Doxorubicin hydrochloride
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Doxorubicin hydrochloride
structure -
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CAS No:
25316-40-9
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Formula:
C27H29NO11.ClH
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Chemical Name:
Doxorubicin hydrochloride
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Synonyms:
5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-,hydrochloride (1:1),(8S,10S)-;Adriamycin,hydrochloride;5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,hydrochloride,(8S-cis)-;5,12-Naphthacenedione,10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-,hydrochloride,(8S,10S)-;Doxorubicin hydrochloride;Adriamycin;Adriacin;Adriblastina RD;Adriblastina;Adriblastin;ADR;DOX HCl;FI 6804;ADM hydrochloride;Hydroxydaunorubicin hydrochloride;FI 106;Adriablastina CS;Lipo-Dox;Adrosal;Ameisu hydrochloride;Myocet liposomal;Doxolipad;Caelyx pegylated liposomal;Doxorubicin-TEVA;Doxorubicin-LANS
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CAS No:
Description
Doxorubicin hydrochloride is a cytotoxic anthracycline antibiotic for the treatment of multiple cancers. The possible mechanisms by which doxorubicin acts in the cancer cell are intercalation into DNA and disruption of topoisomerase-II-mediated DNA repair.
Characteristics
206.07000
1.50360
Orange-Red Crystalline Solid
204-205 °C
810.3ºC at 760 mmHg
443.8ºC
H2O: 10 mg/mL, clear, red-orange
2-8ºC
9.64E-28mmHg at 25°C
LD50 i.v. in mice: 21.1 mg/kg (Bertazzoli, 1970)
Safety Information
NONH for all modes of transport
3
R45; R22
S53-S45-S36/37/39-S22-S7/9
QI9295900
T+
Stable at room temperature in closed containers under normal storage and handling conditions.
P201-P305 + P351 + P338-P308 + P313
H302-H315-H319-H350
Doxorubicin hydrochloride Use and Manufacturing
1. Used as an antineoplastic
2. Strong fluorescent dye intercalating into DNA. Antitumour antibiotic. Effect of adriamycin on heart mitochondrial DNA. Inhibitor of reverse transcriptase and RNA polymerase; immunosuppressive agent.
3. Antibacterial;DNA intercalant
4. 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.
5. Doxorubicin hydrochloride (adriamycin hydrochloride) is an antitumor 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.
6. Doxorubicin is an anthracycline antitumor antibiotic that inhibits DNA topoisomerase II by inducing double-stranded DNA breaks. By intercalating within DNA, doxorubicin inhibits nucleic acid synthesis and induces apoptosis by inducing the accumulation of the p53 tumor suppressor protein.[Cayman Chemical]
Computed Properties
Molecular Weight:543.5
XLogP3:1.3
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:5
Exact Mass:543.17406074
Monoisotopic Mass:543.17406074
Topological Polar Surface Area:206
Heavy Atom Count:39
Complexity:977
Defined Atom Stereocenter Count:6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Unspecified
Registered Holders
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DZD (HEZE) PHARMACEUTICAL CO LTD
Active
United States
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PHARMACIA AND UPJOHN CO WHOLLY OWNED SUB PFIZER INC
Active
United States
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Gemini PharmChem Mannheim GmbH
Active
Germany
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