50-76-0
50-76-0 structure
- Name: Actinomycin D
- Chemical Name: actinomycin D
- CAS Number: 50-76-0
- Molecular Formula: C62H86N12O16
- Molecular Weight: 1255.417
- Catalog: API Antineoplastic agents Antibiotic antineoplastic agents
- Create Date: 2018-02-04 08:00:00
- Modify Date: 2024-01-02 18:29:21
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Actinomycin D inhibits DNA repair with an IC50 of 0.42 μM.
| Name | actinomycin D |
|---|---|
| Synonyms |
dactinomycin
2-Amino-N,N'-bis[(6S,9R,10S,13R,18aS)-6,13-diisopropyl-2,5,9-trimethyl-1,4,7,11,14-pentaoxohexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-4,6-dimethyl-3-oxo-3H-phenoxazine-1,9-dicarboxamide noxazin-1,9-dicarboxamid 2-amino-4,6-diméthyl-3-oxo-N,N'-bis[(6S,9R,10S,13R,18aS)-2,5,9-triméthyl-6,13-bis(1-méthyléthyl)-1,4,7,11,14-pentaoxohexadécahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatétraazacyclohexadécin-10-yl]-3H-phé Actinomycin AIV 2-Amino-4,6-dimethyl-3-oxo-N,N'-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxohexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-3H-phe 3H-phenoxazine-1,9-dicarboxamide, 2-amino-N1,N9-bis[(6S,9R,10S,13R,18aS)-hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-4,6-dimethyl-3-oxo- Actinomycin X1 2-amino-4,6-dimethyl-3-oxo-N,N'-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxohexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-3H-phenoxazine-1,9-dicarboxamide EINECS 200-063-6 MFCD00070921 2-amino-4,6-dimethyl-3-oxo-N,N'-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-1,4,7,11,14-pentaoxo-6,13-di(propan-2-yl)hexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-3H-phenoxazine-1,9-dicarboxamide MERACTINOMYCIN Actinomycin I1 Acto-D Actinomycin D Chounghwamycin B 2-Amino-4,6-dimethyl-3-oxo-N,N'-bis[(6S,9R,10S,13R,18aS)-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxohexadecahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-3H-phenoxazin-1,9-dicarboxamid Dilactone actinomycin D acid 2-amino-4,6-diméthyl-3-oxo-N,N'-bis[(6S,9R,10S,13R,18aS)-2,5,9-triméthyl-6,13-bis(1-méthyléthyl)-1,4,7,11,14-pentaoxohexadécahydro-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatétraazacyclohexadécin-10-yl]-3H-phénoxazine-1,9-dicarboxamide 3H-phenoxazine-1,9-dicarboxamide, 2-amino-N,N'-bis[(6S,9R,10S,13R,18aS)-hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-4,6-dimethyl-3-oxo- ACT Oncostatin K noxazine-1,9-dicarboxamide 3H-Phenoxazine-1,9-dicarboxamide, 2-amino-N,N-bis[(6S,9R,10S,13R,18aS)-hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohexadecin-10-yl]-4,6-dimethyl-3-oxo- 3H-Phenoxazine-1,9-dicarboxamide, 2-amino-N,N-bis[(6S,9R,10S,13R,18aS)-hexadecahydro-2,5,9-trimethyl-6,13-bis(1-methylethyl)-1,4,7,11,14-pentaoxo-1H-pyrrolo[2,1-i][1,4,7,10,13]oxatetraazacyclohe
 xadecin-10-yl]-4,6-dimethyl-3-oxo- |
| Description | Actinomycin D inhibits DNA repair with an IC50 of 0.42 μM. |
|---|---|
| Related Catalog | |
| Target |
IC50: 0.42 μM (DNA repair)[1] |
| In Vitro | Actinomycin D is an inhibitor of DNA transcription and replication[1]. Actinomycin D markedly reduces the vascular smooth muscle cells (SMC) proliferation via the inhibition of BrdU incorporation at 80 nM. This is further supported by the G1-phase arrest using a flowcytometric analysis. Actinomycin D is extremely potent with an inhibitory concentration IC50 at 0.4 nM, whereas the lethal dose LD50 is at 260 microM. The protein expression levels of proliferating cell nuclear antigen (PCNA), focal adhesion kinase (FAK), and Raf are all suppressed by Actinomycin D. Extracellular signal-regulated kinases (Erk) involved in cell-cycle arrest are found to increase by Actinomycin D[2]. |
| In Vivo | The pluronic gel containing 80 nM and 80μM Actinomycin D is applied topically to surround the rat carotid adventitia, the thickness of neointima is substantially reduced (45 and 55%, respectively)[2]. Mice in the Actinomycin D and fludarabine group lives significantly longer than the control group with P values of <0.001 and 0.007, respectively. Interestingly, single treatment with Actinomycin D is superior to fludarabine regarding overall survival (P=0.026)[3]. |
| Kinase Assay | Actinomycin D is co-incubated for 3 h at 30°C with a reaction mixture containing: 120 mg of a whole-cell extract of HeLa cells, 70 mM KCl, 0.4 mM each of dGTP, dCTP, dATP, and digoxygenylated-dUTP in reaction buffer containing 40mM Hepes-KOH (pH 7.6), 5 mM MgCl2, 0.5 mM Dithiotreitol, 2 mM EGTA, 10 mM phosphocreatine, 50 mg/mL creatine phosphate, and 360 mg/mL of bovine serum albumin. During this reaction, DNA damage is recognized and the excised patches are replaced by neosynthesized DNA fragments. Throughout this DNA synthesis, digoxygenylated-dUMPs are incorporated. The DNA repair reaction is stopped by three washes[1]. |
| Animal Admin | Mice[3] The original Eμ-TCL1a transgenic mice have been backcrossed to C57BL/6 mice for >9 generations.The C57BL/6 wild-type mice are engrafted with tumor cells from Eμ-TCL-1 transgenic mice. The percentage of CD5+/CD19+ cells in the peripheral blood is routinely checked in mice by taking blood from the tail vein and analyzing it via flow cytometry. When the percentage of tumor cells in the peripheral blood reached 40-60%, treatment is started. Actinomycin D (0.06 mg/kg by 10 days) is applied daily via i.p. injections. |
| References |
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 1386.0±65.0 °C at 760 mmHg |
| Melting Point | 251-253 °C |
| Molecular Formula | C62H86N12O16 |
| Molecular Weight | 1255.417 |
| Flash Point | 792.1±34.3 °C |
| Exact Mass | 1254.628418 |
| PSA | 359.98000 |
| LogP | -4.03 |
| Vapour Pressure | 0.0±0.3 mmHg at 25°C |
| Index of Refraction | 1.656 |
| Stability | Stable, but light sensitive, especially in dilute solution. Incompatible with strong acids, strong bases, strong oxidizing agents. Combustible. |
| Water Solubility | SOLUBLE |
Synonym:Dactinomycin Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
Risk Phrases: 28 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW
Very toxic if swallowed.Light sensitive. Potential Health Effects Eye: May cause severe eye irritation. May cause eye injury. Skin: May cause skin sensitization, an allergic reaction, which becomes evident upon re-exposure to this material. Ingestion: May be fatal if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Inhalation: May cause respiratory tract irritation. May cause effects similar to those described for ingestion. Inhalation may produce coughing, nausea, and pulmonary edema. Chronic: Repeated exposure may cause sensitization dermatitis. Section 4 - FIRST AID MEASURES Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Skin: Get medical aid if irritation develops or persists. Wash clothing before reuse. Flush skin with plenty of soap and water. Destroy contaminated shoes. Ingestion: Call a poison control center. If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid if cough or other symptoms appear. Do NOT use mouth-to-mouth resuscitation. Notes to Physician: Treat symptomatically and supportively. Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Wash area with soap and water. Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Storage: Do not store in direct sunlight. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.) Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Use only under a chemical fume hood. Exposure Limits CAS# 50-76-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Powder Color: red Odor: none reported pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 245-252C Autoignition Temperature: Not applicable. Flash Point: 241 deg C ( 465.80 deg F) Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: 250 deg C Solubility in water: In methanol Specific Gravity/Density: Molecular Formula: C62H86N12O16 Molecular Weight: 1255.5 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials, light, dust generation, excess heat. Incompatibilities with Other Materials: Strong oxidizing agents, strong bases, strong acids Hazardous Decomposition Products: Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 50-76-0: AU1575000 LD50/LC50: CAS# 50-76-0: Oral, mouse: LD50 = 13 mg/kg; Oral, mouse: LD50 = 20 mg/kg; Oral, rat: LD50 = 7200 ug/kg. Carcinogenicity: Actinomycin D - California: carcinogen, initial date 10/1/89 Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Products which are considered hazardous for supply are classified as Special Waste and the disposal of such chemicals is covered by regulations which may vary according to location. Contact a specialist disposal company or the local waste regulator for advice. Empty containers must be decontaminated before returning for recycling. Section 14 - TRANSPORT INFORMATION IATA No information available. IMO No information available. RID/ADR No information available. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: T+ Risk Phrases: R 28 Very toxic if swallowed. Safety Phrases: S 1 Keep locked up. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 50-76-0: 3 Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 50-76-0 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 50-76-0 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A |
| Symbol |
GHS06 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H300 |
| Precautionary Statements | P264-P301 + P310 |
| Personal Protective Equipment | Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges |
| Hazard Codes | T+:Verytoxic; |
| Risk Phrases | R28;R40;R61 |
| Safety Phrases | S53-S36/37/39-S45-S1-S36/37-S28-S22 |
| RIDADR | UN 3462 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | AU1575000 |
| Packaging Group | II |
| Hazard Class | 6.1(a) |
| HS Code | 29419000 |
| Precursor 4 | |
|---|---|
| DownStream 0 | |
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| HS Code | 29419000 |
|---|