Plicamycin

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Antibiotic

title: "Plicamycin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["dna-replication-inhibitors"] description: "Antibiotic" topic_path: "general/dna-replication-inhibitors" source: "https://en.wikipedia.org/wiki/Plicamycin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Antibiotic ::

| Verifiedfields = changed | verifiedrevid = 464208709 | IUPAC_name = (1S)-5-deoxy-1-C-((2S,3S)-7-{[2,6-dideoxy-3-O-(2,6-dideoxy-β-D-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl]oxy}-3-{[2,6-dideoxy-3-C-methyl-β-D-ribo-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1→3)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy}-5,10-dihydroxy-6-methyl-4-oxo-1,2,3,4-tetrahydroanthracen-2-yl)-1-O-methyl-D-xylulose | image = Plicamycin.svg | image_class = skin-invert-image | width = 300

| tradename = | Drugs.com = | pregnancy_AU = | pregnancy_US = X | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = Rx-only | legal_status = discontinued | routes_of_administration = Intravenous

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 18378-89-7 | ATC_prefix = L01 | ATC_suffix = DC02 | PubChem = 5284610 | DrugBank_Ref = | DrugBank = DB06810 | ChemSpiderID_Ref = | ChemSpiderID = 4447655 | ChEBI = 31856 | UNII_Ref = | UNII = NIJ123W41V | KEGG_Ref = | KEGG = D00468 | ChEMBL_Ref = | ChEMBL = 509846

| C=52 | H=76 | O=24 | smiles = COC@HC1Cc2cc3cc(O[C@H]4CC@@HC@@HC@@HO4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]1CC@@HC@HC@@HO1 | StdInChI_Ref = | 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 | StdInChIKey_Ref = | StdInChIKey = CFCUWKMKBJTWLW-GWRQQDNDSA-N | synonyms = Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin

Plicamycin (INN, also known as mithramycin; trade name Mithracin) is an antineoplastic antibiotic produced by Streptomyces plicatus. It is an RNA synthesis inhibitor. 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.

Uses

Plicamycin has been used in the treatment of testicular cancer, Paget's disease of bone, and, rarely, the management of hypercalcemia.

Plicamycin has been tested in chronic myeloid leukemia.

Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis and as a metastasis inhibitor.

One elucidated pathway shows it interacts by cross-binding chromatin GC-rich promoter motifs, thereby inhibiting gene transcription.

References

References

  1. (January 2004). "Mithramycin A". [[Fermentek]].
  2. (January 1999). "The structure of mithramycin reinvestigated". Journal of Natural Products.
  3. (May 1995). "Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin)". Medical and Pediatric Oncology.
  4. (January 1965). "Mithramycin in the Treatment of Disseminated Testicular Neoplasms". The New England Journal of Medicine.
  5. (September 1993). "The majority of osteoclasts require mRNA and protein synthesis for bone resorption in vitro". Biochemical and Biophysical Research Communications.
  6. (July 2003). "Inhibition of c-src transcription by mithramycin: structure-activity relationships of biosynthetically produced mithramycin analogues using the c-src promoter as target". Biochemistry.
  7. (May 1997). "A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia". Leukemia Research.
  8. (November 2006). "Mithramycin A sensitizes cancer cells to TRAIL-mediated apoptosis by down-regulation of XIAP gene promoter through Sp1 sites". Molecular Cancer Therapeutics.
  9. (November 2007). "Mithramycin A inhibits DNA methyltransferase and metastasis potential of lung cancer cells". Anti-Cancer Drugs.
  10. (May 1999). "Membrane interaction of an antitumor antibiotic, mithramycin, with anionic phospholipid vesicles". Biochemical Pharmacology.

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dna-replication-inhibitors