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Actinomycin D

Actinomycin D Structure
Actinomycin D
  • CAS No.50-76-0
  • Chemical Name:Actinomycin D
  • CBNumber:CB8853701
  • Molecular Formula:C62H86N12O16
  • Formula Weight:1255.42
  • MOL File:50-76-0.mol
Actinomycin D Property
  • Melting point 251-253 °C
  • Boiling point 848°C (rough estimate)
  • Density 1.0757 (rough estimate)
  • refractive index 1.5700 (estimate)
  • Flash point 87℃
  • storage temp. 2-8°C
  • solubility ethanol, DMSO: Stable in aqueous solutions at 2-8 °C.soluble
  • form powder
  • pka 8.94±0.70(Predicted)
  • color red, powder
  • optical activity [α]/D alpha: 28/D (Rotation: -315 degrees (c=0.25% in methanol))
  • biological source Streptomyces sp.
  • Water Solubility SOLUBLE
  • Merck 13,2828
  • BRN 605235
  • Stability Stable, but light sensitive, especially in dilute solution. Incompatible with strong acids, strong bases, strong oxidizing agents. Combustible.
  • CAS DataBase Reference 50-76-0(CAS DataBase Reference)
  • EWG's Food Scores 4
  • NCI Dictionary of Cancer Terms actinomycin D; Cosmegen; dactinomycin
  • FDA UNII 1CC1JFE158
  • NCI Drug Dictionary Cosmegen
  • ATC code L01DA01
  • Proposition 65 List Actinomycin D
  • IARC 3 (Vol. 10, Sup 7) 1987
  • EPA Substance Registry System Actinomycin D (50-76-0)
  • UNSPSC Code 12352209
  • NACRES NA.76
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H300-H350-H360FD
  • Precautionary statements P201-P202-P264-P270-P280-P301+P310
Actinomycin D Price More Price(16)
  • Brand: Sigma-Aldrich(India)
  • Product number: A9415
  • Product name : Actinomycin D
  • Purity: from Streptomyces sp., suitable for cell culture, ≥95%
  • Packaging: 2MG
  • Price: ₹7772.35
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: A9415
  • Product name : Actinomycin D
  • Purity: from Streptomyces sp., suitable for cell culture, ≥95%
  • Packaging: 5MG
  • Price: ₹17785.48
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: A9415
  • Product name : Actinomycin D
  • Purity: from Streptomyces sp., suitable for cell culture, ≥95%
  • Packaging: 10MG
  • Price: ₹34704.95
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: SBR00013
  • Product name : Actinomycin D, Ready Made Solution
  • Purity: from Streptomyces sp., 2?mg/mL in DMSO
  • Packaging: 1ML
  • Price: ₹15388.1
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: A9415
  • Product name : Actinomycin D
  • Purity: from Streptomyces sp., suitable for cell culture, ≥95%
  • Packaging: 25MG
  • Price: ₹54103.35
  • Updated: 2022/06/14
  • Buy: Buy

Actinomycin D Chemical Properties,Usage,Production

  • Description Actinomycin D (50-76-0) is a cyclopeptide antibiotic and intercalating transcription inhibitor with anti-neoplastic activity. Potent inhibitor of RNA polymerase.1?Induces apoptosis in a variety of cancer cell lines2,3via the intrinsic pathway4.? Upregulates proapoptotic PUMA and downregulates Bcl-2 mRNA in peripheral blood lymphocytes.5
  • Chemical Properties red crystalline powder
  • Chemical Properties Actinomycin D is a combustible, bright red crystalline solid.
  • Originator Cosmegen,Merck Sharp and Dohme,US,1965
  • Uses An antineoplastic antibiotic that inhibits cell proliferation by forming a stable complex with DNA and blocking the movement of RNA polymerase which interferes with DNA-dependent RNA synthesis. Induces apoptosis. Potent antitumor agent.
  • Uses Antibiotic substance belonging to the actinomycin complex, produced by several Streptomyces spp. Antineoplastic
  • Uses antineoplastic, intercalating agent
  • Uses Actinomycin D is the most studied member of a family of unique bicyclic depsipeptides produced by several Streptomyces species. The depsipeptides are linked by a heterocyclic benzoxazone "anchor" that gives the metabolites a highly distinctive red/orange colour. Actinomycin D exhibits potent antibiotic and antitumour activity via DNA intercalation leading to the inhibition of nucleic acid synthesis. Tumour cell death has been demonstrated to occur by apoptosis.
  • Definition ChEBI: Actinomycin D is an actinomycin. It has a role as a mutagen.
  • Indications Dactinomycin (actinomycin D, Cosmegen) is one of a family of chromopeptides produced by Streptomyces. It is known to bind noncovalently to double-strand DNA by partial intercalation, inhibiting DNA-directed RNA synthesis. The drug is most toxic to proliferating cells, but it is not specific for any one phase of the cell cycle. Resistance to dactinomycin is caused by decreased ability of tumor cells to take up and retain the drug, and it is associated with cross-resistance to vinca alkaloids, the anthracyclines, and certain other agents (multidrug resistance).
  • Manufacturing Process An incubated culture of Actinomyces antibioticus was prepared using a medium consisting of 1% tryptone-peptone, 0.5% starch, 0.2% K2HPO4, 0.2% NaCl and 0.25% agar in distilled water, grown at a temperature of approximately 25° to 35°C, the incubation being complete after 6 to 10 days. 50 liters of this incubated culture are extracted approximately six times with ether, using 20 liters of ether for each extraction.
    The final extract is faintly pale yellow in color, whereas the previous extracts are orange. The combined ether extracts are concentrated to dryness and about 3 grams of a reddish-brown residue is obtained. The residue is stirred with approximately 400 cc of petroleum ether for two to three hours, the solvent decanted and the residue treated again with approximately 400 cc of petroleum ether. A pale yellow oil constituting crude actinomycin B is recovered by evaporation from the petroleum ether.
    The dark petroleum ether insoluble residue is dissolved in 1 liter of benzene with gentle heating. Usually a small amount of black amorphous material remains undissolved and is filtered off. The benzene solution is permitted to drop through a chromatographic tower (60 x 5 cm) packed with aluminum oxide (according to Brockman). The pigment is readily adsorbed. The column is washed with about 1 liter of benzene during which operation very little migration of the color bands occurs.
    The column is then washed with benzene-acetone solution (15:85) whereby a chromatogram develops. By continued washing, light yellow colored pigments pass out of the column. When the main band (orange-red) reaches the lower end of the column, a solution of 30:70 acetone-benzene is passed through the column. The latter solvent elutes the pigment and when the eluate is very pale in color, washing is discontinued.
    The eluate is concentrated to dryness under reduced pressure, taken up in 25 cc of hot acetone, filtered, and diluted with ether. The pigment which crystallizes as red-brick colored platelets is essentially pure but may be recrystallized if desired from hot ethyl acetate. An analysis of the product showed C = 59.01; H = 6.81; N = 13.38.
  • brand name Cosmegen (Ovation).
  • Therapeutic Function Cancer chemotherapy
  • General Description Bright red rhomboid prisms or red powder.
  • General Description Dactinomycin is available in vials containing 0.5 mg of drugfor reconstitution in sterile water for IV administration Thisantibiotic is most effective in the treatment of rhabdomyosarcomaand Wilms tumor in children as well as in the treatmentof choriocarcinoma, Ewing sarcoma, Kaposi sarcoma, andtesticular carcinoma. The pharmacokinetics of dactinomycinhas not been well characterized, but it appears to concentratein nucleated blood cells. The agent is 5% to 15% plasmaprotein bound and is excreted mostly unchanged in urineand bile. Other metabolites have not been characterized.The terminal elimination half-life is 30 to 40 hours.Myelosuppression is dose limiting with both leucopenia andthrombocytopenia being the most likely presentation. Nauseaand vomiting occur shortly (2 hours) after treatment and maybe severe. Mucositis and diarrhea also result from irritation ofthe GI tract. Hair loss is commonly associated with the agentas is hyperpigmentation of the skin and erythema.
  • Air & Water Reactions Water soluble.
  • Reactivity Profile Actinomycin D can react with strong oxidizing agents, strong acids and strong bases.
  • Fire Hazard Flash point data for Actinomycin D are not available. Actinomycin D is probably combustible.
  • Biological Activity Anti-neoplastic antibiotic. Inhibits RNA polymerase and is a potent inducer of apoptosis.
  • Mechanism of action Dactinomycin is cleared rapidly from plasma, does not enter the brain, is not appreciably metabolized or protein bound, and is gradually excreted in both bile and urine.Virtually no drug is detected in CSF.
  • Clinical Use Dactinomycin is used in curative combined treatment of Wilms’ tumor, Ewing’s sarcoma, rhabdomyosarcoma, and gestational choriocarcinoma. It is active in testicular tumors, lymphomas, melanomas, and sarcomas, although its use in most of these malignancies has been supplanted by other agents.
  • Side effects The major side effects of dactinomycin are severe nausea, vomiting, and myelosuppression. Mucositis, diarrhea, alopecia, and radiation recall reactions may occur. The drug is immunosuppressive and carcinogenic.
  • Potential Exposure An antibiotic product from streptomyces, used as anticancer and veterinary drug
  • Veterinary Drugs and Treatments Dactinomycin has been used as adjunctive treatment of lymphoreticular neoplasms, bone and soft tissue sarcomas, and carcinomas in small animals. It appears to have low efficacy against most carcinomas and sarcomas. It is being investigated as a part of protocols for rescue therapy for canine lymphomas.
  • Drug interactions Potentially hazardous interactions with other drugs
    Antipsychotics: increased risk of agranulocytosis with clozapine - avoid.
    Cytotoxics: increased risk of hepatotoxicity with vincristine.
    Vaccines: risk of generalised infections with live vaccines - avoid.
  • Metabolism Intravenous doses of dactinomycin are rapidly distributed with high concentrations in bone marrow and nucleated cells. It undergoes only minimal metabolism and is slowly excreted in urine and bile. 15% is eliminated by hepatic metabolism. Approximately 30% of the dose was recovered in the urine and faeces in 1 week.
  • storage +4°C
  • Shipping UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
  • Purification Methods It crystallises as bright red rhombic crystals from absolute EtOH or from MeOH/EtOH (1:3). It will also crystallise from EtOAc/cyclohexane (m 246-247o dec), CHCl3/pet ether ( m 245-246o dec), and EtOAc/MeOH/*C6H6 (m 241-243o dec). Its solubility in MeCN is 1mg/mL. [] D varies from -296o to -327o (c 0.2, MeOH). max (MeOH) 445, 240nm (log  4.43, 4.49), max (MeOH, 10N HCl, 1:1) 477nm (log  4.21) and max (MeOH, 0.1N NaOH) 458, 344, 285 (log  3.05, 4.28, 4.13). It is HIGHLY TOXIC, light sensitive and anti-neoplastic. [Bullock & Johnson, J Chem Soc 3280 1957, Beilstein 27 III/IV 9642.]
  • Incompatibilities Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.
  • References 1) Wagner?et al.(2013)?RNA Polymerase II acts as an RNA-dependent RNA polymerase to extend and destabilize a non-coding RNA ; EMBO J.?32?781 2) J. Kleeff?et al.?(2000)?Actinomycin D induces apoptosis and inhibits growth of pancreatic cancer cells; Int. J. Cancer,?86?399 3) Kasim?et al.?(2013)?Live fluorescence and transmission-through-dye microscopic study of actinomycin D-induced apoptosis and apoptotic volume decrease?; Apoptosis,18?521 4) Liu?et al.?(2016)?Actinomycin D enhances killing of cancer cells by immunotoxin RG7787 through activation of the extrinsic pathway of apoptosis; Proc. Natl. Acad. Sci. USA,?113?10666 5) Kalousec?et al.?(2007)?Actinomycin D upregulates proapoptotic protein Puma and downregulates Bcl-2 mRNA in normal peripheral blood lymphocytes; Anticancer Drugs,?18?763 6) Matsuzaka?et al. (2016)?Characterization and functional analysis of extracellular vesicles and muscle-abundant miRNA in C2C12 myocytes and Mdx mice; PLoS One11(12)?e0167811 [Focus Biomolecules Citation]
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Actinomycin D Spectrum
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