| Revision as of 12:38, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456777225 of page Rebeccamycin for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 21:09, 27 June 2024 edit Attomir (talk | contribs)Extended confirmed users749 editsm wl b16 melanomaTag: 2017 wikitext editor |
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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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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 417954857 |
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| verifiedrevid = 464380411 |
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| IUPAC_name = 1,11-dichloro-12-(4-''O''-methyl-β-<small>D</small>-glucopyranosyl)-12,13-dihydro-5''H''-indolopyrrolocarbazole-5,7(6''H'')-dione |
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| IUPAC_name = 1,11-dichloro-12-(4-''O''-methyl-β-{{small|D}}-glucopyranosyl)-12,13-dihydro-5''H''-indolopyrrolocarbazole-5,7(6''H'')-dione |
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| image = Rebeccamycin.svg |
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| image = Rebeccamycin.svg |
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| width = 190px |
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| width = 190px |
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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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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 93908-02-2 --> |
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| CAS_number = 93908-02-2 |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| PubChem = 73110 |
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| PubChem = 73110 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 65891 |
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| ChemSpiderID = 65891 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 135511 |
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| ChEBI = 135511 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 370100 |
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| ChEMBL = 370100 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = Y96MQM21V9 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=27 | H=21 | Cl=2 | N=3 | O=7 |
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| C=27 | H=21 | Cl=2 | N=3 | O=7 |
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| smiles = CO1(O((1O)O)N2C3=C(C=CC=C3Cl)C4=C5C(=C6C7=C(C(=CC=C7)Cl)NC6=C42)C(=O)NC5=O)CO |
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| molecular_weight = 570.38 |
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| smiles = O=C1c5c(C(=O)N1)c3c2cccc(Cl)c2nc3c6n(c4c(Cl)cccc4c56)7O((OC)(O)7O)CO |
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| InChI = 1/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1 |
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| InChIKey = QEHOIJJIZXRMAN-QZQSLCQPBY |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1 |
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| StdInChI = 1S/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QEHOIJJIZXRMAN-QZQSLCQPSA-N |
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| StdInChIKey = QEHOIJJIZXRMAN-QZQSLCQPSA-N |
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| synonyms = <small>7,10-dichloro-8-(3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2''H''-pyran-2-yl)-8,9-dihydro-1''H''-indolopyrrolocarbazole-1,3(2''H'')-dione</small> |
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| synonyms = {{small|7,10-dichloro-8-(3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2''H''-pyran-2-yl)-8,9-dihydro-1''H''-indolopyrrolocarbazole-1,3(2''H'')-dione}} |
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}} |
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}} |
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'''Rebeccamycin''' ('''NSC 655649''') is a weak ] I inhibitor isolated from '']'' bacteria. It is structurally similar to ], but does not show any inhibitory activity against ]. It shows significant antitumor properties in vitro (IC<sub>50</sub>=480nM against mouse ] cells and IC<sub>50</sub>=500nM against ] leukemia cells). It is an antineoplastic antibiotic and an intercalating agent. |
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Becatecarin (BMS-181176) is a synthetic analog of rebeccamycin.<ref>{{ClinicalTrialsGov|NCT00006017}}</ref> |
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Rebeccamycin and becatecarin have been tested in phase II clinical trials for the treatment of lung cancer, liver cancer, breast cancer, lymphoma, retinoblastoma, kidney cancer, and ovarian cancer.<ref>{{cite web | title = 2 Studies found for: BRN 4732638 | url = https://clinicaltrials.gov/ct2/results?term=BRN+4732638 | work = Clinical Trials Gov }}</ref> |
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== References == |
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{{Reflist}} |
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== Further reading == |
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{{refbegin}} |
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* {{cite journal | vauthors = Nettleton DE, Doyle TW, Krishnan B, Matsumoto GK, Clardy J | title = Isolation and structure of rebeccamycin-a new antitumor antibiotic from Nocardia aerocoligenes. | journal = Tetrahedron Letters | date = January 1985 | volume = 26 | issue = 34 | pages = 4011–4014 | doi = 10.1016/S0040-4039(00)89280-1 }} |
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* {{cite journal | vauthors = Bush JA, Long BH, Catino JJ, Bradner WT, Tomita K | title = Production and biological activity of rebeccamycin, a novel antitumor agent | journal = The Journal of Antibiotics | volume = 40 | issue = 5 | pages = 668–78 | date = May 1987 | pmid = 3112080 | doi = 10.7164/antibiotics.40.668 | doi-access = free }} |
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* {{cite journal | vauthors = Anizon F, Belin L, Moreau P, Sancelme M, Voldoire A, Prudhomme M, Ollier M, Sevère D, Riou JF, Bailly C, Fabbro D, Meyer T | display-authors = 6 | title = Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group | journal = Journal of Medicinal Chemistry | volume = 40 | issue = 21 | pages = 3456–65 | date = October 1997 | pmid = 9341921 | doi = 10.1021/jm9702084 }} |
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* {{cite journal | vauthors = Bailly C, Riou JF, Colson P, Houssier C, Rodrigues-Pereira E, Prudhomme M | title = DNA cleavage by topoisomerase I in the presence of indolocarbazole derivatives of rebeccamycin | journal = Biochemistry | volume = 36 | issue = 13 | pages = 3917–29 | date = April 1997 | pmid = 9092822 | doi = 10.1021/bi9624898 }} |
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* {{cite journal | vauthors = Bailly C, Qu X, Graves DE, Prudhomme M, Chaires JB | title = Calories from carbohydrates: energetic contribution of the carbohydrate moiety of rebeccamycin to DNA binding and the effect of its orientation on topoisomerase I inhibition | journal = Chemistry & Biology | volume = 6 | issue = 5 | pages = 277–86 | date = May 1999 | pmid = 10322124 | doi = 10.1016/S1074-5521(99)80073-8 | doi-access = free }} |
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{{refend}} |
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] |
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{{antineoplastic-drug-stub}} |