Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Semaxanib: Difference between pages
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Saving copy of the {{drugbox}} taken from revid 457315489 of page Semaxanib for the Chem/Drugbox validation project (updated: 'CAS_number'). |
m Disambiguating links to Hypoxia (link changed to Hypoxia (medical)) using DisamAssist. |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:Semaxanib|oldid=457315489}} 457315489] of page [[Semaxanib]] with values updated to verified values.}} |
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{{Distinguish|Semax}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 464389051 |
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| IUPAC_name = (3''Z'')-3-[(3,5-dimethyl-1''H''-pyrrol-2-yl)methylidene]-1,3-dihydro-2''H''-indol-2-one |
| IUPAC_name = (3''Z'')-3-[(3,5-dimethyl-1''H''-pyrrol-2-yl)methylidene]-1,3-dihydro-2''H''-indol-2-one |
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| image = Semaxanib.svg |
| image = Semaxanib.svg |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> |
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| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> |
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| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> |
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| legal_status = |
| legal_status = |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| protein_bound = |
| protein_bound = |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 5056 |
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| CAS_number_Ref = {{cascite| |
| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = |
| CAS_number = 194413-58-6 |
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| ATC_prefix = none |
| ATC_prefix = none |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = 5329098 |
| PubChem = 5329098 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
| DrugBank = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4486260 |
| ChemSpiderID = 4486260 |
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| |
| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 91083 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 71IA9S35AJ |
| UNII = 71IA9S35AJ |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=15 | H=14 | N=2 | O=1 |
| C=15 | H=14 | N=2 | O=1 |
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⚫ | |||
| molecular_weight = 238.285 g/mol |
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⚫ | |||
| InChI = 1/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8- |
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| InChIKey = WUWDLXZGHZSWQZ-WQLSENKSBZ |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8- |
| StdInChI = 1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8- |
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| StdInChIKey = WUWDLXZGHZSWQZ-WQLSENKSSA-N |
| StdInChIKey = WUWDLXZGHZSWQZ-WQLSENKSSA-N |
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}} |
}} |
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'''Semaxanib''' ([[International Nonproprietary Name|INN]],<ref>{{cite journal | author = World Health Organization | author-link = World Health Organization | title = International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed INN: List 85 | journal = WHO Drug Information | volume = 15 | issue = 2 | year = 2001}} {{cite web |url=https://www.who.int/druginformation/vol15num2_2001/list_85.pdf |title= Full text |url-status= dead |archive-url= https://web.archive.org/web/20070316041248/http://www.who.int/druginformation/vol15num2_2001/list_85.pdf |archive-date= 2007-03-16 }} {{small|(244 [[Kibibyte|KiB]])}}</ref> codenamed '''SU5416''') is a [[tyrosine-kinase inhibitor]] drug designed by [[SUGEN]] as a cancer therapeutic. It is an [[investigational new drug|experimental stage drug]], not [[Regulation of therapeutic goods|licensed]] for use on human patients outside [[clinical trial]]s. |
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Semaxanib is a potent and selective synthetic [[kinase inhibitor|inhibitor]] of the Flk-1/KDR [[vascular endothelial growth factor]] (VEGF) receptor [[tyrosine kinase]]. It targets the [[VEGF pathway]], and both ''[[in vivo]]'' and ''[[in vitro]]'' studies have demonstrated [[antiangiogenic]] potential.{{cn|date=February 2023}} |
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==Research== |
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In February 2002, [[Pharmacia]], the then-parent of Sugen, prematurely ended [[Clinical trial#Phase III|phase III]] clinical trials of semaxinib in the treatment of advanced [[colorectal cancer]] due to discouraging results.<ref>{{cite press release | url = http://www.prnewswire.com/cgi-bin/stories.pl?ACCT=104&STORY=/www/story/02-08-2002/0001665238&EDATE= | title = Pharmacia Announces Closing of SU5416 (semaxanib) Clinical Trials | date = February 8, 2002 | access-date = 2007-03-20}}</ref> Other studies, at earlier phases, have since been conducted.<ref>{{cite journal | vauthors = O'Donnell A, Padhani A, Hayes C, Kakkar AJ, Leach M, Trigo JM, Scurr M, Raynaud F, Phillips S, Aherne W, Hardcastle A, Workman P, Hannah A, Judson I | title = A Phase I study of the angiogenesis inhibitor SU5416 (semaxanib) in solid tumours, incorporating dynamic contrast MR pharmacodynamic end points | journal = British Journal of Cancer | volume = 93 | issue = 8 | pages = 876–83 | date = October 2005 | pmid = 16222321 | pmc = 2361651 | doi = 10.1038/sj.bjc.6602797 }}</ref><ref>{{cite journal | vauthors = Lockhart AC, Cropp GF, Berlin JD, Donnelly E, Schumaker RD, Schaaf LJ, Hande KR, Fleischer AC, Hannah AL, Rothenberg ML | title = Phase I/pilot study of SU5416 (semaxinib) in combination with irinotecan/bolus 5-FU/LV (IFL) in patients with metastatic colorectal cancer | journal = American Journal of Clinical Oncology | volume = 29 | issue = 2 | pages = 109–15 | date = April 2006 | pmid = 16601426 | doi = 10.1097/01.coc.0000199882.53545.ac | s2cid = 26566099 }}</ref> However, due to the prospect of next-generation tyrosine kinase inhibitors and the inefficacy of semaxanib in clinic trials, further development of the drug has been discontinued.<ref>{{cite journal | vauthors = Hoff PM, Wolff RA, Bogaard K, Waldrum S, Abbruzzese JL | title = A Phase I study of escalating doses of the tyrosine kinase inhibitor semaxanib (SU5416) in combination with irinotecan in patients with advanced colorectal carcinoma | journal = Japanese Journal of Clinical Oncology | volume = 36 | issue = 2 | pages = 100–3 | date = February 2006 | pmid = 16449240 | doi = 10.1093/jjco/hyi229 | doi-access = free }}</ref> A related compound, SU11248 ([[sunitinib]]), was further developed by Sugen and subsequently by [[Pfizer]], and received FDA approval for treatment of renal carcinoma in January 2006.<ref name="FDA">{{cite web | publisher = U.S. [[Food and Drug Administration]] (FDA) | title = FDA approves new treatment for gastrointestinal and kidney cancer | url=https://www.fda.gov/bbs/topics/news/2006/NEW01302.html | archive-url=https://web.archive.org/web/20060203031129/http://www.fda.gov/bbs/topics/news/2006/NEW01302.html | url-status=dead | archive-date=3 February 2006 |year=2006 }}</ref> |
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When combined with chronic exposure to [[Hypoxia (medical)|hypoxia]], SU5416 induces severe [[pulmonary hypertension]] in [[laboratory mouse|mice]] and [[laboratory rat|rat]]s. This property has been exploited to develop a series of useful, though controversial, [[animal testing on rodents|rodent models]] of pulmonary arterial hypertension, the first and best characterized being the Sugen/Hypoxia (SuHx) mouse model.<ref>{{cite journal |vauthors=Vitali SH, Hansmann G, Rose C, Fernandez-Gonzalez A, Scheid A, Mitsialis SA, Kourembanas S |title=The Sugen 5416/hypoxia mouse model of pulmonary hypertension revisited: long-term follow-up |journal=Pulm Circ |volume=4 |issue=4 |pages=619–29 |date=December 2014 |pmid=25610598 |pmc=4278622 |doi=10.1086/678508}}</ref><ref>{{cite journal |vauthors=Voelkel NF, Bogaard HJ |title=Sugen, hypoxia and the lung circulation |journal=Pulm Circ |volume=11 |issue=4 |pages=20458940211051188 |date=2021 |pmid=34631012 |pmc=8493318 |doi=10.1177/20458940211051188}}</ref> |
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== References == |
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{{Reflist|2}} |
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{{Extracellular chemotherapeutic agents}} |
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{{Growth factor receptor modulators}} |
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[[Category:Receptor tyrosine kinase inhibitors]] |
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[[Category:Experimental cancer drugs]] |
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[[Category:Indolines]] |
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[[Category:Lactams]] |
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[[Category:Pyrroles]] |
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[[Category:Oxindoles]] |
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{{antineoplastic-drug-stub}} |