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Doxorubicin hydrochloride
DOX · DOXORUBICIN HCL · ADR · Doxorubicin HCI · DOX HCl · CAELYX · DOX HYDROCHLORIDE · ADRIAMYCIN HYDROCHLORIDE
Identifikatoren & physikalische Daten
| CAS No. | 25316-40-9 |
|---|---|
| Summenformel | C27H29NO11.ClH |
| Durchschnittliche Molmasse | 580 g/mol |
| Monoisotopische Masse | 579,15073846 g/mol |
| 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-RUELKSSGSA-N |
| PubChem CID | 443939 |
| ChEMBL | CHEMBL359744 |
| ChEBI | CHEBI:31522 |
| EC No. | 246-818-3 |
| DTXSID | DTXSID3030636 |
| Lokaler Name | Doxorubicin hydrochloride |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 206 |
|---|---|
| H-Brücken-Donoren | 7 |
| H-Brücken-Akzeptoren | 12 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 40 |
| Formalladung | 0 |
| Komplexität | 977 |
| Löslichkeit | Soluble (NTP, 1992)Soluble in DMSO at 100 mg/mlvery poorly soluble in ethanolsoluble in water at 10 mg/ml with slight warming.Soluble in water. |
| Human Drugs | Breast FeedingLactationMilk, HumanAntineoplastic AgentsAnthracyclinesAntibiotics, AntineoplasticTopoisomerase II InhibitorsFDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Schmelzpunkt | 399 to 401 °F (Decomposes) (NTP, 1992)216 °C (dec.)(lit.) |
| Physical Description | Adriamycin hydrochloride appears as orange-red thin needles. Aqueous solutions yellow-orange at acid pHs, orange-red at neutral pHs, and violet blue over pH 9. (NTP, 1992) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | pKa 8.25±0.60 (Uncertain)8.43±0.70 (Uncertain)11.9±0.4 (Uncertain)12.95±0.1 (Uncertain)13.8±0.70 (Uncertain) |
| Aggregatzustand | solid |
| Farbe | orange to dark red |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,3439 |
| BRN | 4229251 |
| Stabilität | Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months. |
| InChIKey | MWWSFMDVAYGXBV-RUELKSSGSA-N |
| SMILES | Cl[H].COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO |
| CAS Datenbank | 25316-40-9(CAS DataBase Reference) |
| EPA chemische Informationen | Doxorubicin hydrochloride (25316-40-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (77.8%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 158 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityDevelopmental ToxicityReproductive ToxicityAdriamycin hydrochloride: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | This compound is probably combustible. (NTP, 1992) |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| Reactivity Profile | Amines, like adriamycin hydrochloride, are weak chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. |
| Air and Water Reactions | Water soluble. |
| Hazard Classes and Categories | Acute Tox. 4 (77.8%) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical carbon dioxide, foam or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Personal Protective Equipment (PPE) | MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Doxorubicin hydrochloridevLess-DILI-concern3Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| F | 10-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN2811 |
| Zollcode | 29419090 |
| RTECS-Nr. | QI9295900 |
| R-Sätze (R) | 45-22-40-26/27/28-36/38 |
| Toxizität | LD50 i.v. in mice: 21.1 mg/kg (Bertazzoli, 1970) |
| Gefahrensymbole | T,T+,Xi |
| Sicherheitshinweise (S) | 53-45-36/37/39-22-7/9 |
| Gefahrenklasse | 6.1Acute Tox. 4 OralCarc. 1BMuta. 1BRepr. 1B |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Verwenden
Doxorubicin hydrochloride (adriamycin hydrochloride) is an antitumour agent that has been formulated as a salt to achieve higher water solubility. While the salt shares the same pharmacological properties as doxorubicin free base, its greater water solubility may offer advantages in some in vitro applications. Physicochemical properties and chromatographic behaviour will depend on whether the pH is buffered. In non-pH controlled systems the free base and salt may behave differently.