Vinorelbine Tartrate
Grundinformationen
- CAS
125317-39-7- Standard-SMILES
CCC1=C[C@@H]2CN(C1)Cc1c([nH]c3ccccc13)[C@@](C(=O)OC)(c1cc3c(cc1OC)N(C)[C@H]1[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]4(CC)C=CCN5CC[C@]31[C@@H]54)C2.O=C(O)[C@H](O)[C@@H](O)C(=O)O.O=C(O)[C@H](O)[C@@H](O)C(=O)O- InChIKey
CILBMBUYJCWATM-PYGJLNRPSA-N- Summenformel
- C53H66N4O20
- Durchschnittliche Molmasse
- 1.079,1 g/mol
- Monoisotopische Masse
- 1.078,42704051
Überblick
Vinorelbine Tartrate is the ditartrate salt of a semisynthetic vinca alkaloid derived from the leaves of the periwinkle plant (Vinca rosea) with antineoplastic properties. Vinorelbine binds to tubulin, thereby inhibiting tubulin polymerization into microtubules and spindle formation and resulting in apoptosis of susceptible cancer cells. Inhibition of mitotic microtubules correlates with antitumor activity, whereas inhibition of axonal microtubules seems to correlate with vinorelbine's neurotoxicity. Compared to related vinca alkaloids, vinorelbine is more selective against mitotic than axonal microtubules in vitro, which may account for its decreased neurotoxicity. This agent is also a radiation-sensitizing agent. (NCI04)
Namen und Bezeichner
- Bevorzugter Name
- Vinorelbine Tartrate
- IUPAC
- bis((2R,3R)-2,3-dihydroxybutanedioic acid);methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(12S,14R)-16-ethyl-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
- Englischer Name
- Vinorelbine tartrate
- Summenformel
- C53H66N4O20
- Molmasse
- 1079.11
Namen und Synonyme
Vinorelbine tartrateVinorelbine ditartrateKW-2307Vinorelbine liposomal253GQW851QVinorelbine (as tartrate)Vinorelbine BitartrateLiposomal vinorelbine tartrateVinorelbine tartrate (1:2)TLC178TLC-178Eunades
Weitere Namen anzeigen
NAVELBINENVBVinorelbin Tartratec’-norvincaleukoblastine,3’,4’-didehydro-4’-dioxy-,(r-(r*,r*))-2,3-dihydroxyVINORELBINE TARTRATE USP STANDARD3′,4′-Didehydro-4′-deoxy-C′-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt], 5′-Noranhydrovinoblastine tartrate, KW-2307, NVB, Navelbine tartrate(2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylicacidmethylester
DTXSID5047825Nor-5'-anhydrovinblastine ditartrateC'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-, (R-(R*,R*))-2,3-dihydroxybutanedioate (1:2) (salt)Vinorelbine DitartarateNSC608210CHEBI:32296BiovelbinNavelbine ditartrate
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 364 Ų
- H-Brücken-Donoren
- 10
- H-Brücken-Akzeptoren
- 23
- Frei drehbare Bindungen
- 16
- Schwere Atome
- 77
- Formalladung
- 0
- Komplexität
- 1.820
Experimentelle und physikochemische Eigenschaften
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 181 · 181-183°C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 2 O: · H2O: 10 mg/mL
- Aggregatzustand
- powder
- Farbe
- off-white
- Wasserlöslichkeit
- 2 O: · H2O: 10mg/mL
- Stabilität
- Light Sensitive, Temperature Sensitive
- InChIKey
- PMDHUNWDGZSEMN-WTUOTUPFSA-N
- CAS Datenbank
- 125317 · 125317-39-7(CAS DataBase Reference)
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
H301 (88.9%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P260, P264, P264+P265, P270, P280, P301+P316, P302+P352, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 63 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 2 (88.9%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Vinorelbine tartrate
Ambiguous-DILI-concern
3
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1544PSN1 6.1 / PGII
- hs_code
- 29339900
- risk_code
- 43
- hazard_code
- Xi
- safety_code
- 26-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Skin Sens. 1
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
Verwendung und Herstellung
UsesUse (kg) in USA (2002): 3
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionChEBI: The L-(+)-tartrate salt of vinorelbine.
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