Galantamin
GALANTAMINE · Galantamin · Galantamina · (4aS,6R,8aS)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol · Razadyne · Galanthamine-d3 HCl · (4aS,8aS)-4a,5,9,10,11,12-Hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6β-ol · Jilkon
Identifikatoren & physikalische Daten
| CAS No. | 357-70-0 |
|---|---|
| Summenformel | C17H21NO3 |
| Durchschnittliche Molmasse | 287,35 g/mol |
| Monoisotopische Masse | 287,15214353 g/mol |
| SMILES | COc1ccc2c3c1OC1CC(O)C=CC31CCN(C)C2 |
| InChIKey | ASUTZQLVASHGKV-UHFFFAOYSA-N |
| PubChem CID | 3449 |
| ChEMBL | CHEMBL1623394 |
| ChEBI | CHEBI:91735 |
| DTXSID | DTXSID70859345 |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 41,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 21 |
| Formalladung | 0 |
| Komplexität | 440 |
| Arzneimittel | Pharmaceuticals |
| Schmelzpunkt | 119-1210C |
| Siedepunkt | 429.65°C (rough estimate) |
| Dichte | 1.0662 (rough estimate) |
| Brechungsindex | 1.5022 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | ≥14.37 mg/mL in DMSO≥14.43 mg/mL in H2O with gentle warming≥45 mg/mL in EtOH with gentle warming |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | pKa 8.32 (Uncertain) |
| Farbe | White to off-white |
| InChI | InChI=1S/C17H21NO3/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17/h3-6,12,14,19H,7-10H2,1-2H3/t12-,14-,17-/m0/s1 |
| InChIKey | ASUTZQLVASHGKV-JDFRZJQESA-N |
| SMILES | N1(C)CC2=CC=C(OC)C3O[C@]4([H])[C@@](C=C[C@H](O)C4)(C2=3)CC1 |
| CAS Datenbank | 357-70-0(CAS DataBase Reference) |
| NIST chemische Informationen | Galantamin(357-70-0) |
Sicherheit & Vorschriften
| Toxizität | LD50 intraperitoneal in mouse: 10mg/kg |
|---|---|
| Gefahrstoffdaten | 357-70-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Galantamine is an Amaryllidaceae alkaloid which is first obtained from the plant of snowdrop (Galanthus nivalis), and nowadays, it’s extracted from the plants of Narcissus and Galanthus species or obtained from chemosynthesis. In many areas in Europe such as Bulgaria, eastern Turkey, and the Caucasus, the plants of Galanthus are native species. But its earliest pharmaceutical applications are seldom known. Plaitakis and Duvoisin hypothesized that “moly” in ancient Homer’s epic might be snowdrops. In Homer’s epic Odyssey, “moly” was used as an antidote by Odysseus against Circe’s poisonous drugs. To be used as an antidote may be the plants of Galanthus’ oldest medicinal records. But there is not much evidence for that. There is little evidence of the traditional application of the plants of Galanthus, and it is certain that until the Second World War, the plants of Galanthus and other genera of Amaryllidaceae were not frequently used in European drugsItalian scholar Iannello studied Pancratium illyricum L., an Amaryllidaceae species endemic to Sardinia, and isolated a new galantamine-type alkaloid in its leaves. This new galantamine-type compound exhibited a pronounced invitro AChE inhibitory activity (IC50 = 3.5±1.1 μM) in comparison with the reference standard galantamine hydrobromide (IC50=1.5±0.2μM)
Occurrence
Galanthamine is a bulb plant found throughout the world.
History
In the early 1950s, Soviet Union’s scientists started modern medicine research of galantamine. In 1951, the Soviet Union’s pharmacologist Mashkovsky and Kruglikova-Lvova firstly proved its AChE-inhibiting properties, which was published in the paper. In 1957, the Bulgarian pharmacologist Paskov etal. found that the plants of Galanthus were the richest sources of galantamine, which opened a way for its commercial development by the company Sopharma in Bulgaria. Galantamine hydrobromide was launched into market under the trade name Nivalin. Initially, Nivalin was used in anesthesia to antagonize the effects of non-depolarizing muscle relaxants, and since then, it was rapidly introduced in other areas of medicineGalantamine hydrobromide was launched into market for the indication of mild to moderate Alzheimer’s disease firstly in 1995, developed by Sanochemia Pharmaceuticals. In the United States, galantamine hydrobromide was developed by Janssen Pharmaceuticals, a subsidiary of Johnson & Johnson, and was listed under the trade name Razadyne in 2001. So far, galantamine hydrobromide has been marketed in more than 20 countries and regions, such as the United States, Europe, and Japan.
Verwenden
A selective acetylcholinesterase inhibitor. Useful for the treatment of Alzheimer's disease.