Plicamycin

Plicamycin (INN, also known as mithramycin; trade name Mithracin) is an antineoplastic antibiotic produced by Streptomyces plicatus. It is an RNA synthesis inhibitor.^[1] 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.^[2]

Plicamycin

Clinical data
Other names	Aureolic acid; Mithracin; Antibiotic LA 7017; Mithramycin A; Mitramycin; Plicatomycin
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Intravenous
ATC code	L01DC02 (WHO)
Legal status
Legal status	US: ℞-only discontinued
Identifiers
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
CAS Number	18378-89-7 Y
PubChem CID	5284610
DrugBank	DB06810 Y
ChemSpider	4447655 Y
UNII	NIJ123W41V
KEGG	D00468 N
ChEMBL	ChEMBL509846 N
CompTox Dashboard (EPA)	DTXSID6023492
ECHA InfoCard	100.162.065
Chemical and physical data
Formula	C52H76O24
Molar mass	1085.156 g·mol−1
3D model (JSmol)	Interactive image
SMILES CO[C@H](C(=O)[C@@H](O)[C@@H](C)O)C1Cc2cc3cc(O[C@H]4C[C@@H](O[C@H]5C[C@@H](O)[C@H](O)[C@@H](C)O5)[C@@H](O)[C@@H](C)O4)c(C)c(O)c3c(O)c2C(=O)[C@H]1O[C@H]1C[C@@H](O[C@H]2C[C@@H](O[C@H]3C[C@](C)(O)[C@H](O)[C@@H](C)O3)[C@H](O)[C@@H](C)O2)[C@H](O)[C@@H](C)O1
InChI InChI=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 Y Key:CFCUWKMKBJTWLW-GWRQQDNDSA-N Y
NY (what is this?)  (verify)

Uses

Plicamycin has been used in the treatment of testicular cancer,^[3][4] Paget's disease of bone,^[5][6] and, rarely, the management of hypercalcemia.

Plicamycin has been tested in chronic myeloid leukemia.^[7]

Plicamycin is currently used in multiple areas of research, including cancer cell apoptosis^[8] and as a metastasis inhibitor.^[9]

One elucidated pathway shows it interacts by cross-binding chromatin GC-rich promoter motifs, thereby inhibiting gene transcription.^[10]