Rubitecan
Grundinformationen
- CAS
104195-61-1- Standard-SMILES
CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1- InChIKey
VHXNKPBCCMUMSW-FQEVSTJZSA-N- Summenformel
- C20H15N3O6
- Durchschnittliche Molmasse
- 393,3 g/mol
- Monoisotopische Masse
- 393,09608521
Überblick
Rubitecan is a pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin. It has a role as an antineoplastic agent, a prodrug and an EC 5.99.1.2 (DNA topoisomerase) inhibitor. It is a delta-lactone, a tertiary alcohol, a C-nitro compound, a pyranoindolizinoquinoline and a semisynthetic derivative.
Namen und Bezeichner
- Bevorzugter Name
- Rubitecan
- IUPAC
- (19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
- Englischer Name
- Rubitecan
- Summenformel
- C20H15N3O6
- Molmasse
- 393.35
Namen und Synonyme
Rubitecan9-Nitrocamptothecin91421-42-09-nitro-20(S)-camptothecinOrathecinCamptogenRFS 2000RFS-2000NitrocamptothecinrubitecanumH19C446XXB9-nitro-20-(S)-camptothecin
Weitere Namen anzeigen
9-Nitrocellulose camptothecine9-NCOratheciRUBETICANRubitecane9-NITRO-CPT
DTXSID7046752CHEBI:90225RFS20009-nitro-(20S)-camptothecinDTXCID50267521H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4-hydroxy-10-nitro-, (4S)-(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo(11.8.0.0^(2,11).0^(4,9).0^(15,20))henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione(19S)-19-ethyl-19-hydroxy-8-nitro-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
Datenbank-Bezeichner
- CAS
104195-61-1、91421-42-0- PubChem CID
- 472335
- DTXSID
DTXSID7046752
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,8
- Polarare Oberfläche (TPSA)
- 126 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 1
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 861
Experimentelle und physikochemische Eigenschaften
LogP2.16
Physikochemische Eigenschaften
- Schmelzpunkt
- 182 · 182-186°C
- Siedepunkt
- 816.3 · 816.3±65.0 °C(Predicted)
- Dichte
- 1.63 · 1.63
- Flammpunkt
- 106 ℃ · 106℃
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- DMSO, Chloroform, Methanol
- Aggregatzustand
- Solid
- pka
- 11.16 · 11.16±0.20(Predicted)
- Farbe
- Yellow
- Biologische Quelle
- synthetic (organic)
- Merck
- 14 · 14,8288
- InChI
- InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1
- InChIKey
- VHXNKPBCCMUMSW-FQEVSTJZSA-N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P264, P270, P280, P301+P317, P318, P319, P330, 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.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
- hs_code
- 29399990
- RTECS-Nr.
- UQ0493300
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of ActionRubitecan prevents DNA from unwinding during replication via DNA topoisomerase 1, therefore interfering with tumor growth.
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds that inhibit the activity of DNA TOPOISOMERASE I.
Anwendungen
BeschreibungRubitecan is a DNA topoisomerase I inhibitor. It inhibits DNA topoisomerase I and increases the fraction of supercoiled DNA in a cell-free assay in a concentration-dependent manner. Rubitecan inhibits the growth of A121 ovarian and H460 lung cancer cells (IC50s = 4 and 2 nM, respectively). It also inhibits the growth of doxorubicin-susceptible and -resistant MCF-7 breast cancer cells (IC50s = 2 and 3 nM, respectively). Rubitecan (4 mg/kg twice per week) reduces tumor growth in a U937 leukemia mouse xenograft model.
Ergänzende Hinweise
DefinitionChEBI: A pyranoindolizinoquinoline that is camptothecin in which the hydrogen at position 9 has been replaced by a nitro group. It is a prodrug for 9-aminocamptothecin.
Zugehörige Reaktionen
7
Notizen zur Verbindung
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