plicamycin

Trade name: mithracin

Small moleculeapproved

Approved

May 5, 1970

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. — NCATS

Clinical trial activity

3 trials · 2 clinical orgs · 1 marketing orgs

Phase 1
2
Phase 2
3
Phase 3
0
Phase 4
0

Earliest trial started May 1, 2012 (NCT01610570)

Timeline

1970s

  1. May 5, 1970

    Pfizer — Earliest FDA Approval

  2. May 5, 1970

    Pfizer — NDA Organization

2010s

  1. Jan 1, 2012

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2012

    Earliest Phase 2 Sponsor(trial)

Indications

Mechanism of action

  • DNAINHIBITOR

    DNA inhibitor

Approval history

  • approvedPriority reviewMay 5, 1970

Chemistry & pharmacology

Loading structure…

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
Mol. weight
1085.1454 g/mol
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Parenteral
Availability
Discontinued

Oral

No

Parenteral

Yes

Topical

No

Sources

Also known as

  • a-2371
  • a-2371
  • aureolic acid
  • aureolic acid
  • aureolic acid
  • mithracin
  • mithracin
  • mithracin
  • mithracin
  • mithramycin
  • mithramycin
  • mithramycin
  • mithramycin
  • mithramycin
  • mithramycin
  • mithramycin
  • mithramycin a
  • mithramycine
  • mithramycine
  • mithramycinum
  • mithramycinum
  • mithramycinum
  • mitramycin
  • pa-144
  • pa-144
  • plicamycin
  • plicamycin
  • plicamycin
  • plicamycin
  • plicamycin
  • plicamycin
  • plicamycin
  • plicamycin
  • plicamycine
  • plicamycine
  • plicamycinum
  • plicamycinum
  • plicatomycin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT02859415Phase 1/Phase 2 (Phase 2)Jul 21, 2016National Cancer Institute (NCI)
NCT01624090Phase 2Jun 12, 2012National Cancer Institute (NCI)
NCT01610570Phase 1/Phase 2 (Phase 2)May 1, 2012National Cancer Institute (NCI), National Institutes of Health (NIH)
Showing 3 of 3 trials
Page 1 / 1

Organizations

Research & Development (2)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
National Cancer Institute (NCI)Government3312012
National Institutes of Health (NIH)Government1012012
2 organizations
Page 1 / 1

Marketing (2)

OrganizationOrg typeRelationshipDate
PfizerFor profitSYNMay 5, 1970
PfizerFor profitNDAMay 5, 1970