Identification

Name
Plicamycin
Accession Number
DB06810
Type
Small Molecule
Groups
Approved, Investigational, Withdrawn
Description

Plicamycin is an antineoplastic antibiotic produced by Streptomyces plicatus. It has been used in the treatment of testicular cancer, Paget's disease of bone, and, rarely, the management of hypercalcemia. The manufacturer discontinued plicamycin in 2000.

Structure
Thumb
Synonyms
  • Aureolic acid
  • Mithramycin
  • Mithramycine
  • Mithramycinum
  • Plicamycin
  • Plicamycine
  • Plicamycinum
External IDs
A-2371 / ANTIBIOTIC LA-7017 / LA-7017 / NSC-24559 / PA-144
International/Other Brands
Mithracin (Pfizer)
Categories
UNII
NIJ123W41V
CAS number
18378-89-7
Weight
Average: 1085.1454
Monoisotopic: 1084.47265336
Chemical Formula
C52H76O24
InChI Key
CFCUWKMKBJTWLW-BKHRDMLASA-N
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
IUPAC Name
(2S,3S)-3-[(1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl]-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}-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-1,2,3,4-tetrahydroanthracen-1-one
SMILES

Pharmacology

Indication

For the treatment of testicular cancer, as well as hypercalcemia and hypercalciuria associated with a variety of advanced forms of cancer.

Structured Indications
Not Available
Pharmacodynamics

Plicamycin is lethal to Hela cells in 48 hours at concentrations as low as 0.5 micrograms per milliliter of tissue culture medium. Plicamycin has shown significant anti-tumor activity against experimental leukemia in mice when administered intraperitoneally.

Mechanism of action

Plicamycin is presumed to inhibit cellular and enzymic RNA synthesis by forming a complex with DNA. 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.

TargetActionsOrganism
ADNA
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

There is no evidence of protein binding, nor is there any evidence of metabolism of the carbohydrate moiety of the drug to carbon dioxide and water with loss through respiration.

Metabolism
Not Available
Route of elimination

Radioautography studies with 3H-labeled plicamycin in mice show that the greatest concentrations of the isotope are in the Kupffer cells of the liver and cells of the renal tubules. Plicamycin is rapidly cleared from the blood within the first 2 hours and excretion is also rapid. 67% percent of measured excretion occurs within 4 hours, 75% within 8 hours, and 90% is recovered in the first 24 hours after injection.

Half life
Not Available
Clearance
Not Available
Toxicity

The most important form of toxicity associated with the use of plicamycin consists of a dose-related bleeding syndrome which usually begins with an episode of epistaxis. Plicamycin crosses the blood-brain barrier; the concentration found in brain tissue is low but it persists longer than in other tissues.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AceclofenacAceclofenac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
AcemetacinAcemetacin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Plicamycin.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Plicamycin.Experimental
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
AdapaleneAdapalene may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
AlclofenacAlclofenac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Withdrawn
AlcuroniumPlicamycin may increase the respiratory depressant activities of Alcuronium.Experimental
Alendronic acidPlicamycin may increase the hypocalcemic activities of Alendronic acid.Approved
AlminoprofenAlminoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
AmdinocillinThe serum concentration of Plicamycin can be decreased when it is combined with Amdinocillin.Investigational, Withdrawn
AmoxicillinThe serum concentration of Plicamycin can be decreased when it is combined with Amoxicillin.Approved, Vet Approved
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Plicamycin.Approved, Investigational
AmpicillinThe serum concentration of Plicamycin can be decreased when it is combined with Ampicillin.Approved, Vet Approved
AndrographolideAndrographolide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
AnisodamineAnisodamine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
AntipyrineAntipyrine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
ApocyninApocynin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
ApremilastApremilast may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
AspoxicillinThe serum concentration of Plicamycin can be decreased when it is combined with Aspoxicillin.Experimental
AtracuriumPlicamycin may increase the respiratory depressant activities of Atracurium.Experimental, Investigational
Atracurium besylatePlicamycin may increase the respiratory depressant activities of Atracurium besylate.Approved
AzapropazoneAzapropazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Withdrawn
AzelastineAzelastine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
AzidocillinThe serum concentration of Plicamycin can be decreased when it is combined with Azidocillin.Approved
AzlocillinThe serum concentration of Plicamycin can be decreased when it is combined with Azlocillin.Approved
BacampicillinThe serum concentration of Plicamycin can be decreased when it is combined with Bacampicillin.Approved, Investigational
BalsalazideBalsalazide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
BendazacBendazac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
BenorilateBenorilate may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
BenoxaprofenBenoxaprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Withdrawn
Benzathine benzylpenicillinThe serum concentration of Plicamycin can be decreased when it is combined with Benzathine benzylpenicillin.Approved, Vet Approved
BenzylpenicillinThe serum concentration of Plicamycin can be decreased when it is combined with Benzylpenicillin.Approved, Vet Approved
Benzylpenicilloyl PolylysineThe serum concentration of Plicamycin can be decreased when it is combined with Benzylpenicilloyl Polylysine.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Plicamycin.Approved, Investigational
BevoniumBevonium may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
Botulinum Toxin Type APlicamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.Approved, Investigational
Botulinum Toxin Type BPlicamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.Approved
BromfenacBromfenac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
BucillamineBucillamine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
BufexamacBufexamac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
BumadizoneBumadizone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Plicamycin.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Plicamycin.Approved
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Plicamycin.Approved
Carbaspirin calciumCarbaspirin calcium may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental, Investigational
CarbenicillinThe serum concentration of Plicamycin can be decreased when it is combined with Carbenicillin.Approved, Investigational
Carbenicillin indanylThe serum concentration of Plicamycin can be decreased when it is combined with Carbenicillin indanyl.Approved, Investigational
CarboplatinPlicamycin may increase the ototoxic activities of Carboplatin.Approved
CarfecillinThe serum concentration of Plicamycin can be decreased when it is combined with Carfecillin.Experimental
CarprofenCarprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved, Withdrawn
CastanospermineCastanospermine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
CelecoxibCelecoxib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
ChloroquineChloroquine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
Choline magnesium trisalicylateCholine magnesium trisalicylate may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
CisatracuriumPlicamycin may increase the respiratory depressant activities of Cisatracurium.Approved, Experimental
Cisatracurium besylatePlicamycin may increase the respiratory depressant activities of Cisatracurium besylate.Approved
CisplatinCisplatin may increase the nephrotoxic activities of Plicamycin.Approved
Clodronic AcidPlicamycin may increase the hypocalcemic activities of Clodronic Acid.Approved, Investigational, Vet Approved
ClonixinClonixin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
CloxacillinThe serum concentration of Plicamycin can be decreased when it is combined with Cloxacillin.Approved, Vet Approved
ColistimethatePlicamycin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
CurcuminCurcumin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
CyclacillinThe serum concentration of Plicamycin can be decreased when it is combined with Cyclacillin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Plicamycin.Approved, Investigational
CyclosporinePlicamycin may increase the nephrotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Plicamycin.Experimental
D-LimoneneD-Limonene may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
DecamethoniumPlicamycin may increase the respiratory depressant activities of Decamethonium.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Plicamycin.Approved
DiclofenacDiclofenac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
DicloxacillinThe serum concentration of Plicamycin can be decreased when it is combined with Dicloxacillin.Approved, Vet Approved
DifenpiramideDifenpiramide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
DiflunisalDiflunisal may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Plicamycin.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Plicamycin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Plicamycin.Approved, Investigational
Domoic AcidPlicamycin may increase the respiratory depressant activities of Domoic Acid.Experimental
Doxacurium chloridePlicamycin may increase the respiratory depressant activities of Doxacurium chloride.Approved
DroxicamDroxicam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
DuvelisibDuvelisib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
E-6201E-6201 may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
EpicillinThe serum concentration of Plicamycin can be decreased when it is combined with Epicillin.Experimental
EpirizoleEpirizole may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Plicamycin.Approved
EtanerceptEtanercept may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
EthenzamideEthenzamide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
Etidronic acidPlicamycin may increase the hypocalcemic activities of Etidronic acid.Approved
EtodolacEtodolac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
EtoricoxibEtoricoxib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
Evening primrose oilEvening primrose oil may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
exisulindexisulind may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
FelbinacFelbinac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
FenbufenFenbufen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
FenoprofenFenoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
FentiazacFentiazac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
FeprazoneFeprazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
Ferulic acidFerulic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
FloctafenineFloctafenine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Withdrawn
FlucloxacillinThe serum concentration of Plicamycin can be decreased when it is combined with Flucloxacillin.Approved, Investigational
FlunixinFlunixin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Vet Approved
FlunoxaprofenFlunoxaprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
FlurbiprofenFlurbiprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
FoscarnetFoscarnet may increase the nephrotoxic activities of Plicamycin.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Plicamycin.Approved, Vet Approved
GallaminePlicamycin may increase the respiratory depressant activities of Gallamine.Experimental
Gallamine TriethiodidePlicamycin may increase the respiratory depressant activities of Gallamine Triethiodide.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Plicamycin.Experimental
GuacetisalGuacetisal may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
HigenamineHigenamine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
IbandronatePlicamycin may increase the hypocalcemic activities of Ibandronate.Approved, Investigational
IbuprofenIbuprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
IbuproxamIbuproxam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Withdrawn
IcatibantIcatibant may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
Imidazole salicylateImidazole salicylate may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
IndobufenIndobufen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
IndomethacinIndomethacin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
IndoprofenIndoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Withdrawn
IsoxicamIsoxicam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Withdrawn
KebuzoneKebuzone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
KetoprofenKetoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
KetorolacKetorolac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Plicamycin.Experimental
LeflunomideLeflunomide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
LisofyllineLisofylline may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
LonazolacLonazolac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
LornoxicamLornoxicam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
LoxoprofenLoxoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
LumiracoxibLumiracoxib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
MannitolMannitol may increase the nephrotoxic activities of Plicamycin.Approved, Investigational
MasoprocolMasoprocol may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
MecamylaminePlicamycin may increase the neuromuscular blocking activities of Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
MeloxicamMeloxicam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
MesalazineMesalazine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
MetamizoleMetamizole may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational, Withdrawn
MetampicillinThe serum concentration of Plicamycin can be decreased when it is combined with Metampicillin.Experimental
MeticillinThe serum concentration of Plicamycin can be decreased when it is combined with Meticillin.Approved, Investigational
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Plicamycin.Experimental
MetocurinePlicamycin may increase the respiratory depressant activities of Metocurine.Approved
Metocurine IodidePlicamycin may increase the respiratory depressant activities of Metocurine Iodide.Withdrawn
MezlocillinThe serum concentration of Plicamycin can be decreased when it is combined with Mezlocillin.Approved, Investigational
MivacuriumPlicamycin may increase the respiratory depressant activities of Mivacurium.Approved
MizoribineMizoribine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
MofebutazoneMofebutazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
Mycophenolate mofetilMycophenolate mofetil may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
NabumetoneNabumetone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
NafamostatNafamostat may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
NafcillinThe serum concentration of Plicamycin can be decreased when it is combined with Nafcillin.Approved
NaftifineNaftifine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
NaproxenNaproxen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
NeosaxitoxinPlicamycin may increase the respiratory depressant activities of Neosaxitoxin.Investigational
NepafenacNepafenac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
NifenazoneNifenazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
Niflumic AcidNiflumic Acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
NimesulideNimesulide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational, Withdrawn
NitroaspirinNitroaspirin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Plicamycin.Experimental, Investigational
OlopatadineOlopatadine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
OlsalazineOlsalazine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
OrgoteinOrgotein may decrease the excretion rate of Plicamycin which could result in a higher serum level.Vet Approved
OuabainOuabain may decrease the cardiotoxic activities of Plicamycin.Approved
OxacillinThe serum concentration of Plicamycin can be decreased when it is combined with Oxacillin.Approved
OxaprozinOxaprozin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
OxyphenbutazoneOxyphenbutazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Plicamycin.Approved, Vet Approved
PamidronatePlicamycin may increase the hypocalcemic activities of Pamidronate.Approved
PancuroniumPlicamycin may increase the respiratory depressant activities of Pancuronium.Approved
ParecoxibParecoxib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
ParthenolideParthenolide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
PenamecillinThe serum concentration of Plicamycin can be decreased when it is combined with Penamecillin.Experimental
PenimepicyclineThe serum concentration of Plicamycin can be decreased when it is combined with Penimepicycline.Experimental
PeruvosidePeruvoside may decrease the cardiotoxic activities of Plicamycin.Experimental
PhenoxymethylpenicillinThe serum concentration of Plicamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
PhenylbutazonePhenylbutazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
PimecrolimusPimecrolimus may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
PipecuroniumPlicamycin may increase the respiratory depressant activities of Pipecuronium.Approved
PiperacillinThe serum concentration of Plicamycin can be decreased when it is combined with Piperacillin.Approved
PiretanideThe risk or severity of adverse effects can be increased when Piretanide is combined with Plicamycin.Experimental
PirfenidonePirfenidone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
PiroxicamPiroxicam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
PirprofenPirprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
PivampicillinThe serum concentration of Plicamycin can be decreased when it is combined with Pivampicillin.Approved
PivmecillinamThe serum concentration of Plicamycin can be decreased when it is combined with Pivmecillinam.Approved
PranoprofenPranoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental, Investigational
Procaine benzylpenicillinThe serum concentration of Plicamycin can be decreased when it is combined with Procaine benzylpenicillin.Approved, Vet Approved
ProglumetacinProglumetacin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
PropacetamolPropacetamol may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
PropicillinThe serum concentration of Plicamycin can be decreased when it is combined with Propicillin.Experimental
PropyphenazonePropyphenazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
ProquazoneProquazone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Plicamycin.Experimental
PTC299PTC299 may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
PyrantelPlicamycin may increase the respiratory depressant activities of Pyrantel.Approved, Vet Approved
RapacuroniumPlicamycin may increase the respiratory depressant activities of Rapacuronium.Withdrawn
ResveratrolResveratrol may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Experimental, Investigational
RisedronatePlicamycin may increase the hypocalcemic activities of Risedronate.Approved, Investigational
RocuroniumPlicamycin may increase the respiratory depressant activities of Rocuronium.Approved
RofecoxibRofecoxib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational, Withdrawn
SalicylamideSalicylamide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
Salicylic acidSalicylic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Vet Approved
SalsalateSalsalate may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
SemapimodSemapimod may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
SeratrodastSeratrodast may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
SerrapeptaseSerrapeptase may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
SRT501SRT501 may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
SuccinylcholinePlicamycin may increase the respiratory depressant activities of Succinylcholine.Approved
SulbactamThe serum concentration of Plicamycin can be decreased when it is combined with Sulbactam.Approved
SulbenicillinThe serum concentration of Plicamycin can be decreased when it is combined with Sulbenicillin.Experimental
SulfasalazineSulfasalazine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
SulindacSulindac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
SultamicillinThe serum concentration of Plicamycin can be decreased when it is combined with Sultamicillin.Investigational
SuprofenSuprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Withdrawn
SuxibuzoneSuxibuzone may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
TalampicillinThe serum concentration of Plicamycin can be decreased when it is combined with Talampicillin.Experimental
TarenflurbilTarenflurbil may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
TazobactamThe serum concentration of Plicamycin can be decreased when it is combined with Tazobactam.Approved
Technetium Tc-99m etidronatePlicamycin may increase the hypocalcemic activities of Technetium Tc-99m etidronate.Approved
Technetium Tc-99m medronatePlicamycin may increase the hypocalcemic activities of Technetium Tc-99m medronate.Approved
TenidapTenidap may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
Tenofovir disoproxilThe serum concentration of Plicamycin can be increased when it is combined with Tenofovir disoproxil.Approved, Investigational
TenoxicamTenoxicam may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
TepoxalinTepoxalin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Vet Approved
TeriflunomideTeriflunomide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
TicarcillinThe serum concentration of Plicamycin can be decreased when it is combined with Ticarcillin.Approved, Investigational, Vet Approved
Tiludronic acidPlicamycin may increase the hypocalcemic activities of Tiludronic acid.Approved, Investigational, Vet Approved
TinoridineTinoridine may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
Tolfenamic AcidTolfenamic Acid may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
TolmetinTolmetin may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Plicamycin.Approved
TranilastTranilast may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Plicamycin.Approved, Investigational
TribenosideTribenoside may decrease the excretion rate of Plicamycin which could result in a higher serum level.Experimental
TriptolideTriptolide may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational
TubocurarinePlicamycin may increase the respiratory depressant activities of Tubocurarine.Approved
ValdecoxibValdecoxib may decrease the excretion rate of Plicamycin which could result in a higher serum level.Investigational, Withdrawn
VancomycinVancomycin may increase the nephrotoxic activities of Plicamycin.Approved
VecuroniumPlicamycin may increase the respiratory depressant activities of Vecuronium.Approved
ZaltoprofenZaltoprofen may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational
ZileutonZileuton may decrease the excretion rate of Plicamycin which could result in a higher serum level.Approved, Investigational, Withdrawn
Zoledronic acidPlicamycin may increase the hypocalcemic activities of Zoledronic acid.Approved
ZomepiracZomepirac may decrease the excretion rate of Plicamycin which could result in a higher serum level.Withdrawn
Food Interactions
Not Available

References

Synthesis Reference

Jurgen Rohr, Lily Remsing, Mohammad Nur-e-Alam, Jose Salas, Carmen Mendez, Alfredo Brana, Ana Gonzalez, "Derivatives of mithramycin and methods of making and uses thereof." U.S. Patent US20050192432, issued September 01, 2005.

US20050192432
General References
  1. Wohlert SE, Kunzel E, Machinek R, Mendez C, Salas JA, Rohr J: The structure of mithramycin reinvestigated. J Nat Prod. 1999 Jan;62(1):119-21. [PubMed:9917296]
External Links
Human Metabolome Database
HMDB15682
KEGG Drug
D00468
KEGG Compound
C12389
PubChem Compound
163659
PubChem Substance
99443298
ChemSpider
143544
ChEBI
31856
ChEMBL
CHEMBL1237054
PharmGKB
PA165958411
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Plicamycin
ATC Codes
L01DC02 — Plicamycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentMesothelioma / Neoplasms, Esophageal / Neoplasms, Germ Cell and Embryonal / Neoplasms, Lung / Thymus Neoplasms1
1, 2TerminatedTreatmentEwing's Sarcoma (ES) / Sarcomas1
2RecruitingTreatmentCancer, Breast / Esophageal Cancers / Lung Cancers / Mesothelioma / Neoplasms, Gastrointestinal1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)181.5 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.3 mg/mLALOGPS
logP-0.23ALOGPS
logP2.07ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.49ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area358.2 Å2ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity257.01 m3·mol-1ChemAxon
Polarizability114.41 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6522
Blood Brain Barrier-0.7202
Caco-2 permeable-0.7222
P-glycoprotein substrateSubstrate0.8084
P-glycoprotein inhibitor INon-inhibitor0.7246
P-glycoprotein inhibitor IINon-inhibitor0.7979
Renal organic cation transporterNon-inhibitor0.9474
CYP450 2C9 substrateNon-substrate0.829
CYP450 2D6 substrateNon-substrate0.8772
CYP450 3A4 substrateSubstrate0.6129
CYP450 1A2 substrateNon-inhibitor0.6673
CYP450 2C9 inhibitorNon-inhibitor0.9692
CYP450 2D6 inhibitorNon-inhibitor0.9228
CYP450 2C19 inhibitorNon-inhibitor0.9555
CYP450 3A4 inhibitorNon-inhibitor0.8839
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9814
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9528
BiodegradationNot ready biodegradable0.9779
Rat acute toxicity3.0601 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9888
hERG inhibition (predictor II)Non-inhibitor0.8029
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Oligosaccharides
Alternative Parents
Anthracenes / Naphthols and derivatives / O-glycosyl compounds / Tetralins / Aryl alkyl ketones / 1-hydroxy-4-unsubstituted benzenoids / Oxanes / Beta-hydroxy ketones / Acyloins / Vinylogous acids
show 8 more
Substituents
Oligosaccharide / Anthracene / Glycosyl compound / 1-naphthol / O-glycosyl compound / Tetralin / Aryl ketone / Aryl alkyl ketone / 1-hydroxy-4-unsubstituted benzenoid / Benzenoid
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
anthracycline antibiotic, carbohydrate-containing antibiotic, aureolic acid (CHEBI:31856)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Fox KR, Howarth NR: Investigations into the sequence-selective binding of mithramycin and related ligands to DNA. Nucleic Acids Res. 1985 Dec 20;13(24):8695-714. [PubMed:2934687]
  2. Lombo F, Menendez N, Salas JA, Mendez C: The aureolic acid family of antitumor compounds: structure, mode of action, biosynthesis, and novel derivatives. Appl Microbiol Biotechnol. 2006 Nov;73(1):1-14. Epub 2006 Sep 30. [PubMed:17013601]
  3. Hampshire AJ, Fox KR: The effects of local DNA sequence on the interaction of ligands with their preferred binding sites. Biochimie. 2008 Jul;90(7):988-98. doi: 10.1016/j.biochi.2008.01.001. Epub 2008 Jan 11. [PubMed:18226601]

Drug created on September 14, 2010 10:21 / Updated on November 09, 2017 03:56