Vindesin
methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
Grundinformationen
- CAS
53643-48-4- Standard-SMILES
CC[C@]1(O)C[C@@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C)[C@H]3[C@@](O)(C(N)=O)[C@H](O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1- InChIKey
HHJUWIANJFBDHT-ZVTSDNJWSA-N- Summenformel
- C43H55N5O7
- Durchschnittliche Molmasse
- 753,9 g/mol
- Monoisotopische Masse
- 753,41014911
Überblick
Vinblastine derivative with antineoplastic activity against cancer. Major side effects are myelosuppression and neurotoxicity. Vindesine is used extensively in chemotherapy protocols (antineoplastic combined chemotherapy protocols).
Namen und Bezeichner
- Bevorzugter Name
- methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
- IUPAC
- methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylate
- Lokaler Name
- Vindesin
- Englischer Name
- Desacetylvinblastineamide
- Summenformel
- C43H55N5O7
- Molmasse
- 753.93
Namen und Synonyme
methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraene-13-carboxylateVincaleukoblastine, 23-amino-O(sup 4)-deacetyl-23-demethoxy-methyl (13S,15R,17S)-13-[(1R,9R,10S,11R,12R,19R)-10-carbamoyl-12-ethyl-10,11-dihydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-17-hydroxy-1,11-diazatetracyclo[13.3.1.0^{4,12}.0^{5,10}]nonadeca-4(12),5(10),6,8-tetraene-13-carboxylateR-VindesineVINDESINE [INN]VINDESINE [MI]VINDESINE [HSDB]VINDESINE [USAN]Vindesinum [INN-Latin]UNII-RSA8KO39WHVindesina [INN-Spanish]VINDESINE [VANDF]
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,7
- Polarare Oberfläche (TPSA)
- 165 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 55
- Formalladung
- 0
- Komplexität
- 1.570
Experimentelle und physikochemische Eigenschaften
Melting Point230-232 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- 230 · 230-232°
- Dichte
- 1.41 · 1.41±0.1 g/cm3(Predicted)
- pka
- pKa (DMF 66%) 5.39, 7.36; (H2O) 6.04, 7.67(at 25℃)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- ridadr
- 1544
- hazard_class
- 6.1(a)
- packing_group
- II
- Giftige Stoffe Daten
- 53643-48-4(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Protein Binding65-75%
Pharmacodynamics
Vindesine is indicated for the treatment of acute lymphocytic leukemia of childhood that is resistant to vincristine and non-oat cell lung cancer. Vindesine causes the arrest of cells in metaphase mitosis. It is three times more potent than vincristine and nearly 10 times more potent than vinblastine in causing mitotic arrest in <i>in vitro</i> studies at doses designed to arrest from 10 to 15% of the cells in mitosis. Vindesine and vincristine are approximately equipotent at dose levels that arrest 40 to 50% of the cells in mitosis. Unlike vinblastine, vindesine produces very few postmetaphase cells. Vindesine has demonstrated activity in patients who have relapsed while receiving multiple-agent treatment that included vincristine.
Mechanism of ActionVindesine acts by causing the arrest of cells in metaphase mitosis through its inhibition tubulin mitotic funcitoning. The drug is cell-cycle specific for the S phase.
Biological Half-Life24 hours.
Metabolism/MetabolitesHepatic
Anwendungen
VerwendenAntineoplastic.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
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