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Details

Stereochemistry ABSOLUTE
Molecular Formula C52H76O24
Molecular Weight 1085.1454
Optical Activity UNSPECIFIED
Defined Stereocenters 25 / 25
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Plicamycin

SMILES

CO[C@@H]([C@@H]1CC2=C(C(=O)[C@H]1O[C@H]3C[C@@H](O[C@H]4C[C@@H](O[C@H]5C[C@](C)(O)[C@H](O)[C@@H](C)O5)[C@@H](O)[C@@H](C)O4)[C@H](O)[C@@H](C)O3)C(O)=C6C(C=C(O[C@H]7C[C@@H](O[C@H]8C[C@@H](O)[C@H](O)[C@@H](C)O8)[C@H](O)[C@@H](C)O7)C(C)=C6O)=C2)C(=O)[C@@H](O)[C@@H](C)O

InChI

InChIKey=CFCUWKMKBJTWLW-BKHRDMLASA-N
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

HIDE SMILES / InChI

Description

Plicamycin (INN, also known as mithramycin; trade name Mithracin) is an antineoplastic antibiotic produced by Streptomyces plicatus. Plicamycin belongs to the group of medicines known as antineoplastics. It may be used to treat certain types of cancer. It is also used to treat hypercalcemia or hypercalciuria (too much calcium in the blood or urine) that may occur with some types of cancer. Once a medicine has been approved for marketing for a certain use, experience may show that it is also useful for other medical problems. Although this use is not included in product labeling, plicamycin is used in certain patients with the following medical condition:Paget's disease of the bone. The manufacturer discontinued plicamycin 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. Although the exact mechanism by which Mithracin (plicamycin) causes tumor inhibition is not yet known, studies have indicated that this compound forms a complex with deoxyribonucleic acid (DNA) and inhibits cellular ribonucleic acid (RNA) and enzymic RNA synthesis. The binding of Mithracin (plicamycin) to DNA in the presence of Mg + + (or other divalent cations) is responsible for the inhibition of DNA-dependent or DNA-directed RNA synthesis. This action presumably accounts for the biological properties of Mithracin (plicamycin). Plicamycin may also lower calcium serum levels by inhibiting the effect of parathyroid hormone upon osteoclasts or by blocking the hypercalcemic action of pharmacologic doses of vitamin D.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
400.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MITHRACIN
Secondary
MITHRACIN

Cmax

ValueDoseCo-administeredAnalytePopulation
350 ng/mL
1 mg/m² single, intravenous
PLICAMYCIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1489 ng × h/mL
1 mg/m² single, intravenous
PLICAMYCIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
10.6 h
1 mg/m² single, intravenous
PLICAMYCIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
15-25 ug/kg bw
Route of Administration: Intravenous
In Vitro Use Guide
Unknown