plicamycin

Also known as PA-144, A-2371, Mithracin, Mithramycinum, Plicamycinum, Mithramycin, Plicamycine, Mithramycine

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.

In the Vinony graph

Within Vinony's link graph, plicamycin is referenced by 438 other articles, and connects out to epothilones, tiazofurin and antibiotic.

It sits within the topics DNA replication inhibitors, Drugboxes which contain changes to verified fields and Drugs with non-standard legal status.

Its subject is documented across 10 Wikipedia language editions.

Chemical data

Formula: C52H76O24
Molecular weight: 1085.1 g/mol
IUPAC name: (2S,3S)-2-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4-[(2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-6-[(2S,4R,5R,6R)-4-[(2S,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5-hydroxy-6-methyloxan-2-yl]oxy-8,9-dihydroxy-7-methyl-3,4-dihydro-2H-anthracen-1-one
SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2C[C@@H](O[C@@H]([C@H]2O)C)OC3=CC4=CC5=C(C(=O)[C@H]([C@@H](C5)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)O)O[C@H]7C[C@H]([C@H]([C@H](O7)C)O)O[C@H]8C[C@]([C@@H]([C@H](O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O
InChIKey: CFCUWKMKBJTWLW-BKHRDMLASA-N
XLogP: 0.6
Polar surface area: 358 Å²
H-bond donors: 11
H-bond acceptors: 24
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1970
Admin. routes: parenteral
Indications: neoplasm, Ewing sarcoma, sarcoma

via ChEMBL · EBI

Research

1,047 papers

Macrophage-organoid co-culture model for identifying treatment strategies against macrophage-related gemcitabine resistance.Journal of experimental & clinical cancer research : CR · 2023
Everolimus and plicamycin specifically target chemoresistant colorectal cancer cells of the CMS4 subtype.Cell death & disease · 2021
Plicamycin: bolus or infusion?DICP : the annals of pharmacotherapy · 1990
Plicamycin and pamidronate in symptomatic tumor-related hypercalcemia: a prospective randomized crossover trial.Annals of oncology : official journal of the European Society for Medical Oncology · 1992
Determination of plicamycin in plasma by radioimmunoassay.Therapeutic drug monitoring · 1992

via PubMed

Wikidata facts

Mass: 1084.472653
Has use: medication

Show 5 more facts

chemical formula: C₅₂H₇₆O₂₄
medical condition treated: hypercalcemia
canonical SMILES: CC1C(C(CC(O1)OC2CC(OC(C2O)C)OC3=CC4=CC5=C(C(=O)C(C(C5)C(C(=O)C(C(C)O)O)OC)OC6CC(C(C(O6)C)O)OC7CC(C(C(O7)C)OC8CC(C(C(O8)C)O)(C)O)O)C(=C4C(=C3C)O)O)O)O
isomeric SMILES: C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2C[C@@H](O[C@@H]([C@H]2O)C)OC3=CC4=CC5=C(C(=O)[C@H]([C@@H](C5)[C@@H](C(=O)[C@H]([C@@H](C)O)O)OC)O[C@H]6C[C@H]([C@@H]([C@H](O6)C)O)O[C@H]7C[C@H]([C@H]([C@H](O7)C)O)O[C@H]8C[C@]([C@@H]([C@H](O8)C)O)(C)O)C(=C4C(=C3C)O)O)O)O
subject has role: protein synthesis inhibitor

Sources (3)

via Wikidata · CC0

~3 min read

Encyclopedic overview

3 sections

Contents

Uses
References
External links

{{Drugbox | 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

Excerpted from Wikipedia’s “plicamycin” article, available under the CC BY-SA 4.0 licence.