(8S-cis)-10-[(3-Amino-2,3,6-tridesoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacen-5,12-dionhydrochlorid
Epirubicin Hydrochloride
Grundinformationen
- CAS
56390-09-1- Standard-SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1.Cl- InChIKey
MWWSFMDVAYGXBV-FGBSZODSSA-N- Summenformel
- C27H30ClNO11
- Durchschnittliche Molmasse
- 580 g/mol
- Monoisotopische Masse
- 579,15073846
Überblick
Epirubicin hydrochloride is an anthracycline. It has a role as an antineoplastic agent.
Namen und Bezeichner
- Bevorzugter Name
- Epirubicin Hydrochloride
- IUPAC
- (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
- Lokaler Name
- (8S-cis)-10-[(3-Amino-2,3,6-tridesoxy-α-L-arabino-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxynaphthacen-5,12-dionhydrochlorid
- Englischer Name
- Epirubicin hydrochloride
- Summenformel
- C27H30ClNO11
- Molmasse
- 579.98
Namen und Synonyme
Epirubicin hydrochloride56390-09-1Epirubicin HClFarmorubicinaIMI-28NSC-759195WP-69722966TX7J5DTXSID508602975,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S-cis)-Pharmorubicin PfsRefChem:55118
Weitere Namen anzeigen
EbeweAdrialCS-1396Epirubin HCIEpirubicin EbeweFarmorubicin-RTU(8s-cis)-rochloridEpirubicinHc,LEp5,Epirubicin HCl API
Hydrochloride, EpirubicinIMI28DTXCID001475450(2S,4S)-4-(3-Amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy)-2,5,12-trihydroxy-2-hydroxyacetyl-7-methoxy-1,2,3,4-tetrahydrotetracene-6,11-dione monohydrochloride(8S-cis)-10-((3-Amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione Hydrochloride3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside HydrochlorideEllenceMFCD00941448
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 206 Ų
- H-Brücken-Donoren
- 7
- H-Brücken-Akzeptoren
- 12
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 40
- Formalladung
- 0
- Komplexität
- 977
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Anthracyclines; Antibiotics, Antineoplastic; Topoisomerase II Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section225.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 185 °C · 185°C dec.
- Flammpunkt
- 443.8 ℃ · 443.8℃
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- Löslichkeit
- 100 mM, · Soluble in DMSO to 100mM, or in ethanol to 10mM
- Aggregatzustand
- powder
- pka
- 11.33 · 11.33 (pKa₃)(Temp: 25 °C; Solvent: Sodium chloride 0.9)
- Farbe
- red to deep red
- Stabilität
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.
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 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 130 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
5,12-Naphthacenedione, 10-(3-amino-2,3,6-trideoxy-.alpha.-L-arabino-hexopyranosyl)oxy-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hydrochloride, (8S,10S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (99.2%)
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Epirubicin hydrochloride
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- wgk
- 3
- hs_code
Chemie und Industrie
Pharmakologische Informationen
FDA Pharmacological Classification
EPIRUBICIN HYDROCHLORIDE
Anthracycline Topoisomerase Inhibitor [EPC]; Topoisomerase Inhibitors [MoA]; Anthracyclines [CS]
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
Anwendungen
BeschreibungEpirubicin hydrochloride is an antitumor antibiotic which is epimeric with doxorubicin a t the 4’-position of the amino sugar moiety. It has shown utility in the treatment of mammary, gastric, colorectal, pulmonary and ovarian carcinomas, as well as malignant lymphoma and melanoma and soft tissue sarcoma. It is reported to be less sardiotoxic than doxorubicin.
VerwendenUsed as an antineoplastic
Zugehörige Reaktionen
2
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