Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Plicamycin: Difference between pages

{{short description|Antibiotic}}

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| IUPAC_name = (1''S'')-5-deoxy-1-''C''-((2''S'',3''S'')-7-{[2,6-dideoxy-3-''O''-(2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl)-β-<small>D</small>-''arabino''-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-''C''-methyl-β-<small>D</small>-''ribo''-hexopyranosyl-(1→3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl-(1→3)-2,6-dideoxy-β-<small>D</small>-''arabino''-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-''O''-methyl-<small>D</small>-xylulose

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| pregnancy_US = X

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| legal_US = Rx-only

| legal_status = discontinued

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| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| UNII_Ref = {{fdacite|correct|FDA}}

| KEGG = D00468

| ChEMBL = 509846

<!--Chemical data-->

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'''Plicamycin''' ([[International Nonproprietary Name|INN]], also known as '''mithramycin'''; trade name '''Mithracin''') is an [[antineoplastic]] [[antibiotic]] produced by ''[[Streptomyces plicatus]]''. It is an RNA synthesis inhibitor.<ref>{{cite web |url=http://www.fermentek.com/Mithramycin_A|title=Mithramycin A |publisher=[[Fermentek]]}}</ref> The manufacturer discontinued production in 2000. Several different structures are currently reported in different places all with the same chromomycin core, but with different stereochemistry in the glycoside chain, a 1999 study has re-investigated the compound and proposed a revised structure.<ref>{{cite journal | vauthors = Wohlert SE, Künzel E, Machinek R, Méndez C, Salas JA, Rohr J | title = The structure of mithramycin reinvestigated | journal = Journal of Natural Products | volume = 62 | issue = 1 | pages = 119–121 | date = January 1999 | pmid = 9917296 | doi = 10.1021/np980355k }}</ref>

==Uses==

Plicamycin has been used in the treatment of [[testicular cancer]],<ref name="pmid7700186">{{cite journal | vauthors = Kennedy BJ, Torkelson JL | title = Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin) | journal = Medical and Pediatric Oncology | volume = 24 | issue = 5 | pages = 327–328 | date = May 1995 | pmid = 7700186 | doi = 10.1002/mpo.2950240511 }}</ref><ref>{{cite journal | vauthors = Brown JH, Kennedy BJ | title = Mithramycin in the Treatment of Disseminated Testicular Neoplasms | journal = The New England Journal of Medicine | volume = 272 | issue = 3 | pages = 111–118 | date = January 1965 | pmid = 14224214 | doi = 10.1056/NEJM196501212720301 }}</ref> [[Paget's disease of bone]],<ref>{{cite journal | vauthors = Hall TJ, Schaeublin M, Chambers TJ | title = The majority of osteoclasts require mRNA and protein synthesis for bone resorption in vitro | journal = Biochemical and Biophysical Research Communications | volume = 195 | issue = 3 | pages = 1245–1253 | date = September 1993 | pmid = 8216256 | doi = 10.1006/bbrc.1993.2178 }}</ref><ref>{{cite journal | vauthors = Remsing LL, Bahadori HR, Carbone GM, McGuffie EM, Catapano CV, Rohr J | title = Inhibition of c-src transcription by mithramycin: structure-activity relationships of biosynthetically produced mithramycin analogues using the c-src promoter as target | journal = Biochemistry | volume = 42 | issue = 27 | pages = 8313–8324 | date = July 2003 | pmid = 12846580 | doi = 10.1021/bi034091z }}</ref> and, rarely, the management of [[hypercalcemia]].

Plicamycin has been tested in [[chronic myeloid leukemia]].<ref name="pmid9225062">{{cite journal | vauthors = Dutcher JP, Coletti D, Paietta E, Wiernik PH | title = A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia | journal = Leukemia Research | volume = 21 | issue = 5 | pages = 375–380 | date = May 1997 | pmid = 9225062 | doi = 10.1016/S0145-2126(96)00108-7 }}</ref>

Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis<ref>{{cite journal | vauthors = Lee TJ, Jung EM, Lee JT, Kim S, Park JW, Choi KS, Kwon TK | title = Mithramycin A sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites | journal = Molecular Cancer Therapeutics | volume = 5 | issue = 11 | pages = 2737–2746 | date = November 2006 | pmid = 17121920 | doi = 10.1158/1535-7163.MCT-06-0426 | doi-access = free }}</ref> and as a metastasis inhibitor.<ref>{{cite journal | vauthors = Lin RK, Hsu CH, Wang YC | title = Mithramycin A inhibits DNA methyltransferase and metastasis potential of lung cancer cells | journal = Anti-Cancer Drugs | volume = 18 | issue = 10 | pages = 1157–1164 | date = November 2007 | pmid = 17893516 | doi = 10.1097/CAD.0b013e3282a215e9 }}</ref>

One elucidated pathway shows it interacts by cross-binding [[chromatin]] GC-rich promoter motifs, thereby inhibiting [[gene transcription]].<ref>{{cite journal | vauthors = Majee S, Chakrabarti A | title = Membrane interaction of an antitumor antibiotic, mithramycin, with anionic phospholipid vesicles | journal = Biochemical Pharmacology | volume = 57 | issue = 9 | pages = 981–987 | date = May 1999 | pmid = 10796068 | doi = 10.1016/S0006-2952(98)00374-8 }}</ref>

== References ==

{{reflist}}

== External links ==

*[https://web.archive.org/web/20151122093256/http://pharmacy.mc.uky.edu/cpri/snpa.php Mithramycin A from ] [[Center for Pharmaceutical Research and Innovation]]

{{Chemotherapeutic agents}}

{{Xenobiotic-sensing receptor modulators}}

[[Category:DNA replication inhibitors]]