HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-DL-glutaminsure
dl-amethopterin · dl-MTX · 6-mtx(dl) · NSC 117356 · AKOS 93273 · -)AMETHOPTERIN · dl-methotrexate · (±)Amethopterin
![Molekülstruktur von N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-DL-glutaminsure](/img/chemical/4112.png)
Identifikatoren & physikalische Daten
| CAS No. | 51865-79-3 |
|---|---|
| Summenformel | C20H22N8O5 |
| Durchschnittliche Molmasse | 454,4 g/mol |
| Monoisotopische Masse | 454,1713158 g/mol |
| SMILES | CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc1 |
| InChIKey | FBOZXECLQNJBKD-UHFFFAOYSA-N |
| PubChem CID | 4112 |
| ChEMBL | CHEMBL426 |
| ChEBI | CHEBI:93775 |
| EC No. | 262-213-7 |
| DTXSID | DTXSID40859034 |
| Lokaler Name | N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-DL-glutaminsure |
Chemische & physikalische Eigenschaften
| XLogP | -1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 211 |
| H-Brücken-Donoren | 5 |
| H-Brücken-Akzeptoren | 12 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 33 |
| Formalladung | 0 |
| Komplexität | 704 |
| Arzneimittel | Pharmaceuticals |
| Schmelzpunkt | 195 °C (dec.)(lit.) |
| Dichte | 1.536±0.06 g/cm3(Predicted) |
| Lagerbedingungen | −20°C |
| Löslichkeit | H2O: Add a minimal amount of 0.1 L NaOH to solubilize, then dilute in neutral buffer or saline. Diluted stock is stable for 1week refrigerated and for 1month frozen at20°C. |
| pKa (Säurekonstante) | 3.47±0.10(Predicted) |
| Aggregatzustand | powder |
| Farbe | yellow |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Treatment | Administer charcoal as a slurry. Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion (generally within 1 hour). Protect airway by placement in Trendelenburg and left lateral decubitus position or by endotracheal intubation. Control any seizures first. Glucarpidase has been used intravenously in combination with thymidine and leucovorin to treat methotrexate toxicity. (T36) |
| Gesundheitliche Auswirkungen | A small percentage of patients develop hepatitis, and there is an increased risk of pulmonary fibrosis where dry cough can be an important sign. The higher doses of methotrexate often used in cancer chemotherapy can cause toxic effects to the rapidly-dividing cells of bone marrow and gastrointestinal mucosa. The resulting myelosuppression and mucositis are often prevented (termed Leucovorin "rescue"- as this is the folic acid based drug used) (L1079). |
| Expositionspfade | Inhalation (A314)dermal (A314)intravenous (A314) Oral absorption is dose dependent in adults and leukemic pediatric patients. In adults, peak serum levels are reached within one to two hours. At doses of 30 mg/m^2 or less, methotrexate is generally well absorbed with a mean bioavailability of 60%. At doses greater than 80 mg/m^2, the absorption of the doses is significantly less due to a saturation effect. |
| Toxizitätsübersicht | Methotrexate anti-tumor activity is a result of the inhibition of folic acid reductase, leading to inhibition of DNA synthesis and inhibition of cellular replication. The mechanism involved in its activity against rheumatoid arthritis is not known. |
| Signs and Symptoms | Symptoms of overdose include bone marrow suppression and gastrointestinal toxicity. |
| Carcinogen Classification | 3, not classifiable as to its carcinogenicity to humans. (L135) |
| Toxicity Data | LD50: 43 mg/kg (Oral, Rat) (A308) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 1544 6.1/PG 2 |
| RTECS-Nr. | MA1224100 |
| R-Sätze (R) | 61-25-36/38-23/24/25 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 53-26-36/37-45-36/37/39 |
Anwendungen & Verwendung
Verwenden
Amethopterin is an antineoplastic, antirheumatic, folic acid antagonist