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Revision as of 13:26, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{drugbox}} taken from revid 456592644 of page Plicamycin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'KEGG').  Latest revision as of 07:42, 9 July 2023 edit Boghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,879 edits consistent citation formatting 
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{{short description|Antibiotic}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
⚫ | verifiedrevid = 464208709
| Watchedfields = changed
⚫ | IUPAC_name = (1''S'')-5-deoxy-1-''C''-((2''S'',3''S'')-7-{oxy}-3-{oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-''O''-methyl-<small>D</small>-xylulose
⚫ | verifiedrevid = 400856269
⚫ | IUPAC_name = (1''S'')-5-deoxy-1-''C''-((2''S'',3''S'')-7-{oxy}-3-{oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-''O''-methyl-<small>D</small>-xylulose
| image = Plicamycin.svg | image = Plicamycin.svg
| width = 300


<!--Clinical data--> <!--Clinical data-->
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| Drugs.com = {{drugs.com|CONS|plicamycin}} | Drugs.com = {{drugs.com|CONS|plicamycin}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = X
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C --> | legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US = Rx-only
| legal_status = | legal_status = discontinued
| routes_of_administration = ] | routes_of_administration = ]


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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
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| ATC_suffix = DC02 | ATC_suffix = DC02
| PubChem = 5284610 | PubChem = 5284610
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB06810 | DrugBank = DB06810
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4447655 | ChemSpiderID = 4447655
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = NIJ123W41V | UNII = NIJ123W41V
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = <!-- blanked - oldvalue: D00468 --> | KEGG = D00468
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 509846 --> | ChEMBL = 509846

<!--Chemical data-->
| C=52 | H=76 | O=24 | C=52 | H=76 | O=24
| smiles = CO(C(=O)(O)(C)O)C1Cc2cc3cc(O4C(O5C(O)(O)(C)O5)(O)(C)O4)c(C)c(O)c3c(O)c2C(=O)1O1C(O2C(O3C(C)(O)(O)(C)O3)(O)(C)O2)(O)(C)O1
| molecular_weight = 1085.15 g/mol
| InChI = 1/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27?,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1
| InChIKey = CFCUWKMKBJTWLW-GWRQQDNDBX
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27?,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1 | StdInChI = 1S/C52H76O24/c1-18-29(72-34-14-30(43(58)21(4)68-34)73-33-13-28(54)42(57)20(3)67-33)12-26-10-25-11-27(49(66-9)48(63)41(56)19(2)53)50(47(62)39(25)46(61)38(26)40(18)55)76-36-16-31(44(59)23(6)70-36)74-35-15-32(45(60)22(5)69-35)75-37-17-52(8,65)51(64)24(7)71-37/h10,12,19-24,27-28,30-37,41-45,49-51,53-61,64-65H,11,13-17H2,1-9H3/t19-,20-,21-,22-,23-,24-,27?,28-,30-,31-,32-,33+,34+,35+,36+,37+,41+,42-,43+,44-,45-,49+,50+,51-,52+/m1/s1
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| synonyms = Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin | synonyms = Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin
}} }}

'''Plicamycin''' (], also known as '''mithramycin'''; trade name '''Mithracin''') is an ] ] produced by '']''. It is an RNA synthesis inhibitor.<ref>{{cite web |url=http://www.fermentek.com/Mithramycin_A|title=Mithramycin A |publisher=]}}</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 ],<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> ],<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 ].

Plicamycin has been tested in ].<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 ] GC-rich promoter motifs, thereby inhibiting ].<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 ==
* ]

{{Chemotherapeutic agents}}
{{Xenobiotic-sensing receptor modulators}}

]
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