| Revision as of 20:00, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 457804030 of page Aclarubicin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number'). |
Latest revision as of 07:07, 5 November 2024 edit Citation bot (talk | contribs)Bots5,424,091 edits Altered title. Add: pages, issue, volume. | Use this bot. Report bugs. | Suggested by Dominic3203 | #UCB_webform 45/166 |
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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 of page ] with values updated to verified values.}} |
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{{cs1 config|name-list-style=vanc|display-authors=6}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457802876 |
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| verifiedrevid = 477240878 |
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| IUPAC_name = Methyl (1''R'',2''R'',4''S'')-4-[(2''R'',5''S'',6''S'')-4-dimethylamino-5-[(2''S'',4''S'',5''S'',6''S'')-4-hydroxy-6-methyl |
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| IUPAC_name = (1''S'',2''S'',4''R'')-Methyl 4-(((2''S'',5''R'',6''R'')-4-(dimethylamino)-5-(((1''S'',3''R'',4''S'')-3-hydroxy-5-methyl-4-(((2''S'',6''R'')-6-methyl-5-oxotetrahydro-2''H''-pyran-2-yl)oxy)cyclohexyl)oxy)-6-methyltetrahydro-2''H''-pyran-2-yl)oxy)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate |
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| image = Aclarubicin.png |
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| image = Aclarubicin.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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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|changed|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 57576-44-0 --> |
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| CAS_number = 57576-44-0 |
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| ATC_prefix = L01 |
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| ATC_prefix = L01 |
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| ATC_suffix = DB04 |
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| ATC_suffix = DB04 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D02756 |
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| KEGG = D02756 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 74619 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 1697719 --> |
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| ChEMBL = 502620 |
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<!--Chemical data--> |
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| C=42 | H=53 | N=1 | O=15 |
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| C=42 | H=53 | N=1 | O=15 |
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| molecular_weight = 811.86 g/mol |
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| smiles = CCC1(CC(C2=C(C1C(=O)OC)C=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O |
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| smiles = CCC1(CC(C2=C(C1C(=O)OC)C=C3C(=C2O)C(=O)C4=C(C3=O)C=CC=C4O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O |
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| InChI = 1/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3 |
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| InChIKey = USZYSDMBJDPRIF-UHFFFAOYAH |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3 |
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| StdInChI = 1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = USZYSDMBJDPRIF-UHFFFAOYSA-N |
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| StdInChIKey = USZYSDMBJDPRIF-UHFFFAOYSA-N |
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| melting_point = 151 |
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| melting_high = 153 |
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| melting_notes = (decomposes) |
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}} |
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}} |
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'''Aclarubicin''' (]) or '''aclacinomycin A'''<ref name="pubchem">{{PubChem|451415}}</ref> is an ] drug<ref name="pmid1655244">{{cite journal | vauthors = Jensen PB, Jensen PS, Demant EJ, Friche E, Sørensen BS, Sehested M, Wassermann K, Vindeløv L, Westergaard O, Hansen HH | title = Antagonistic effect of aclarubicin on daunorubicin-induced cytotoxicity in human small cell lung cancer cells: relationship to DNA integrity and topoisomerase II | journal = Cancer Research | volume = 51 | issue = 19 | pages = 5093–5099 | date = October 1991 | pmid = 1655244 }}</ref> that is used in the treatment of ] in China. It was previously approved for use in Europe but was discontinued in 2004 due to being rarely prescribed and unprofitable. |
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However, it has subsequently been reevaluated<ref>{{cite web | vauthors = Amsen E |title=One man's mission to revive a forgotten, life-saving cancer drug |url=https://www.theguardian.com/science/article/2024/jul/27/one-mans-mission-to-revive-a-forgotten-life-saving-cancer-drug | work = The Guardian |date=27 July 2024}}</ref> due to possible advantages over other chemotherapeutic drugs in the treatment of certain cancers such as ].<ref>{{cite journal | vauthors = Wei G, Ni W, Chiao JW, Cai Z, Huang H, Liu D | title = A meta-analysis of CAG (cytarabine, aclarubicin, G-CSF) regimen for the treatment of 1029 patients with acute myeloid leukemia and myelodysplastic syndrome | journal = Journal of Hematology & Oncology | volume = 4 | pages = 46 | date = November 2011 | pmid = 22082134 | doi = 10.1186/1756-8722-4-46 | doi-access = free | pmc = 3230125 }}</ref><ref>{{cite journal | vauthors = Murzyn A, Orzeł J, Obajtek N, Mróz A, Miodowska D, Bojdo P, Gąsiorkiewicz B, Koczurkiewicz-Adamczyk P, Piska K, Pękala E | title = Aclarubicin: contemporary insights into its mechanism of action, toxicity, pharmacokinetics, and clinical standing | journal = Cancer Chemotherapy and Pharmacology | date = July 2024 | volume = 94 | issue = 2 | pages = 123–139 | pmid = 38965080 | doi = 10.1007/s00280-024-04693-1 | doi-access = free | pmc = 11390774 }}</ref> |
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Soil bacteria '']'' can produce aclarubicin. |
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It can induce ] eviction from ] upon ].<ref name="Pang">{{cite journal | vauthors = Pang B, Qiao X, Janssen L, Velds A, Groothuis T, Kerkhoven R, Nieuwland M, Ovaa H, Rottenberg S, van Tellingen O, Janssen J, Huijgens P, Zwart W, Neefjes J | title = Drug-induced histone eviction from open chromatin contributes to the chemotherapeutic effects of doxorubicin | journal = Nature Communications | volume = 4 | pages = 1908 | year = 2013 | pmid = 23715267 | pmc = 3674280 | doi = 10.1038/ncomms2921 | bibcode = 2013NatCo...4.1908P }}</ref><ref name="pang">{{cite journal | vauthors = Pang B, de Jong J, Qiao X, Wessels LF, Neefjes J | title = Chemical profiling of the genome with anti-cancer drugs defines target specificities | journal = Nature Chemical Biology | volume = 11 | issue = 7 | pages = 472–480 | date = July 2015 | pmid = 25961671 | doi = 10.1038/nchembio.1811 }}</ref> |
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== References == |
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{{reflist}} |
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{{Chemotherapeutic agents}} |
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] |
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] |
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{{antineoplastic-drug-stub}} |