Plicamycin
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MedKoo CAT#: 100740

CAS#: 18378-89-7

Description: Plicamycin, also known as mithramycin or Mithramycin A is a n antibiotic isolated from the bacterium Streptomyces plicatus with antineoplastic activity. Plicamycin binds to the minor groove of DNA at GC-rich sites, resulting in inhibition of RNA synthesis; this agent also inhibits mRNA expression, resulting in a reduction in protein synthesis. In addition, plicamycin may inhibit bone resorption by down regulating transcription of c-src, an oncogene involved in bone metabolism and resorption.


Chemical Structure

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Plicamycin
CAS# 18378-89-7

Theoretical Analysis

MedKoo Cat#: 100740
Name: Plicamycin
CAS#: 18378-89-7
Chemical Formula: C52H76O24
Exact Mass: 1084.47265
Molecular Weight: 1085.14
Elemental Analysis: C, 57.56; H, 7.06; O, 35.38

Price and Availability

Size Price Availability Quantity
1.0mg USD 220.0 2 Weeks
5.0mg USD 600.0 2 Weeks
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Synonym: aureolic acid; mithramycin. US brand name: Mithracin. Foreign brand name: Mithracine. Abbreviation: MTH. Code names: A2371; PA144

IUPAC/Chemical Name: (2S,3S)-3-((1S,3S,4R)-3,4-dihydroxy-1-methoxy-2-oxopentyl)-2-(((2S,4R,5R,6R)-4-(((2S,4R,5R,6R)-4-(((2S,4S,5R,6R)-4,5-dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6-(((2S,4R,5R,6R)-4-(((2S,4R,5S,6R)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-8,9-dihydroxy-7-methyl-3,4-dihydroanthracen-1(2H)-one

InChi Key: CFCUWKMKBJTWLW-WZIVUMCRSA-N

InChi Code: 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

SMILES Code: O=C1[C@@H](O[C@H]2C[C@@H](O[C@H]3C[C@@H](O[C@H]4C[C@](C)(O)[C@H](O)[C@@H](C)O4)[C@H](O)[C@@H](C)O3)[C@H](O)[C@@H](C)O2)[C@H]([C@H](OC)C([C@@H](O)[C@H](O)C)=O)CC5=C1C(O)=C6C(O)=C(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)=CC6=C5

Appearance: solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in water.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in water.

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1085.14 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Dutcher JP, Coletti D, Paietta E, Wiernik PH. A pilot study of alpha-interferon and plicamycin for accelerated phase of chronic myeloid leukemia. Leuk Res. 1997 May;21(5):375-80. PubMed PMID: 9225062.

2: Kennedy BJ, Torkelson JL. Long-term follow-up of stage III testicular carcinoma treated with mithramycin (plicamycin). Med Pediatr Oncol. 1995 May;24(5):327-8. PubMed PMID: 7700186.

3: Wimalawansa SJ. Dramatic response to plicamycin in a patient with severe Paget's disease refractory to calcitonin and pamidronate. Semin Arthritis Rheum. 1994 Feb;23(4):267. PubMed PMID: 8009249.

4: Yamreudeewong W, Henann NE, Fazio A, Rangaraj U. Possible severe thrombocytopenia associated with a single dose of plicamycin. Ann Pharmacother. 1992 Nov;26(11):1369-73. PubMed PMID: 1477439.

5: Thürlimann B, Waldburger R, Senn HJ, Thiébaud D. Plicamycin and pamidronate in symptomatic tumor-related hypercalcemia: a prospective randomized crossover trial. Ann Oncol. 1992 Sep;3(8):619-23. PubMed PMID: 1450043.

6: Fang K, Koller CA, Brown N, Covington W, Lin JR, Ho DH. Determination of plicamycin in plasma by radioimmunoassay. Ther Drug Monit. 1992 Jun;14(3):255-60. PubMed PMID: 1412612.

7: Papineschi F, Carulli G, Petrini M. Plicamycin-hydroxyurea association in chronic granulocytic leukemia and multidrug resistance. Haematologica. 1991 Jul-Aug;76(4):349. PubMed PMID: 1686602.

8: Loughner JE, Olek C. Comment: plicamycin infusion. DICP. 1991 Feb;25(2):215. PubMed PMID: 1829288.

9: Antimi M, Masi M, Delannoy A, Ferrant A, Doyen C, Debusscher L, Delwiche F, Stryckmans P, Papa G. The plicamycin and hydroxyurea combination chemotherapy for chronic granulocytic leukemia in myeloid transformation. Haematologica. 1990 Sep-Oct;75(5):443-6. PubMed PMID: 2151448.

10: Mutch RS, Hutson PR, Lewinsky DB. Plicamycin: bolus or infusion? DICP. 1990 Sep;24(9):885-6. PubMed PMID: 2148046.



Additional Information

Mithracin (plicamycin) is a yellow crystalline compound which is produced by a microorganism, Streptomyces plicatus. Mithracin is available in vials as a freeze-dried, sterile preparation for intravenous administration. Each vial contains 2500 mcg (2.5 mg) of Mithracin with 100 mg of mannitol and sufficient disodium phosphate to adjust to pH 7. After reconstitution with sterile water for injection, the solution has a pH of 7. The drug is unstable in acid solutions with a pH below 4. Mithracin is an antineoplastic agent. It has an empirical formula of C52H76O24