |
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| image = Combretastatin A-4 phosphate.svg |
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| image = Fosbretabulin.svg |
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| alt = |
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| alt = |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
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| pregnancy_category = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
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| legal_status = Investigational |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = |
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| CAS_number = 222030-63-9 |
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| ATCvet = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = I5590ES2QZ |
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| ATCvet = |
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| ATC_prefix = <!-- 'none' if uncategorised --> |
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| ATC_prefix = <!-- 'none' if uncategorised --> |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 5351387 |
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| PubChem = 5351387 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChemSpiderID = 4508406 |
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| smiles = O=P(O)(O)Oc1c(OC)ccc(c1)\C=C/c2cc(OC)c(OC)c(OC)c2 |
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| StdInChI = 1S/C18H21O8P/c1-22-14-8-7-12(9-15(14)26-27(19,20)21)5-6-13-10-16(23-2)18(25-4)17(11-13)24-3/h5-11H,1-4H3,(H2,19,20,21)/b6-5- |
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| StdInChIKey = WDOGQTQEKVLZIJ-WAYWQWQTSA-N |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=18 | H=21 | O=8 | P=1 |
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| C=18 | H=21 | O=8 | P=1 |
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| synonyms = Combretastatin A-4 phosphate; CA4P; CA4PD; fosbretabulin disodium; fosbretabulin tromethamine |
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| molecular_weight = 396.32 g/mol (exact mass : 396.097404) |
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| synonyms = CA4P<br>CA4PD |
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}} |
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:''For more information about this drug and its actions, see ].'' |
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'''Combretastatin A-4 phosphate''' (and its disodium salt) is a microtubule destabilizing drug, a type of ], a drug designed to damage the vasculature (blood vessels) of cancer tumors causing central necrosis. It is a derivative of ]. |
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'''Fosbretabulin''' (also known as '''combretastatin A-4 phosphate''' or '''CA4P''') is a microtubule destabilizing experimental drug, a type of ], a drug designed to damage the vasculature (blood vessels) of cancer tumours causing central necrosis. It is a derivative of ]. It is ] as the ] fosbretabulin disodium and fosbretabulin tromethamine.<ref>{{ClinicalTrialsGov|NCT02132468 |A Ph 2 Study to Investigate the Safety and Activity of Fosbretabulin Tromethamine (CA4P) in the Treatment of Well-Differentiated, Low-to-Intermediate-Grade Unresectable, Recurrent or Metastatic PNET or GI-NET Neuroendocrine Tumors/Carcinoid With Elevated Biomarkers}}</ref> |
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Combretastatin A-4 phosphate is a ]. In vivo, it is dephosphorylated to its active metabolite, ].<ref></ref> |
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Fosbretabulin is a ]. '']'', it is dephosphorylated to its ], ].<ref>{{cite web | url = http://www.cancer.gov/drugdictionary/?CdrID=43316 | title = Fosbretabulin disodium | work = |
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National Cancer Institute | publisher = U.S. Department of Health and Human Services }}</ref> |
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In July 2007, the pharmaceutical company ] initiated a 180-patient phase III clinical trial of fosbretabulin in combination with ] for the treatment of ].<ref>{{ClinicalTrialsGov|NCT00507429|A Phase II/III Study to Evaluate the Safety and Efficacy of Combretastatin A-4 Phosphate in Combination With Paclitaxel and Carboplatin in Comparison With Paclitaxel and Carboplatin Against Anaplastic Thyroid Carcinoma }}</ref> There is currently no fully FDA approved treatment for this form of cancer. By 2017, it had completed multiple clinical trials (e.g. for solid tumours,<ref>{{ClinicalTrialsGov|NCT00113438|A Randomized Open-Labeled Phase II Study of Combretastatin A-4 Phosphate in Combination With Paclitaxel and Carboplatin to Evaluate the Safety and Efficacy in Subjects With Advanced Imageable Malignancies}}</ref> non-small cell lung cancer<ref>{{ClinicalTrialsGov|NCT00653939|A Phase II Study to Assess the Safety and Efficacy of the Combination of Carboplatin, Paclitaxel, and Bevacizumab ± Combretastatin A4 Phosphate (CA4P) Followed by Bevacizumab ± CA4P in Subjects With Chemotherapy Naïve Stage IIIB/IV Non-Squamous Cell Histology Non-Small Cell Lung Cancer (NSCLC)}}</ref>) with more in progress.<ref>{{Cite web|url=https://clinicaltrials.gov/ct2/results?term=CA4P&Search=Search|title=Search of: CA4P - List Results - ClinicalTrials.gov|website=clinicaltrials.gov}}</ref> |
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==See also== |
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* ], e.g. for the chemical synthesis |
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==References== |
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==References== |
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