Tamiflu
Osteltamivir phosphate · Oseltamivir Phosphate (200 mg) · (3R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate · (3R,4R,5S)-ethyl 4-acetaMido-5-aMino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate · SOT · Oselt · CS-1978 · Oseltamivir PH
Identifikatoren & physikalische Daten
| CAS No. | 204255-11-8 |
|---|---|
| Summenformel | C16H31N2O8P |
| Durchschnittliche Molmasse | 410,4 g/mol |
| Monoisotopische Masse | 410,18180258 g/mol |
| SMILES | CCOC(=O)C1=C[C@@H](OC(CC)CC)[C@H](NC(C)=O)[C@@H](N)C1.O=P(O)(O)O |
| InChIKey | PGZUMBJQJWIWGJ-ONAKXNSWSA-N |
| PubChem CID | 78000 |
| ChEMBL | CHEMBL1200340 |
| ChEBI | CHEBI:7799 |
| DTXSID | DTXSID0044230 |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 168 |
|---|---|
| H-Brücken-Donoren | 5 |
| H-Brücken-Akzeptoren | 9 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 27 |
| Formalladung | 0 |
| Komplexität | 468 |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntiviral AgentsNeuraminidase InhibitorsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Schmelzpunkt | 196-198°C |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | H2O: soluble30mg/mL, clearSoluble in water (75 mM) |
| Aggregatzustand | powder |
| Farbe | white to beige |
| BCS Class | 1 (CLogP), 3 (LogP) |
| Hauptanwendungen | pharmaceuticalpharmaceutical small molecule |
| InChI | InChI=1/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)191-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)(H3,1,2,3,4)/t13-,14+,15+/s3 |
| InChIKey | PGZUMBJQJWIWGJ-IFAKAUOZSA-N |
| SMILES | [C@@H]1(OC(CC)CC)C=C(C[C@H](N)[C@H]1NC(=O)C)C(=O)OCC.OP(O)(O)=O |&1:0,10,12,r| |
| CAS Datenbank | 204255-11-8(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Oseltamivir phosphatevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
|---|---|
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| Zollcode | 2924299500 |
| Gefahrenklasse | IRRITANTAquatic Chronic 3Eye Irrit. 2Skin Sens. 1 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Oseltamivir phosphate (Tamiflu) was launched in the US and Switzerland for the treatment of influenza infections by all common strain viruses. It is an oral anti-viral drug approved for the treatment of acute, uncomplicated influenza in patients 2 weeks of age and older whose flu symptoms have not lasted more than two days. This product is approved to treat Type A and B influenza; however, the majority of patients included in the studies were infected with type A, the most common in the U.S. Efficacy of Tamiflu in the treatment of influenza in subjects with chronic cardiac disease and/or respiratory disease has not been established.
Verwenden
Oseltamivir phosphate (Tamiflu) is a competitive neuraminidase inhibitor. The prodrug oseltamivir phosphate (Tamiflu) is itself not virally effective; however, once in the liver, it is converted by natural chemical processes, hydrolysed hepatically to its
Herstellung & Synthese
synthetische
Oseltamivir phosphate (Tamiflu) has been synthesized from cis-2,3-bis(hydroxymethyl)aziridine. After protection of the cis-2,3-bis(hydroxymethyl)aziridine with a Boc group, desymmetrization provided a chiral aziridine, which was a key intermediate to install the required stereogenic center containing a nitrogen atom. Allylation and ring closing metathesis are the key reactions to obtain the cyclic product that was successfully converted to the desired oseltamivir phosphate. DOI: 10.1021/jo3015853It can also be obtained by a novel 12-step synthesis from (-)-quinic acid.