N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide
Amsacrine
CAS: 51264-14-3
Molecular Formula: C21H19N3O3S
N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide - Names and Identifiers
| Name | Amsacrine |
| Synonyms | CI-880 Amekrin Amsidyl Amsakrin Amsacrine M-AMSA, HCL M-AMSA HYDROCHLORIDE 4'-(9-Acridinylamino)methanesulfon-m-anisidide N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide N-[4-(Acridin-9-ylamino)-3-(methyloxy)phenyl]methanesulfonamide |
| CAS | 51264-14-3 |
| EINECS | 257-094-3 |
| InChI | InChI=1/C22H20N2O3S/c1-27-22-14-16(24-28(2,25)26)12-11-15(22)13-19-17-7-3-5-9-20(17)23-21-10-6-4-8-18(19)21/h3-12,14,24H,13H2,1-2H3 |
N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide - Physico-chemical Properties
| Molecular Formula | C21H19N3O3S |
| Molar Mass | 393.46 |
| Density | 1.2205 (rough estimate) |
| Melting Point | 230-240 °C |
| Boling Point | 563.0±60.0 °C(Predicted) |
| Flash Point | 313.5°C |
| Vapor Presure | 4.07E-14mmHg at 25°C |
| pKa | 8.55±0.10(Predicted) |
| Storage Condition | 2-8°C(protect from light) |
| Refractive Index | 1.6740 (estimate) |
| Physical and Chemical Properties | Acute toxicity LD50 male mice, female mice (mg/m2):810,729 oral. Amsacrine Hydrochloride: C2Lh19N3O3S? HCl. Crystalline, melting point 197-199 °c. Acute toxicity LD50 mice (mg/kg): about 60 intraperitoneal injection. Amsacrine hanesulfonate: C21H19N3O3S? CH3SO3H. Crystallization, melting point 292~293 deg C. Acute toxicity LD50 mice (mg/kg): About 24 intraperitoneal injection. |
N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide - Risk and Safety
| UN IDs | 3249 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in male, female CDF1 mice: 810 mg/m2; 729 mg/m2 orally (Pavkov) |
N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 2.542 ml | 12.708 ml | 25.416 ml |
| 5 mM | 0.508 ml | 2.542 ml | 5.083 ml |
| 10 mM | 0.254 ml | 1.271 ml | 2.542 ml |
| 5 mM | 0.051 ml | 0.254 ml | 0.508 ml |
Last Update：2024-01-02 23:10:35
N-[4-(acridin-9-ylmethyl)-3-methoxyphenyl]methanesulfonamide - Reference Information
| (IARC) carcinogen classification | 2B (Vol. 76) 2000 |
| pharmacological action and mechanism of action | amacridine has broad-spectrum anti-tumor activity, and the mechanism of action is similar to anthracyclines. Anacridine binds to DNA and has an effect on the pairing of adenine and thymine base pairs. It mainly inhibits DNA synthesis, has obvious inhibitory effect on S and G2 cells, and has little effect on RNA synthesis. |
| pharmacokinetics | amacridine is poorly absorbed orally and is usually administered intravenously. It is metabolized in the liver and excreted by bile. The permeability to the blood-cerebrospinal fluid barrier is poor, and the cerebrospinal fluid content is less than 20% of the blood concentration. |
| adverse reactions | 1, mainly bone marrow suppression, which is dose-limiting toxicity. When the dosage reaches 90~120 mg/m2, platelets and leukopenia can occur. 2, common gastrointestinal reactions, dose-related. Low to moderate nausea and vomiting often occur. When the total dose reaches 750 mg/m2 or higher, mucositis is easy to occur. 3, heart, liver and nerve toxicity is mild, and ventricular arrhythmia may occur in some patients. Allergic reactions and seizures are rare, often accompanied by alopecia. |
| use | acridine anticancer drug, a cell inhibitor. The principle of action is similar to that of anthracyclines. It is mainly used for the treatment of leukemia with acute lymphocytes and bone marrow cells. |
| Production method | o-methoxy p-nitroaniline reacts with acid chloride to protect the amidation of the amino group, reduce the nitro group to the amino group, acylate the amino group with methanesulfonyl chloride to form a methanesulfonamide group, and then selectively hydrolyze to remove the protecting group on the 1 amino group, and finally react with 9-chloracridine to obtain acridine. |
| category | toxic substances |
| toxicity classification | highly toxic |
| acute toxicity | oral administration-mouse LD50: 53.42 mg/kg; Abdominal cavity-mouse LD50: 15.47 mg/kg |
| flammability hazard characteristics | flammability; heat decomposition releases toxic nitrogen oxides, sulfur oxide smoke; drug side effects; nausea, vomiting, bone marrow lesions, etc. |
| storage and transportation characteristics | warehouse ventilation and low temperature drying |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:41:03
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